Well Dave called me the following day saying how about we go for that beer tonight, sure sounds good to me I replied ok great, he gives me the name of this place I'd never heard of before so he said just meet me at my place and we can drive over together or you can follow me. Yeah, that’s fine send me your address and I'll meet you there. Hey I have a little favor to ask oh what's that Dave, well you looked really hot last night, and I loved your tits, and ah one day in the office Lori showed me pictures of you on her phone fully dressed, and holy fuck did you look smokin would you mind he asked dressing like that for me, wait she did what oh fuck who the hell else did she show all of the girls in the office?
No, no its cool relax only me it’s cool. nobody there knows or suspects anything trust me she’s way too cool for that. Oh, shit! Man, you had my mind racing there for a minute, dam what the hell would I wear to the company Christmas party, we both laughed Dave saying now that would be cool. Dave unknowingly relaxed me enough to say sure why not what I’ll wear them for you, he laughed yeah but I'm not a boob man remember, yeah ok sure you’re not no problem. Dave said great than it’s a date, I thought to myself it’s a date, not just a couple of guys going for a few beers, I figured what the fuck why not I’d love to experience going out on a real date as a woman, thinking to myself yeah well he's only seen me in my bra and panties I'll really give him something to look at.
Lori was planning on going out with one of her friends and (her sister to keep her out of trouble) to see a movie so it would work out well. I went home showered shave really close, shaved my legs Lori and I regularly go for couples Brazilian bikini waxes so I'm pretty much hairless and smooth just like she likes it and I love the look and the feeling as well. I slipped my cock into a gaff that Lori and her girlfriend had bought for me to wear when they had me dress fem for them something that has become a regular part of life around the ranch as we say. As I’m sure you’re aware a gaff is a special panty type device so to speak where you slip your cock into a sheath and its pulled up between your legs affixing to the back of the waistband so with your cock tucked between your legs it gives your front a much more anatomically female appearance this one of several but I choose it because it has a vagina what the girls also liked it prevents me from getting a hard on a sure giveaway for any guy trying to pass as a woman I then proceeded to get dressed as Brandy my feminine self.
I put on a pair of red and black lace trimmed satin bikini panties with a matching bra and had to decide if I was going to wear a garter belt and stocking or pantyhose or thigh high hose decisions, decisions so thinking the patent leather mini skirt I had in mind it would be much better choice to go with a pair of black thigh highs. I chose a black satin blouse that Lori had bought for me during one of her shopping sprees topped off with a black leather jacket.
(Since accepting my long-dormant crossdressing due in part to her new found bi-sexuality she was all in and really immersed herself into encouraging me so what better way but to buy me clothes, clothes that made me look slutty just the way she wanted me to look when I was her bitch but tonight I was going to be Dave’s bitch. She did tell me she had plans to buy me a few tamer outfits for around the house but somehow, she hadn't gotten around to it hmm I wonder why)
I left my blouse unbuttoned just enough to see a glimpse of my bra although the silicone breast forms that were not just a pair of falsies stuffed into the cups of my bra but rather they are high quality that actually glue to the chest so they would stay in place even if I were to go topless they appeared to give me nice full breast. I longed for pair of real tits with ample cleavage and nice perky nipples forever I truly felt I was a woman trapped in a man’s body and deserved to be feminine but Lori drew the line at any sort of implants or anything hinting of female hormones therapy etc., she reminded me that I had a very successful business that I busted my ass for and going to that extreme was just too much which of course she was right hence the reason she did so much research and spent the money on these, which I had several different sizes and shapes variants but tonight for Dave I was a 36D I wanted the extra slutty look. I did my makeup and donned one of the wigs Lori purchased for me I don’t possess the famine skills with a hairbrush and blow-dryer to do my own hair that something the girls do, tonight I was going to be a redheaded slut. There was no doubt in my mind what Dave wanted when he asked me to dress up and after having one hell of a great time the night before I was more than ok with it, actually thought about him fucking me the entire following day even while having sex with Lori I was dreaming of Dave’s big cock and the ass pounding and mouth fucking I was given so I figured I may as well look the part.
I finished my outfit off with a pair of thigh high patent leather boots with platform heels so I could walk without breaking my neck I hadn’t yet mastered pumps or spiked heels but was working on. I owe all what I know about dressing slutty to my wife who outwardly is a very conservative house wife that is until she decides to let her hair down and have fun, even her co-workers said she like has a Jeckle & Hyde personality there is work and Lori who is all business and then there if fun Lori who is a party animal who likes pushing the limits.
I made sure to pack my guy cloths and a few essentials in a gym bag just in case, I am a very passable crossdresser plus going out at night eases fears of being outted. I’ve driven around a few times alone and more than a few with Lori and her live in girlfriend something I used to do with my ex a lot. One night we pulled up to a light and I saw these two guys eyeing us from across the street when we stopped at a light and as it happened I knew one of them, I told Lori and she got all nervous saying what do you want me to do, I said do nothing don’t even look just wait for the light to change and go. She did as instructed and made a few turns here and there looking in the rearview mirror ok I don’t think anyone is following us. I laughed and said I think you watch too many cop shows on TV.
