We both enjoyed my playing the role of her shemale girlfriend so much that we continued for months it was almost a given that after work no matter whose house we were at I would be dressing fem. She surprised me one night with a purple see thru bra top nightie with matching sheer panties. I was a bit giddy and got up off the couch and said let me go try it on, as I got up, she slapped my ass pretty dam hard and said bring me a drink when you come back will you honey and don’t forget your titties.
She surprised me a very realistic pair of silicone breast forms along much more real looking than my collection of real silicone implants that I would stuff in my bra which added a nice giggle to my tits when I moved, she would actually glue breast forms to my now hairless chest and with a little touch of body make up they appeared to be 100% natural. She told me if she didn’t have connections these would be super expensive when I asked how much she smiled and said don’t ask baby your worth it I replied yes dear.
I returned shortly with a cocktail in my hand and sat it down on the end table next to the couch. I said well how do I look? She had me do the rotation so she could get the full view while sipping her drink. And said very sexy I like it a lot. She motioned for me to come closer which I did when I was face to face or shall I say crotch to face she lifted my nightie and sucked the head of my flaccid penis through my panties, the feeling was one of euphoria I placed my hand on her head and began softly stroking her long brown hair. She continued to suck my panty covered cock until It started to grow, she then held my hips and had me turn around. She commanded me to bend over, I did as she requested, and she grabbed my hips and pulled my panties down and started rimming my asshole. She knew that this was one of my weaknesses, the next thing I knew she was shoving a finger up my ass and began finger fucking me. I was loving it and she would reach around and grab my cock and stroke it and pull on it like she was trying to milk my cock for its cum. She asked in a sultry voice you like me fingering you baby, I moaned out oh yeah I do, without warning after she pulled out she inserted two fingers, this took me a little by surprise and I must have winced a little so she told me to just relax and let it happen.
I did as she asked took a deep breath and did my best to relax and she slowly inserted the two fingers and slowly fucked my asshole a little increased speed and fever. She started asking if her little bitch liked getting her ass fucked. I said oh yes baby I love getting fucked in the ass by you. She said good, unknowingly she had taken out a vibrator out of her big oversized bag and squeezed a little bit of gel on the tip and shoved it in my ass. I thought I was going to shoot across the room. She slapped my ass and saying relax! I’m not going to hurt you just breath. Again, I listened and relaxed which made it much easier to bare, I don’t want to mean that as being a bad thing, it’s just following her directions made it more enjoyable and I loved her assertiveness. After a few minutes of vibe fucking me she said bend over the ottoman and rest on your forearms. I did and she pulled my nightie up and told me to stay right there. She excused herself and went into the bathroom. I suspected she had needed to go tinkle as she always would.
Within a few minutes I heard the door opened and I could hear her walking across the living room floor. She walked up behind me and slapped my ass more than a few times, her slaps where firm and forceful this is something, to love doing to me because of how much it turned me on, with every slap it stung but it seemed that with every slap my cock grew. I so loved getting a spanking from a woman it brought out my submissive side but especially from her. I was thoroughly enjoying my spanking when she stopped the next thing, I know is I feel one hand on my ass cheek and I then felt something being inserted into my asshole. I stood up and placed my hands on the ottoman and turned to see her wearing a black strap on harness. She smiled her devilish smile at me and said you need to be really fucked and with her free hand she began guiding the 8”rubber dildo of her strap on into me. My natural reaction took over and I tensed up next thing I know is she slaps me hard on the ass and sternly saying relax! With that she proceeds to slip the rubber cock into my ass until the balls of it slapped against my ass. She then grabbed my hips with both hands firmly and began fucking my ass, slapping my ass at times saying you like taking it up the ass don’t you, you little whore. I was panting saying oh yes! Yes! Fuck me baby, you own me now. She loved my response. You’re fucking right I own you but seeing as how you like cock so much maybe we’ll find you a big black cock to fuck your tight little asshole. In my mind I was thinking oh fuck some big black bull is going to split me wide open. As enticing as it may have been, I was nowhere near able to take on such a challenge. She continued fucking me and suddenly, she starts to shake and saying oh fuck I’m cumming and is pounding my ass with the intensity of a jackhammer. She stops thrusting and I can feel her body shaking. I was to find out later that her strap on had a small clit vibrator on the inside as well as a dildo inserted into her pussy.