So, I strut my ass through the house checking myself out in one of the full length mirror saying to myself hey I’d fuck you. I made my way through the kitchen and into the garage and throw my bag in my triple black Cadillac CTSV with tinted windows of course...lol I fire the beast up and hit the garage door remote and I’m off for a great night of fun with Mr. Big, I plug the directions to Dave’s place into my GPS about halfway there I decided let me fill up. I pull in and we don’t have self-service where we live, so I wait for the attendant who is checking out my ride to come over and I lower the window asking him to fill it up in my best female voice which isn’t the greatest so I know to keep my words short n to the point. Wow lady you have a really nice car, oh shit it’s got a 6 speed, how fast will it go? Ok so Barney is very chatty, and I don’t feel like giving myself away, so I place my hand up to my throat and whisper sore throat. Oh, ok I’m sorry I just smile thinking don’t you worry I’ll be getting something for my sore throat real soon Dr. Dave’s two ball compound. He finishes up and hands me my receipt and my card saying ok I hope you feel better, I just smiled and blow him a kiss and headed on my way to Dave’s
I pulled into the driveway of a very modest home in what appeared to be a quite middle class neighborhood. I strutted up the walkway in full view of some couple walking their dog who I knew was checking out my ass how could he not. I rang the doorbell and the door opened and there was Dave wearing a cut off sleeveless shirt and a pair of jeans his jaw almost hit the floor as he stood there for a second with his mouth open and finally said holy fuck your even hotter in person. I smiled saying so you’re not a breast man but how do you like mind, with the front door still open he leaned in and planted a kiss on my lips and slipped me some tongue, without stopping he reached for my girls with both hands groping and fondling them God they even feel real. Ah Dave still fondling my tits unless you want to put on a show for your neighbors, oh yeah and he reached for the door with one hand and flings it shut. He whisked me inside and continued to feel me up when before I knew it he stuck his tongue in my mouth and firmly held my arms at my side now I am not a small or weak person but Dave is massive pro-football player size so that combined with the overwhelming feeling of lust I was paralyzed and he knew it, when he broke off the kiss he just smiled saying I knew you wanted that since that night. Maybe he was right or maybe I was just taken by surprise and filled with the lustful thoughts of his big cock inside me since he called. I was breathing heavily and just looked at him returning his kiss we now played tonsil hockey for a few minutes as fondled my tits and grabbed my ass. He firmly grabbed both ass cheeks saying now that’s some ass and I know it’s real. Oh yes, it is but you ought to know that as you violated it smiling at him, we both laughed violated it I said yes it sounds a little more lady like that you fucked me up the ass, so I was walking bowlegged the next day. Oh yeah by the way weren’t you taking me out on a date, oh yeah he laughed how about a couple of drinks here first ok well I could use a good stiff one, glancing at his crotch which was showing the outline of his ample member, he said well if you insist laughing let me get you a drink first. Good idea I replied he returned with a couple of beers and a two shot glasses and a bottle of Tequila. We sat on the couch and did a few shots and had several beers while he asked me a bunch of questions about my crossdressing the how long the whys, etc. and how did I get Lori so into it. Well that was a lot easier than I thought to be honest she has to be one of the kinkiest women I have ever met so to her it was just another way of enjoying kinky sex, I guess plus she is the love of my life and I will do pretty much anything in the world to please her. Hey not for nothing I really don’t mind the questions but talking about my wife right now isn’t doing anything for the mood if you know what I mean. He agreed and we made small talk about this and that and next thing I know is his hand is on my knee and he leans in to kiss me, I willingly accepted his kiss which turned it to more and more, throwing all my resistance and lady like decorum right out the window(lady like my ass I am a true slut no doubt about it. Then our heavy petting session ensued as I felt his hand going further and further up my inner thigh, so I reached for his massive member still hidden in the confines of his jeans and started rubbing it. I knew it had a positive effect on him as he started to squirm a little. His hand kept moving up my thigh till he reached where he expected to find my cock. He started feeling and reaching in my panties and I playfully slapped his hand down sailor I laughed. He picked my skirt up and peeked under saying what the hell. Well DavieI just said I wanted to dress for the occasion figuring I wasn’t going to be the one doing any penetrating but rather the one being penetrated you mean you’re the one who is going to get fucked, I said yes sir now that’s the whole purpose of me being here isn’t it. He laughed and said well I did invite you for a couple of drinks now didn’t I. I laughed and figured it was time for me to go into my slutty prostitute persona one of Lori and Barbies favorites when we role play.
So, you want my ass do you now well it’s going to cost you honey, Dave played right along, oh really now so how much is this going to cost me he asked. I said well depending on what you’re looking, everything baby I want it all he laughed, ok all it is then, for everything plus the house call fee I’d normally get $500 for the night he raised his eyebrows, but seeing as you know Lori you get a special discount and I’ll let you run a tab. He smiled and said well I hear your worth every penny and kissed me I said do we have a deal, he squeezed my tits and said yes baby we have a deal. Ok first let me go freshen up a bit and I got up and excused myself to go use the bathroom. I did have to pee and now I know fully what women have to go through every time nature calls. So, I finished up my business but before I returned, I took a small bottle of lube from my purse and stuck it up my ass and squeezed it filling my anal cavity. I knew all too well what to expect from Dave’s massive cock and that the night before I was pre lubed and pre stretched from Lori’s pounding so I wasn’t taking any chances, I readjusted my gaff not yet owning the type that will allow you to pee without removing it, I pulled up my panties and adjusted myself and pulled out a tube of lipstick from my purse the girls had thoroughly schooled me in the art of applying makeup as they put it they wanted the me to experience the whole package the entire female experience not just putting on a bra and panties. I applied my lipstick and put the tube back in the purse along with my tube of Astroglide our favorite and headed back to my date.
Now not being totally naïve in the ways of dating etc. not wanting to be the victim of a ruffe not that Dave would do that but you never know so nit until I knew that I could trust him 100% was I going to take any chances I grabbed a couple of fresh beers from the frig took a nice big swig and picked up the bottle of Tequila and took a very liberal hit and passed the bottle off to him. I asked Dave if he had any weed but he said no he didn’t but could see if he could score some from his friend, that would be great if you could although I was relaxed but that little something extra would be just what I needed, so he sent his friend a text then he said well it’s time to get what I paid for and he went to unzip his jeans.
I took his hand saying allow me. I dropped to my knees and slowly unzipped his tight fitting jean reaching in for his cock I gently removed it and it practically sprung to life. It seemed bigger than I recalled maybe in part to like I said earlier my lustful desire I began kissing the head of his dick and running my tongue all over the head which was now adorned with the baby pink lipstick I was wearing, one of the things Lori loves to do to me, I was mimicking so many of the things she does and has taught me. Hell, I was taking on her persona. I kept licking him and kissing the head of his cock teasing him so as to make him even harder, I than say on his lap facing him and grinding on his massive cock teasing the hell out of him oh didn’t I tell you a lap dance is part of the package all he could do was smile saying your such a fucking cock teaser. Oh, you have no idea honey as I gyrated on his throbbing member, I could feel it like a big snake was coming out of its hole, yeah looking for mine. I then turned around, so I was facing away from him but lowered myself back onto his cock and continued by bump n grind knowing it was driving him nuts. I then thought ok I’ve teased you enough time to get down to business. I got back down on my knees spreading his legs apart and proceeded to devour his cock, I sucked and slurped and got it slick and glistening from my saliva. I sucked the head of his dick and flicked it with my tongue.
He was moaning and groaning holy shit you give the best head, looking up at him saying oh better than your boyfriend, he laughed and said that bitch can’t hold a candle to you slut.
Oh by the way where is he, I asked. I told him to go back to his mother because he bitched so much ok so he’s not going to come back and get his panties in a bunch, nope not a chance it’s just you and me baby. Good as I engulfed his now rapidly hardening member. As I sucked, I unbuckled his belt and undid the snap on his jeans and teasingly pulled down the zipper. I then grabbed the waistband of his long leg briefs and pulled them and his pants all the way down to his ankles. Now his cock was clear of obstructions and free for me to suck and to lick his balls. I was pumping his shaft as my hand as my head bobbed up and down on his hard cock, I could feel it hit the back of my throat and knew I was going to try to deepthroat him but by his shear length and girth is was not going to be an easy task but I was willing to give it all I had.
So as I continued to slide his cock in and out of my mouth each time I kept going deeper and deeper, taking more of it in each time I did gag somewhat but was not about to give up as long as he wasn’t forcing me I knew I would be ok because I could stop anytime I wanted. Now I had it planned that I would give Dave the best blowjob possible and then give up my ass all things going as I planned in my head on the ride over to is place as the night continued. Dave was moaning saying oh yeah bay that feels so fucking good has anyone ever told you that you suck a mean dick. Ah hmm was my response as I didn’t want to interrupt my pursuit of getting him into my throat. I kept sucking and slurping massaging his balls and stroking his shaft but I for one enjoy a true blowjob no hands are involved it’s all about oral skills. I never appreciated a woman jerking me off into her moth not that it’s a bad thing, but a blowjob involved sucking and stroking is to be done with the mouth and lips. As hard as I tried, I was unable to fit the entire length of his shaft far enough in to reach my throat, but Dave didn’t seem to mind. His breathing was now increasing and his hips starting bucking and I knew he was getting ready to blow his load and I was determined to swallow every single ounce. As his pace quickened and so did his breathing, I increased my speed and sucked him harder and harder until he let out a long loud moan of fuck! Fuck! I’m cumming you slut whore suck my cock bitch. He no sooner got the word bitch out when he began shooting hot ropes of cum in my mouth and I feverishly sucked his cock, as he pumped load after load of hot jizz I suck and swallowed almost every ounce of his cum.
Dave exhaled and relaxed his body, but I continued to suck his cock clean which by now was extra sensitive so much so he almost couldn’t stand it. I had plenty of cum left in my mouth, so I got to my feet and planted a deep French kiss on his lips spitting his cum into his mouth. This took Dave totally by surprise and he attempted to pull away, but I had a firm grip on his head which made him realize any resistance was futile. We kissed for a minute and finally relaxing my grip I pulled away and took a step back and just smiled. So, tell me who gave the better blowjob me or Lori I laughed. His response was holy shit now talk about putting a guy on the spot like I said I am really not into women but man your wife gives one hell of a blowjob. I said yes, she sure does and like she said she taught me everything I know. He laughed saying remind me to thank her. Oh speaking of Lori does she know you’re here he asked, no I said she has no idea she went out for the evening and knowing her she won’t be back till late she’s not out catting around not because she wouldn’t but she’s with her sister and their friend her sister has no idea of her wild side so she will have a pretty boring evening. Ok it’s our secrete then that’s fine, I said oh Dave he looked at me as if to say what you may want to consider taking her up on her offer to fuck her. He looked at me as to say what the fuck. I said listen I’m perfectly fine with you doing her and she does have a hall pass that she has never used but I know her, and I know she wants your cock and will be relentless and not stop until you fuck her brains out ok, I’ll think about it. We both sat on the couch Dave bringing us each a cold one, now he was totally naked he sits down next to me telling me how wild I am I said hey, look who I’m married to and we both laughed. I said ok here is one rule I have you can fuck me in the ass all you want cumming in there is fine too but don’t expect me to put your cock in my mouth after its been in my ass, if you want that you need to wear a condom. He looked at me saying I don’t have any, I reached for my purse on the coffee table pulling out a strip of at least 6 magnum condoms I said a girl has to be prepared especially us working girls.
We both laughed and I grabbed his cock and started playing with it, I stood up saying let me take off my jacket at least, so I stood up and removed it and tossed it on one of the chairs, while I was up I unbuttoned one button of my blouse revealing my bra and not to mention my cleavage Dave was amazed looking at me saying you have real tits as he squeezed one I said not exactly just modern technology a little body makeup and good strong glue, I opened my blouse all the way and said look I even have nipples popping one tit out of its cup. He just looked them over and said amazing. Wow I never would have thought you guys were so into it.
I laughed saying you have no idea we fool everyone. I then said fuck it and removed my blouse and tossed it on a chair now only wearing my bra and skirt and stockings still wearing my boots though. The entire time I was playing with is dick and talking about my tits he even asked if I could fuck with my fake vagina that I said has yet to be tried but I think you’re a wee bit too large for that. As he talked about how kinky we were I could feel his cock beginning to pulse, so I smiled and said well back to business the meters running you know and proceeded to go down on his beautiful piece of man meat putting it in my mouth getting right down to business. It didn’t take very long before Dave was fully erect and ready to get down to business. He stood up and hand me bend over asking me if I was ready. It’s all yours honey. Dave stood behind me slipping my panties to one side and guided his big fat 10 plus inch cock into my pre-lubed ass. His length was not more than I had grown used to over time with Lori using rubber dildos on me, but his girth was incredible he was a big around as a beer can I’m guessing, I was really glad I had thought of the idea. He moaned as she slowly slipped it in inch by inch until he was buried balls deep inside me. He began slowly fucking me in and out pulling it almost the entire length out with the head stretching my sphincter to its limit as he would slide it back in every time he did this I let out a moan and tried my best to control my breathing and relax my body enough to take the fucking Dave was giving me. He continued his slow rhythmic pace and I now met his thrust with my hips pushing back towards him, it didn’t take long before we were in perfect sync, The feeling of him filling me sliding it in and out was beyond euphoric, He reached around and cupped both of my tits as he slammed his balls into my ass cheeks remember what I told them about being glued in place but not to get too carried away, truth be told they are not that easy to remove it does take a little doing so I wasn’t worried about them falling off or popping out onto the floor like by other implants the girls had gotten, yes I said implants Barbie my wife’s girlfriend works in the pharmaceutical industry but has connections with several plastic surgeons all of whom want to fuck her badly but that was something that was never going to happen her pussy belonged to my wife so she scored me actual saline implants they use in breast enhancement but these were far more realistic in all respects and made me feel like a woman, the woman I was meant to be I was getting lost in Dave pounding me, he had both of my tits and popped them out of my bra they were swinging and swaying with every pounding of my ass, this went on for a few minutes I caught my breath saying stop, stop let me put them back in it feels better not the same dilemma as my wife with her all natural 38DD melons having some heft to them but even mine had enough that I could feel the pulling sensation. I no sooner popped them back in Dave continued his pounding of my ass, my long red hair wildly flying about my tits swinging within the confines of my bra being tested to the limit. I was so deep in the trance of my ass being pounded and most of the time I had my eyes closed and would open them when Dave would slap me on my ass first on my skirt covered ass then he had my skirt lifted enough to bare my entire panty covered behind. I hear Dave mutter something and I open my eyes looking right at this guy gawking at me getting fucked silly by Dave. It turned out to be his buddy Richie his weed connections. Well either Dave didn’t lock the door, or he had a key but regardless of how he was now standing with in an arm’s reach of me. I was shocked to say the least but in no position to do anything about it being as Dave had me bent over so far, I couldn’t have straightened up and pulled away even if I tried or was it if I wanted to?