Her orgasm finally subsided, and she withdrew her rubber cock from my ass, she told me to get on my knees I was faced to face with her big cock, she peeled off the condom and threw it aside. She placed her hand on my head and said blow me bitch! As she shoved the head of her cock in my face yelling open your mouth you bitch, I want you to suck my cock now. A few of the same phrases I’ve used on her during rough sex. I opened my mouth and grabbed the shaft of her cock with one hand as I guided it in. My initial reaction was as expected I gagged on it. She had the presence of mind not to force it in my mouth or things surely wouldn’t have not gone well. I now mustered up all the cock sucking experiences I had in my life drawing on the experience of how many women’s mouth my cock has been in. I sucked on it as I bobbed my head in and out taking it a little deeper each time. She now had her hand on the top of my head softly stroking my hair, that’s a good girl suck my cock baby. Do you like when I feed you my cock. I simply nodded as best I could and muttered ah hmm in approval. She pulled it out of my mouth and slapped me across the face several times and said say it bitch, let me hear how much you love sucking my dick. On my knees subserviently I said Oh yes, I love your cock I love to suck you off please cum in my mouth for me please. She let out a soft moan oh that my good little whore. I went back to my blowjob and got into a rhythm of sucking and breathing and occasionally I would lick the head and entire length of the shaft I decided to kick it up a bit as I slipped a finger into her pussy and fingered fucked her finding her G-spot as I rubbed it she began a series of soft moans I could tell she hit the switch for the pussy vibrator as I could feel the vibrations in my mouth.
I glanced up and she had her hand on her clit working at getting herself off. Within a short time, she began to moan and her hips bucks to meet my sucking and she was actually fucking my mouth. I swear if it was a real cock, she was about to blow her load. She finally thrust her hips one last time and let out a moan, one could only assume by the all too familiar sound that she had gotten herself off.
When she was finished, she told me to lay back on the bed and observe, she picked up a small remote and turned on the video camera she had set up to record our fuck session, this was nothing new as we often enjoyed watching ourselves as if we were in a porn video, as she went to town sucking my now rock hard cock. She would stop occasionally and give me a brief explanation of what she was doing and why. You’ll see it will all come to you in due time. In the heat of her sucking my cock, she complimented me on doing a nice job then asked do you think you’d ever want to try the real thing. I was shocked and titillated at the same time, role play was one thing, but my girlfriend wanted me to suck dick. She continued her fantastic head giving skills until I shot my entire load in her mouth bucking my hips trying to get every drop of spunk down her throat. One thing DD loved was cum, I liked shooting it on her tits once in a while, but she thought it was such a waste.
She crawled up next to me in bed and kissed me on the mouth and shared her prize with me, something we’ve done many times but never after her asking me if I was interested in sucking dick. She was speaking to me in a soft sultry tone and asked so you never answered my question. I confessed that I did have a curiosity about doing it but never gave it much thought. She then said well if you feel like giving it a try, I can set something up with one of my friends. My immediate thought was she wants to cuckold me and have some guy fuck her brains out and have me suck his cock. I simply said oh do tell and what else is your friend going to want to do, she didn’t need to be a detective to know that I was a wee bit jealous and had no interest in seeing her get hammered by another guy, she laughed and said don’t worry I have friends with cocks who have no interest in me.
We continued or role play, always with over the top wild sex I couldn’t have asked for anything more well I was going to get more weather I liked it or not. The next day and early evening was a repeat of our typical weekend activities me playing my role of her shemale boy/girlfriend, but she had more in store. She decided we were going out cruising in her convertible that night and have a few a few drinks, our first or shall I say my first outing as a woman went much better than I ever expected it would so my comfort and confidence levels were high but going out at night was like an added level of security if you will. She had me put on a pair of her black stirrup pants and a pair of ankle high black boots, and one of her black lycra body suits, she applied my new lifelike breast forms with some adhesive whihc kept them in place so no wardrobe malfunctions and applied some body makeup to finish off her handiwork I slipped them into a black satin bra and had slipped my cock into the black satin gaff, the sole purpose of which was to hide my bulge and keep my cock from getting an erection and retain a smooth front like the women I was supposed to be she stepped back and took a look and, she tied my black button down blouse at the waist, my attire to say the least was not masculine at all, she even went as far as styling my hair longer but not quite shoulder length feminine looking which didn’t look that bad but she assisted me with my makeup and I looked pretty good not overly sexy or trashy but just very feminine looking after checking myself out in the full length mirror I was pleasantly pleased.