Well Dave never broke stride and kept pounding me in the ass. His friend said hey sorry man I didn’t hey since when are you into chicks. Dave said since I met this bitch, laughing he said this is Bobby stopping short of saying you know Lori’s old man as I was to find out later, he had met my wife once or twice. Oh, wow and the next thing I now is this guy has his cock out Dave says do you mind, I had to say no I’m not ready for this, again I said no! and stopped my hips from meeting Dave’s thrust so he knew I meant business and not wanting to ruin a good thing he said sorry man you gotta go. Having two cocks is probably every cock suckers dream but I wasn’t lying I just was not ready for it, maybe because I was taken by surprise. His friend didn’t hurry up to leave and continued to gawk as I was still getting pounded, finally Dave said you really gotta go dude, and his friend took the hint and left Dave called lock the fucking door asshole. Dave slapped me hard on the ass several times and said now where we he was now pounding my ass hard I could hear his balls slapping against my ass and I got back into the rhythm of us fucking Dave had now been in my ass for a good 20 minutes total and I was really hoping he was getting ready to cum because I was getting really sore. I asked him if he wanted to cum on my face or on my tits figuring jerking him off would be a lot less uncomfortable. No baby I’m getting ready and he started shuttering almost as if his body was convulsing, he started grunting oh fuck! oh fuck yeah baby I’m going to fill your ass with that I felt like a firehouse of hot loads of his cum begin to fill my ass. I stopped my meeting his thrust, but Dave still kept pounding my feverishly I could not only feel my ass squishing but could hear it as well as with every thrust I could hear the sound of his cum which was now overflowing my asshole I was filled beyond capacity. Dave gave me one last mega thrust getting his last once of cum into my ass almost knocking me over onto the floor. He stopped and was breathing heavy holding on to both of my hips he was not about to move until he caught his breath, he said later he needed to hold on to me or he would have fallen flat on his face. I told him I have to get up and it one swift motion Dave pulled his massive cock from my ass not only did it pop from the hydraulic seal of my ass being over filled with his cum, but the size of his giant head leaving my hole wasn’t exactly pleasant feeling it was akin to a hot poker being stuck in my ass, how I didn’t pass out is beyond me. We both collapsed on his couch my ass leaking cum. I told him to go get me a towel at first, he didn’t move right away but I said towel now. I stood up and there was a large cum stain on the couch cushion oh well I thought as I used the towel to clean myself. I said he you made the mess you ought to be the one helping me clean up. He laughed and said gimmie holding out his hand I stood up and he proceeded to clean his cum from me with the towel when all of a sudden, I felt his hands on my hips and his tongue licking my ass. I was thinking ok this isn’t so bad, kind of makes up for shithead not locking the front door. I sat back down fully intending to go at least one maybe two more rounds with Dave when he gets a text fucking asshole he muttered. I looked at him what, my asshole friend couldn’t keep his mouth shut I should have known. Within seconds he get three more texts wanting to know if his date was still there, hey are we having a gangbang he is apologizing to me like no one’s business. I stood up he said please don’t go. I just said I’m outta here I’m not getting gang raped by your friends and forget about fucking my wife your friend ruined a good thing. My plan was to get changed into my regular cloths for the ride home but, no time for that I gather up my stuff fixed my bra and put my blouse back on ran my fingers through my hair thinking it’s time to get the hell out of here before I am the party favor for a bunch of his friends. I said see you around Dave and remember what I said all he could do was sit there with his big now flaccid cock saying he was sorry, well we did have a lot of fun yeah but I planned on having a hell of a lot more fun but your friend fucked it up I said and left I got in my car and headed off not even turning on my lights for a block or two.
I had thought about stopping somewhere to change but decided against it, looking at the clock I figured I still had plenty of time before Lori got home. Well wrong I was not only was she home, but her sisters car was in the driveway, I grabbed my phone and sent her a text is everyone still awake/ She responded yes, we’re having a glass of wine why are you home, I said unlock the French doors in out bedroom. Of course, I get why just come in through the garage I text back French doors unlock now! no need to explain. She excuses herself to go use the bathroom and instead of using the one right off the kitchen she goes into the master bedroom she unlocks the French doors and there I am standing there looking like the whore that I am, thigh high boots mini skirt big tits pushing against my blouse. She laughed and gasped covering her mouth so her sister and their friend would hear her Holy shit what the hell, where you out turning tricks no not exactly let me get out of these clothes and I’ll explain later. She laughed and said oh no you don’t you’re going to stay right here dressed just like you are oh and by the way you look fucking hot and then you’re going to tell me all about it and I am going to fuck your brains out do you understand, reaching in her dresser draw pulling out one of her strap-on’s. Yes, yes who she glared I said yes mistress but what about your siter and your friend oh they are ready to pass out they’ll sleep in the spare room so you sit your pretty little self-right here on the bed and wait for me do you understand looking up at her yes mistress was all I said as she walked out the door back to the kitchen. I waited seated on the bed like a good little sub slave but the entire time I was thinking about the great fucking I had gotten from Dave, maybe I shouldn’t have freaked out, maybe I should have sucked his friends cock, hell most go a life time without ever having a threesome and I literally had it right with in my reach Dammit what a fucking idiot I was. I even could have stuck around to be gang banged by Dave and his friends my head was spinning with all the possible scenario’s. I picked up my phone and sent Dave a text. I’m still pissed but I forgive you lets hook up in a couple of day give my ass a chance to recover. All I got back was the smiley face
No, no its cool relax only me it’s cool. nobody there knows or suspects anything trust me she’s way too cool for that. Oh, shit! Man, you had my mind racing there for a minute, dam what the hell would I wear to the company Christmas party, we both laughed Dave saying now that would be cool. Dave unknowingly relaxed me enough to say sure why not what I’ll wear them for you, he laughed yeah but I'm not a boob man remember, yeah ok sure you’re not no problem. Dave said great than it’s a date, I thought to myself it’s a date, not just a couple of guys going for a few beers, I figured what the fuck why not I’d love to experience going out on a real date as a woman, thinking to myself yeah well he's only seen me in my bra and panties I'll really give him something to look at.
Lori was planning on going out with one of her friends and (her sister to keep her out of trouble) to see a movie so it would work out well. I went home showered shave really close, shaved my legs Lori and I regularly go for couples Brazilian bikini waxes so I'm pretty much hairless and smooth just like she likes it and I love the look and the feeling as well. I slipped my cock into a gaff that Lori and her girlfriend had bought for me to wear when they had me dress fem for them something that has become a regular part of life around the ranch as we say. As I’m sure you’re aware a gaff is a special panty type device so to speak where you slip your cock into a sheath and its pulled up between your legs affixing to the back of the waistband so with your cock tucked between your legs it gives your front a much more anatomically female appearance this one of several but I choose it because it has a vagina what the girls also liked it prevents me from getting a hard on a sure giveaway for any guy trying to pass as a woman I then proceeded to get dressed as Brandy my feminine self.
I put on a pair of red and black lace trimmed satin bikini panties with a matching bra and had to decide if I was going to wear a garter belt and stocking or pantyhose or thigh high hose decisions, decisions so thinking the patent leather mini skirt I had in mind it would be much better choice to go with a pair of black thigh highs. I chose a black satin blouse that Lori had bought for me during one of her shopping sprees topped off with a black leather jacket.
(Since accepting my long-dormant crossdressing due in part to her new found bi-sexuality she was all in and really immersed herself into encouraging me so what better way but to buy me clothes, clothes that made me look slutty just the way she wanted me to look when I was her bitch but tonight I was going to be Dave’s bitch. She did tell me she had plans to buy me a few tamer outfits for around the house but somehow, she hadn't gotten around to it hmm I wonder why)
I left my blouse unbuttoned just enough to see a glimpse of my bra although the silicone breast forms that were not just a pair of falsies stuffed into the cups of my bra but rather they are high quality that actually glue to the chest so they would stay in place even if I were to go topless they appeared to give me nice full breast. I longed for pair of real tits with ample cleavage and nice perky nipples forever I truly felt I was a woman trapped in a man’s body and deserved to be feminine but Lori drew the line at any sort of implants or anything hinting of female hormones therapy etc., she reminded me that I had a very successful business that I busted my ass for and going to that extreme was just too much which of course she was right hence the reason she did so much research and spent the money on these, which I had several different sizes and shapes variants but tonight for Dave I was a 36D I wanted the extra slutty look. I did my makeup and donned one of the wigs Lori purchased for me I don’t possess the famine skills with a hairbrush and blow-dryer to do my own hair that something the girls do, tonight I was going to be a redheaded slut. There was no doubt in my mind what Dave wanted when he asked me to dress up and after having one hell of a great time the night before I was more than ok with it, actually thought about him fucking me the entire following day even while having sex with Lori I was dreaming of Dave’s big cock and the ass pounding and mouth fucking I was given so I figured I may as well look the part.
I finished my outfit off with a pair of thigh high patent leather boots with platform heels so I could walk without breaking my neck I hadn’t yet mastered pumps or spiked heels but was working on. I owe all what I know about dressing slutty to my wife who outwardly is a very conservative house wife that is until she decides to let her hair down and have fun, even her co-workers said she like has a Jeckle & Hyde personality there is work and Lori who is all business and then there if fun Lori who is a party animal who likes pushing the limits.
I made sure to pack my guy cloths and a few essentials in a gym bag just in case, I am a very passable crossdresser plus going out at night eases fears of being outted. I’ve driven around a few times alone and more than a few with Lori and her live in girlfriend something I used to do with my ex a lot. One night we pulled up to a light and I saw these two guys eyeing us from across the street when we stopped at a light and as it happened I knew one of them, I told Lori and she got all nervous saying what do you want me to do, I said do nothing don’t even look just wait for the light to change and go. She did as instructed and made a few turns here and there looking in the rearview mirror ok I don’t think anyone is following us. I laughed and said I think you watch too many cop shows on TV.