We hopped into her car and cruised around for a while it seemed when we stopped at traffic lights, we always garnered some attention, we took a ride out to one of the Truck Stops off the interstate we slowly cruised through the parking lot the entire time she was teasing me saying so wanna make an extra $50 and give a blowjob. I just looked at her saying I don’t think I’m ready yet. She said that’s ok but when you’re ready I really think it would be hot to see you suck a guy’s dick. I asked oh really, why, she said I just find it hot watching guys sucking cock, it would be extra hot if it was my boyfriend. I asked her so you’ve asked this of guys you’ve dated. She said yes but sadly no takers you’d be my first. Now for some reason that had a strange appeal that I would be the first guy to fulfil a fantasy of hers. She drove a little more and turned into a gravel parking lot saying let’s go have a drink I’m buying. I looked at her with the shocked deer in the headlights look, she laughed saying its ok you’ll be amongst friends here it’s a gay club. As if she flipped some kind of switch I was instantly more than ok with the way I looked and excited to go inside.
Holding hands as we went inside the dimly lit club with blaring music fucking disco or club dance music or some shit I’d never listen to, DD seemed to be at home. She told me these are some of my people and they are all cool, not cool isn’t tolerated here. We weren’t inside two minutes when this musclebound dyke dressed in a leather corset, black chaps, with short bleach blonde hair wearing a spike choker collar came up to DD and gave her a big kiss and not on the cheek hugging her and asking how she was its been a long time, she looked me up and down and not exactly sure what she thought of me by the pause that seemed to last forever she asked so is this your new toy? DD laughed and said no this is my boyfriend Bobby; he is indulging me tonight. Spike I’ll call her reached out her hand and said nice to meet you Bobby welcome to my club, watch this bitch she’s fucking crazy I laughed and said in a good sort of way. DD broke the ice by saying hey you two have something in common she looked at me and said Bobby has several Harley’s and knows everything about motorcycles. Spike was like no shit I ride a Sporty and we started talking bikes she asked me everything under the sun and I fired answers right back to her. She was thoroughly impressed, DD went off and got use a round of beers and shooters, when I asked what was the shot, she said don’t fucking worry about it just drink it. We had a few more rounds and I got more than a few looks from guys of course because women in this establishment had no interest in the men.
I had to excuse myself and asked Spike where the men’s room was, she laughed and said we don’t have one, the look on my face must have been priceless. DD said it’s a genderless restroom. Ok then so off I went to genderless land to pee. When I walked inside let’s just say the bar scene in Star Wars had nothing on this place. A guy was getting a blowjob in one of the stalls and some guy in a business suit who looked like an insurance salesman from Iowa was watching beating his meat. I stepped into one of the stalls pulled down my skin tight pants pulled down my gaff panty and straddled the bowl I was not sitting down in there no fucking way and let out a long steady stream of relief. I did my best to readjust my clothing while still in the stall. I exited the stall and walked over to the sink and washed my hands while doing so Mr. Insurance wanker was flailing his cock gawking at me, I was about ready to knock him out but remembered DD telling me everyone here was cool, so I just ignored him. Not everyone in here is a freak this good looking guy standing at the next sink said to me. I replied I guess not, he asked if it was my first time here and I told him yes. He asked if I was here alone, I said no I’m with my girlfriend. In there that could have meant anything or anyone, I guess. I dried my hands off and left, it took me a little while to make my way through the crowd to find DD.
While doing so I got my ass pinched and a hand cupped it for a nice healthy feel, remembering everyone in here is cool and I guess I should take it as a compliment. When I finally found her, it was apparent that her and Spike had a few more shooters while I was gone evident by all the empty shot glasses on the table. She laughed and said you’ve got some catching up to do baby leaning over giving me a big long tongue kiss saying you have no idea how happy you've made me tonight by coming here with me capped off by sticking her tounge in my mouth Then she said let’s dance and dragged me out to the dancefloor. I was keeping up with her the best I could but was no match for her I told her I’ll be right there pointing to the post by the dance floor. She nodded and continued to do her thing. I was standing there watching her and decided to step back a little off to the side and stood leaning on one of the tall tables.
The place was crowded, and you couldn’t help but contact another person so someone rubbing up against me wasn’t unusual. I was standing there and the next thing I know is I feel someone grinding up against my ass, I remained cool most likely do to the fact that I had consumed a large amount of alcohol, so I just went with it. I could feel an obvious bulge rubbing against my ass and seeing as I hadn’t resisted it must have been taken as a sign of approval, so the person continued. Subconsciously realizing what I was doing I leaned in such a way that my ass jutted out a bit more. My newfound admirer continued grinding his cock against my ass picking up the tempo as if to keep up with the beat of the blaring music and now there was no mistaking that I was getting dry humped right there in a crowded room full of people. I finally had to turn around to see who this was and when I did some strange guy who was with Mr. hot looking guy from the restroom just smiled at me. He reached out to me and led me to a dark corner of the room, Mr. Hot guy smiled and said it’s a little more private back here and his friend got behind me and had both hands on my hips and was pumping at my ass and not just a grind but a full on thrust. I still wasn’t protesting because I was getting more turned on by the second I allowed him to continue, and I must admit I was thoroughly enjoying the attention. I felt him tug at the waistline of my pants and attempted to pull them down. When I turned his cock was out in full view and fully erect. I was totally into it and loved anal play with my girlfriend but wasn’t going to allow this guy to ass fuck me in a club full of people. So, I took a step back put my hand out and pulled my pants back where they belonged and walked away. I found my way back to the table, where DD and her friend and a few others were partying. She asked me if I was ok and I said I was fine and had another drink and a shooter.