So, I strut my ass through the house checking myself out in one of the full length mirror saying to myself hey I’d fuck you. I made my way through the kitchen and into the garage and throw my bag in my triple black Cadillac CTSV with tinted windows of course...lol I fire the beast up and hit the garage door remote and I’m off for a great night of fun with Mr. Big, I plug the directions to Dave’s place into my GPS about halfway there I decided let me fill up. I pull in and we don’t have self-service where we live, so I wait for the attendant who is checking out my ride to come over and I lower the window asking him to fill it up in my best female voice which isn’t the greatest so I know to keep my words short n to the point. Wow lady you have a really nice car, oh shit it’s got a 6 speed, how fast will it go? Ok so Barney is very chatty, and I don’t feel like giving myself away, so I place my hand up to my throat and whisper sore throat. Oh, ok I’m sorry I just smile thinking don’t you worry I’ll be getting something for my sore throat real soon Dr. Dave’s two ball compound. He finishes up and hands me my receipt and my card saying ok I hope you feel better, I just smiled and blow him a kiss and headed on my way to Dave’s
I pulled into the driveway of a very modest home in what appeared to be a quite middle class neighborhood. I strutted up the walkway in full view of some couple walking their dog who I knew was checking out my ass how could he not. I rang the doorbell and the door opened and there was Dave wearing a cut off sleeveless shirt and a pair of jeans his jaw almost hit the floor as he stood there for a second with his mouth open and finally said holy fuck your even hotter in person. I smiled saying so you’re not a breast man but how do you like mind, with the front door still open he leaned in and planted a kiss on my lips and slipped me some tongue, without stopping he reached for my girls with both hands groping and fondling them God they even feel real. Ah Dave still fondling my tits unless you want to put on a show for your neighbors, oh yeah and he reached for the door with one hand and flings it shut. He whisked me inside and continued to feel me up when before I knew it he stuck his tongue in my mouth and firmly held my arms at my side now I am not a small or weak person but Dave is massive pro-football player size so that combined with the overwhelming feeling of lust I was paralyzed and he knew it, when he broke off the kiss he just smiled saying I knew you wanted that since that night. Maybe he was right or maybe I was just taken by surprise and filled with the lustful thoughts of his big cock inside me since he called. I was breathing heavily and just looked at him returning his kiss we now played tonsil hockey for a few minutes as fondled my tits and grabbed my ass. He firmly grabbed both ass cheeks saying now that’s some ass and I know it’s real. Oh yes, it is but you ought to know that as you violated it smiling at him, we both laughed violated it I said yes it sounds a little more lady like that you fucked me up the ass, so I was walking bowlegged the next day. Oh yeah by the way weren’t you taking me out on a date, oh yeah he laughed how about a couple of drinks here first ok well I could use a good stiff one, glancing at his crotch which was showing the outline of his ample member, he said well if you insist laughing let me get you a drink first. Good idea I replied he returned with a couple of beers and a two shot glasses and a bottle of Tequila. We sat on the couch and did a few shots and had several beers while he asked me a bunch of questions about my crossdressing the how long the whys, etc. and how did I get Lori so into it. Well that was a lot easier than I thought to be honest she has to be one of the kinkiest women I have ever met so to her it was just another way of enjoying kinky sex, I guess plus she is the love of my life and I will do pretty much anything in the world to please her. Hey not for nothing I really don’t mind the questions but talking about my wife right now isn’t doing anything for the mood if you know what I mean. He agreed and we made small talk about this and that and next thing I know is his hand is on my knee and he leans in to kiss me, I willingly accepted his kiss which turned it to more and more, throwing all my resistance and lady like decorum right out the window(lady like my ass I am a true slut no doubt about it. Then our heavy petting session ensued as I felt his hand going further and further up my inner thigh, so I reached for his massive member still hidden in the confines of his jeans and started rubbing it. I knew it had a positive effect on him as he started to squirm a little. His hand kept moving up my thigh till he reached where he expected to find my cock. He started feeling and reaching in my panties and I playfully slapped his hand down sailor I laughed. He picked my skirt up and peeked under saying what the hell. Well DavieI just said I wanted to dress for the occasion figuring I wasn’t going to be the one doing any penetrating but rather the one being penetrated you mean you’re the one who is going to get fucked, I said yes sir now that’s the whole purpose of me being here isn’t it. He laughed and said well I did invite you for a couple of drinks now didn’t I. I laughed and figured it was time for me to go into my slutty prostitute persona one of Lori and Barbies favorites when we role play.
So, you want my ass do you now well it’s going to cost you honey, Dave played right along, oh really now so how much is this going to cost me he asked. I said well depending on what you’re looking, everything baby I want it all he laughed, ok all it is then, for everything plus the house call fee I’d normally get $500 for the night he raised his eyebrows, but seeing as you know Lori you get a special discount and I’ll let you run a tab. He smiled and said well I hear your worth every penny and kissed me I said do we have a deal, he squeezed my tits and said yes baby we have a deal. Ok first let me go freshen up a bit and I got up and excused myself to go use the bathroom. I did have to pee and now I know fully what women have to go through every time nature calls. So, I finished up my business but before I returned, I took a small bottle of lube from my purse and stuck it up my ass and squeezed it filling my anal cavity. I knew all too well what to expect from Dave’s massive cock and that the night before I was pre lubed and pre stretched from Lori’s pounding so I wasn’t taking any chances, I readjusted my gaff not yet owning the type that will allow you to pee without removing it, I pulled up my panties and adjusted myself and pulled out a tube of lipstick from my purse the girls had thoroughly schooled me in the art of applying makeup as they put it they wanted the me to experience the whole package the entire female experience not just putting on a bra and panties. I applied my lipstick and put the tube back in the purse along with my tube of Astroglide our favorite and headed back to my date.
Now not being totally naïve in the ways of dating etc. not wanting to be the victim of a ruffe not that Dave would do that but you never know so nit until I knew that I could trust him 100% was I going to take any chances I grabbed a couple of fresh beers from the frig took a nice big swig and picked up the bottle of Tequila and took a very liberal hit and passed the bottle off to him. I asked Dave if he had any weed but he said no he didn’t but could see if he could score some from his friend, that would be great if you could although I was relaxed but that little something extra would be just what I needed, so he sent his friend a text then he said well it’s time to get what I paid for and he went to unzip his jeans.
I took his hand saying allow me. I dropped to my knees and slowly unzipped his tight fitting jean reaching in for his cock I gently removed it and it practically sprung to life. It seemed bigger than I recalled maybe in part to like I said earlier my lustful desire I began kissing the head of his dick and running my tongue all over the head which was now adorned with the baby pink lipstick I was wearing, one of the things Lori loves to do to me, I was mimicking so many of the things she does and has taught me. Hell, I was taking on her persona. I kept licking him and kissing the head of his cock teasing him so as to make him even harder, I than say on his lap facing him and grinding on his massive cock teasing the hell out of him oh didn’t I tell you a lap dance is part of the package all he could do was smile saying your such a fucking cock teaser. Oh, you have no idea honey as I gyrated on his throbbing member, I could feel it like a big snake was coming out of its hole, yeah looking for mine. I then turned around, so I was facing away from him but lowered myself back onto his cock and continued by bump n grind knowing it was driving him nuts. I then thought ok I’ve teased you enough time to get down to business. I got back down on my knees spreading his legs apart and proceeded to devour his cock, I sucked and slurped and got it slick and glistening from my saliva. I sucked the head of his dick and flicked it with my tongue.
He was moaning and groaning holy shit you give the best head, looking up at him saying oh better than your boyfriend, he laughed and said that bitch can’t hold a candle to you slut.
Oh by the way where is he, I asked. I told him to go back to his mother because he bitched so much ok so he’s not going to come back and get his panties in a bunch, nope not a chance it’s just you and me baby. Good as I engulfed his now rapidly hardening member. As I sucked, I unbuckled his belt and undid the snap on his jeans and teasingly pulled down the zipper. I then grabbed the waistband of his long leg briefs and pulled them and his pants all the way down to his ankles. Now his cock was clear of obstructions and free for me to suck and to lick his balls. I was pumping his shaft as my hand as my head bobbed up and down on his hard cock, I could feel it hit the back of my throat and knew I was going to try to deepthroat him but by his shear length and girth is was not going to be an easy task but I was willing to give it all I had.
So as I continued to slide his cock in and out of my mouth each time I kept going deeper and deeper, taking more of it in each time I did gag somewhat but was not about to give up as long as he wasn’t forcing me I knew I would be ok because I could stop anytime I wanted. Now I had it planned that I would give Dave the best blowjob possible and then give up my ass all things going as I planned in my head on the ride over to is place as the night continued. Dave was moaning saying oh yeah bay that feels so fucking good has anyone ever told you that you suck a mean dick. Ah hmm was my response as I didn’t want to interrupt my pursuit of getting him into my throat. I kept sucking and slurping massaging his balls and stroking his shaft but I for one enjoy a true blowjob no hands are involved it’s all about oral skills. I never appreciated a woman jerking me off into her moth not that it’s a bad thing, but a blowjob involved sucking and stroking is to be done with the mouth and lips. As hard as I tried, I was unable to fit the entire length of his shaft far enough in to reach my throat, but Dave didn’t seem to mind. His breathing was now increasing and his hips starting bucking and I knew he was getting ready to blow his load and I was determined to swallow every single ounce. As his pace quickened and so did his breathing, I increased my speed and sucked him harder and harder until he let out a long loud moan of fuck! Fuck! I’m cumming you slut whore suck my cock bitch. He no sooner got the word bitch out when he began shooting hot ropes of cum in my mouth and I feverishly sucked his cock, as he pumped load after load of hot jizz I suck and swallowed almost every ounce of his cum.
Dave exhaled and relaxed his body, but I continued to suck his cock clean which by now was extra sensitive so much so he almost couldn’t stand it. I had plenty of cum left in my mouth, so I got to my feet and planted a deep French kiss on his lips spitting his cum into his mouth. This took Dave totally by surprise and he attempted to pull away, but I had a firm grip on his head which made him realize any resistance was futile. We kissed for a minute and finally relaxing my grip I pulled away and took a step back and just smiled. So, tell me who gave the better blowjob me or Lori I laughed. His response was holy shit now talk about putting a guy on the spot like I said I am really not into women but man your wife gives one hell of a blowjob. I said yes, she sure does and like she said she taught me everything I know. He laughed saying remind me to thank her. Oh speaking of Lori does she know you’re here he asked, no I said she has no idea she went out for the evening and knowing her she won’t be back till late she’s not out catting around not because she wouldn’t but she’s with her sister and their friend her sister has no idea of her wild side so she will have a pretty boring evening. Ok it’s our secrete then that’s fine, I said oh Dave he looked at me as if to say what you may want to consider taking her up on her offer to fuck her. He looked at me as to say what the fuck. I said listen I’m perfectly fine with you doing her and she does have a hall pass that she has never used but I know her, and I know she wants your cock and will be relentless and not stop until you fuck her brains out ok, I’ll think about it. We both sat on the couch Dave bringing us each a cold one, now he was totally naked he sits down next to me telling me how wild I am I said hey, look who I’m married to and we both laughed. I said ok here is one rule I have you can fuck me in the ass all you want cumming in there is fine too but don’t expect me to put your cock in my mouth after its been in my ass, if you want that you need to wear a condom. He looked at me saying I don’t have any, I reached for my purse on the coffee table pulling out a strip of at least 6 magnum condoms I said a girl has to be prepared especially us working girls.
We both laughed and I grabbed his cock and started playing with it, I stood up saying let me take off my jacket at least, so I stood up and removed it and tossed it on one of the chairs, while I was up I unbuttoned one button of my blouse revealing my bra and not to mention my cleavage Dave was amazed looking at me saying you have real tits as he squeezed one I said not exactly just modern technology a little body makeup and good strong glue, I opened my blouse all the way and said look I even have nipples popping one tit out of its cup. He just looked them over and said amazing. Wow I never would have thought you guys were so into it.
I laughed saying you have no idea we fool everyone. I then said fuck it and removed my blouse and tossed it on a chair now only wearing my bra and skirt and stockings still wearing my boots though. The entire time I was playing with is dick and talking about my tits he even asked if I could fuck with my fake vagina that I said has yet to be tried but I think you’re a wee bit too large for that. As he talked about how kinky we were I could feel his cock beginning to pulse, so I smiled and said well back to business the meters running you know and proceeded to go down on his beautiful piece of man meat putting it in my mouth getting right down to business. It didn’t take very long before Dave was fully erect and ready to get down to business. He stood up and hand me bend over asking me if I was ready. It’s all yours honey. Dave stood behind me slipping my panties to one side and guided his big fat 10 plus inch cock into my pre-lubed ass. His length was not more than I had grown used to over time with Lori using rubber dildos on me, but his girth was incredible he was a big around as a beer can I’m guessing, I was really glad I had thought of the idea. He moaned as she slowly slipped it in inch by inch until he was buried balls deep inside me. He began slowly fucking me in and out pulling it almost the entire length out with the head stretching my sphincter to its limit as he would slide it back in every time he did this I let out a moan and tried my best to control my breathing and relax my body enough to take the fucking Dave was giving me. He continued his slow rhythmic pace and I now met his thrust with my hips pushing back towards him, it didn’t take long before we were in perfect sync, The feeling of him filling me sliding it in and out was beyond euphoric, He reached around and cupped both of my tits as he slammed his balls into my ass cheeks remember what I told them about being glued in place but not to get too carried away, truth be told they are not that easy to remove it does take a little doing so I wasn’t worried about them falling off or popping out onto the floor like by other implants the girls had gotten, yes I said implants Barbie my wife’s girlfriend works in the pharmaceutical industry but has connections with several plastic surgeons all of whom want to fuck her badly but that was something that was never going to happen her pussy belonged to my wife so she scored me actual saline implants they use in breast enhancement but these were far more realistic in all respects and made me feel like a woman, the woman I was meant to be I was getting lost in Dave pounding me, he had both of my tits and popped them out of my bra they were swinging and swaying with every pounding of my ass, this went on for a few minutes I caught my breath saying stop, stop let me put them back in it feels better not the same dilemma as my wife with her all natural 38DD melons having some heft to them but even mine had enough that I could feel the pulling sensation. I no sooner popped them back in Dave continued his pounding of my ass, my long red hair wildly flying about my tits swinging within the confines of my bra being tested to the limit. I was so deep in the trance of my ass being pounded and most of the time I had my eyes closed and would open them when Dave would slap me on my ass first on my skirt covered ass then he had my skirt lifted enough to bare my entire panty covered behind. I hear Dave mutter something and I open my eyes looking right at this guy gawking at me getting fucked silly by Dave. It turned out to be his buddy Richie his weed connections. Well either Dave didn’t lock the door, or he had a key but regardless of how he was now standing with in an arm’s reach of me. I was shocked to say the least but in no position to do anything about it being as Dave had me bent over so far, I couldn’t have straightened up and pulled away even if I tried or was it if I wanted to?