After maybe fifteen or twenty minutes passed, she came up to me and saying let’s get go home, I agreed and we said our good nights and left. We weren’t even out of the parking lot when I told her what had happened. She got extremely excited saying were you going to let him fuck you in the ass, I said no not in a room full of people, what about in private she asked, this is so fucking cool she said half in the bag as she was. I said I didn’t know, she asked what about a blowjob. I think possibly just to shut her up I said yeah if it was in private, I might have. She laughed a little saying wow this is so cool but hey not without me being there you little slut. I said ok you can watch no problem. We’re driving down this two lane road when the next thing I know she turns into the parking lot of this bar, I looked at her as if to say what are we doing here she smiled saying we’re going to find you a date. I just looked at her and she said don’t worry I used to come here with an old boyfriend years ago and its nothing but drunks. I was like ok nothing but drunks She said I’m going to go in and scope the place out and see if I can pick up some guy. I said that shouldn’t be a problem ah just one thing what happens when this guy realizes I’m a guy. She said I’ll keep him distracted and when it comes to getting a blowjob believe it or not, I think most guys don’t care they just want their cock sucked. So, she parked off in a dark corner and off she went in and true to her word she comes back maybe fifteen minutes later with this guy much younger than her who is stumbling so bad he can hardly walk. She must have gotten from him where he was parked, and I saw her walking him to his car. She motioned for me to come over, So I got out of the car and walked over to her and this guy. She introduced me as her sister and said please excuse her she has laryngitis so it’s hard for her to talk. He mumbled something
About your hot and he kept saying over and over to DD. She asked him if he wanted to party, my sister hasn’t had any cock in a very long time since her divorce would you mind terribly if she gives you a blow job. He blurted out hell no I’d be glad to help her out. This obvious bullshit line never would have worked on anyone other than some drunk, next thing I know is he is fumbling for his belt and DD says here let me help you but sit in your car first honey get comfortable. He sits in the passenger seat and she reclines it all the way back she then pulls his pants all the way down around his ankles and positions herself in such a way that his view of me is obstructed. I got down on my knees and I no sooner did I knew kneeling in a gravel parking lot was not a good idea. I yanked the floor may from under his feet threw it down on the ground and knelt on it. I took his limp cock from his underwear and proceeded to put it in my mouth. As soon as it touched my lips DD told me later that her face was beaming. I mustered up all my cock sucking skills that I had practiced on her and sucked and slurped at his lifeless cock. I figured let me get it all out and pulled his briefs down exposing his cock and balls. I went back to sucking him and licking it doing every trick in the book. He was enjoying himself obviously by the moans I was hearing. He said let me see her suck my cock I want to watch her. DD ran interference by jamming her tongue in his mouth telling me later all she could taste was beer, I continued sucking his cock and decided to let me stroke him hard, basically give him an handjob with his cock in my mouth. When DD decided to come up for air, he attempted to sit up to get a look at me, again DD thwarted his plans by popping open her blouse and shoving her big tits in his face. One of her weapons she used to get her what she wanted at work. He grabbed at them and sucked on them in a frenzy, he actually bit her tit he was so aggressive, she promptly slapped him in the face and said hey asshole no biting. I continued sucking and stroking and succeeded in getting this guy a little pass flaccid but no way hard enough to cum but I wasn’t giving up that easily I continued to suck his shaft my head bobbing up and down and I squeezed his balls and was pumping his shaft I finally got him fully hard but is seemed that as soon as I stop it deflated, dam it! I was so fucking close to giving my first real blowjob and this drunk wasn’t cumming through I looked up at her and shrugged my shoulders and whispered what am I doing wrong. She mouthed just give him a handjob. I did as she suggested and a handjob is something I know everything about and as hard as I tried no pun intended, I couldn’t get this guy’s cock hard. She finally said let me try I don’t know whether out of frustration of me not doing a good enough job or with this guy not being able to get it up.