Well Dave never broke stride and kept pounding me in the ass. His friend said hey sorry man I didn’t hey since when are you into chicks. Dave said since I met this bitch, laughing he said this is Bobby stopping short of saying you know Lori’s old man as I was to find out later, he had met my wife once or twice. Oh, wow and the next thing I now is this guy has his cock out Dave says do you mind, I had to say no I’m not ready for this, again I said no! and stopped my hips from meeting Dave’s thrust so he knew I meant business and not wanting to ruin a good thing he said sorry man you gotta go. Having two cocks is probably every cock suckers dream but I wasn’t lying I just was not ready for it, maybe because I was taken by surprise. His friend didn’t hurry up to leave and continued to gawk as I was still getting pounded, finally Dave said you really gotta go dude, and his friend took the hint and left Dave called lock the fucking door asshole. Dave slapped me hard on the ass several times and said now where we he was now pounding my ass hard I could hear his balls slapping against my ass and I got back into the rhythm of us fucking Dave had now been in my ass for a good 20 minutes total and I was really hoping he was getting ready to cum because I was getting really sore. I asked him if he wanted to cum on my face or on my tits figuring jerking him off would be a lot less uncomfortable. No baby I’m getting ready and he started shuttering almost as if his body was convulsing, he started grunting oh fuck! oh fuck yeah baby I’m going to fill your ass with that I felt like a firehouse of hot loads of his cum begin to fill my ass. I stopped my meeting his thrust, but Dave still kept pounding my feverishly I could not only feel my ass squishing but could hear it as well as with every thrust I could hear the sound of his cum which was now overflowing my asshole I was filled beyond capacity. Dave gave me one last mega thrust getting his last once of cum into my ass almost knocking me over onto the floor. He stopped and was breathing heavy holding on to both of my hips he was not about to move until he caught his breath, he said later he needed to hold on to me or he would have fallen flat on his face. I told him I have to get up and it one swift motion Dave pulled his massive cock from my ass not only did it pop from the hydraulic seal of my ass being over filled with his cum, but the size of his giant head leaving my hole wasn’t exactly pleasant feeling it was akin to a hot poker being stuck in my ass, how I didn’t pass out is beyond me. We both collapsed on his couch my ass leaking cum. I told him to go get me a towel at first, he didn’t move right away but I said towel now. I stood up and there was a large cum stain on the couch cushion oh well I thought as I used the towel to clean myself. I said he you made the mess you ought to be the one helping me clean up. He laughed and said gimmie holding out his hand I stood up and he proceeded to clean his cum from me with the towel when all of a sudden, I felt his hands on my hips and his tongue licking my ass. I was thinking ok this isn’t so bad, kind of makes up for shithead not locking the front door. I sat back down fully intending to go at least one maybe two more rounds with Dave when he gets a text fucking asshole he muttered. I looked at him what, my asshole friend couldn’t keep his mouth shut I should have known. Within seconds he get three more texts wanting to know if his date was still there, hey are we having a gangbang he is apologizing to me like no one’s business. I stood up he said please don’t go. I just said I’m outta here I’m not getting gang raped by your friends and forget about fucking my wife your friend ruined a good thing. My plan was to get changed into my regular cloths for the ride home but, no time for that I gather up my stuff fixed my bra and put my blouse back on ran my fingers through my hair thinking it’s time to get the hell out of here before I am the party favor for a bunch of his friends. I said see you around Dave and remember what I said all he could do was sit there with his big now flaccid cock saying he was sorry, well we did have a lot of fun yeah but I planned on having a hell of a lot more fun but your friend fucked it up I said and left I got in my car and headed off not even turning on my lights for a block or two.
I had thought about stopping somewhere to change but decided against it, looking at the clock I figured I still had plenty of time before Lori got home. Well wrong I was not only was she home, but her sisters car was in the driveway, I grabbed my phone and sent her a text is everyone still awake/ She responded yes, we’re having a glass of wine why are you home, I said unlock the French doors in out bedroom. Of course, I get why just come in through the garage I text back French doors unlock now! no need to explain. She excuses herself to go use the bathroom and instead of using the one right off the kitchen she goes into the master bedroom she unlocks the French doors and there I am standing there looking like the whore that I am, thigh high boots mini skirt big tits pushing against my blouse. She laughed and gasped covering her mouth so her sister and their friend would hear her Holy shit what the hell, where you out turning tricks no not exactly let me get out of these clothes and I’ll explain later. She laughed and said oh no you don’t you’re going to stay right here dressed just like you are oh and by the way you look fucking hot and then you’re going to tell me all about it and I am going to fuck your brains out do you understand, reaching in her dresser draw pulling out one of her strap-on’s. Yes, yes who she glared I said yes mistress but what about your siter and your friend oh they are ready to pass out they’ll sleep in the spare room so you sit your pretty little self-right here on the bed and wait for me do you understand looking up at her yes mistress was all I said as she walked out the door back to the kitchen. I waited seated on the bed like a good little sub slave but the entire time I was thinking about the great fucking I had gotten from Dave, maybe I shouldn’t have freaked out, maybe I should have sucked his friends cock, hell most go a life time without ever having a threesome and I literally had it right with in my reach Dammit what a fucking idiot I was. I even could have stuck around to be gang banged by Dave and his friends my head was spinning with all the possible scenario’s. I picked up my phone and sent Dave a text. I’m still pissed but I forgive you lets hook up in a couple of day give my ass a chance to recover. All I got back was the smiley face