She went down on him and furiously sucked his cock, stroking his shaft and squeezing it attempting to milk the cum from his balls but no luck. She stood up and just said fuck this guy isn’t going to get a hardon if I shoved a broomstick up his ass. She said let’s get the fuck out of here baby. We started to walk back to her car when he cried hey where are you going, come back here and finish sucking my bam, he fell back in the seat with his pants down around his ankles and his limp dick just lying there. She said sorry first guy had whiskey dick baby, I laughed and said no problem I’m sure you’ll help me find a working cock. She smiled and said you know it baby, now let’s go home and I’ll suck your cock, I replied only if you let me suck yours, she smiled and said deal. On our ride we shared a joint which was totally mellowing me out that combined with all I had consumed at the club I was feeling no pain home she had the look on her face, and I could tell her wheels were turning, she pulled over and sent someone a text message and we continued on our way. I asked what was that all about, she smiled and said you’ll see. When we pulled into her driveway there was a strange car parked out front and I should have been nervous but hey I just had a strange guys cock in my mouth and was feeling no pain. When we got out so did the occupant of the vehicle. As it turned out it was one of her guy friends from work, she smiled at me and kissed me and said this is Paul and he’s not drunk. My eyes must have widened in anticipation of what was instore he smiled and extended his hand and smiled hand in a very famine voice said my you look good enough to eat, I had to have blushed both from his compliment and the large amount of alcohol I had consumed. DD said well this is nice but let’s go in I don’t think the neighbors need a show. So, the three of us went inside. DD said why don’t you two get comfy while I fix us some drinks and she headed off. I sat next to Paul who was a complete gentlemen unlike the horndogs in the club.
We made small talk and he told me that DD told him we were at the club. I asked him if he went there and he said he had but it was a bit crowded and could get really crazy. I was relaxed was relaxed with Paul and told him what had happened to me and he gasped and said that’s just not cool. I said yeah, I know hey if I want to suck a guy’s cock or get fucked in the ass it will be on my terms. He laughed and said yeah, he felt the same way. I then told him what he already knew about DD picking up Mr. Whiskey Dick in the bar, he laughed and said things didn’t quite work out for you huh. I said no and I was this close, he smiled and said well I think I may be able to help you with that, and he stood up and unzipped his fly and pulled out a beautiful cock I didn’t ask but it had to be at least 8 inches. Yes, he was bold, and I was drunk but my girlfriend text him and let him know I was ready for some real cock and would he be willing to help. I was seated looking at this fine example of manhood right there in front of me but she was right I was finally ready hell I just had a cock in my mouth so I reached out and took his cock and began stroking it, he closed his eyes and said see how easy it is. I was stroking it and was so focused I didn’t realize my girlfriend was standing there watching us. She smiled saying I see you two have gotten acquainted I looked at her and smiled and never said a word and just kept stroking his cock. He said let me sit sweetie. I liked that he called me sweetie and complimented on how nicely I was dressed and how feminine I looked. He said that from his perspective in parking spot when I got out of the car, he had no idea I was a guy. That boosted my confidence 1000%. I continued stroking his cock until my instincts told me it was time, so I started to pull his pants down he kicked off his shoes and his pants followed he helped me remove his bright pink panties.
I had to compliment him on how cute they were, and I had several pair almost like them. The small talk was over, and I proceed to go down on his cock stroking and sucking his member and unlike the cock from approximately and hour ago it almost instantly reacted to my sucking. I could feel him getting harder and harder and before long I could taste his precum. I licked the head of his cock clean and licked up and down his rock hard shaft, the entire time he was moaning and saying oh my your good, are you sure you haven’t sucked a lot of dicks because honey you’re really that good. I looked up at him and smiled and said no and DD chimed in and said I’ve taught him well. Paul responded oh you sure have. With that I went back down on his cock and continued sucking him and stroking his cock. Out of the corner of my eye I saw DD and I positioned myself so I could get a better view and could see she was fingering herself with one hand and cupped one of her tits she had removed from her bra and was pinching her nipple. She saw me and got down on her knees next to me giving me words of encouragement. That’s is baby suck his cock, this is so fucking hot I’m soaking wet and so fucking horny you’re going to have to fuck my brains out!
Come on baby make him cum I want to see you make him cum suck his dick baby you know you want his hot load. There was no question I going to make Paul cum, and I was laser focused on doing just that. I stopped stroking his cock and went on full suck mode. I love any blowjob, but a really good blowjob is when your cock is sucked clean by mouth only not a handjob with a dick in someone’s mouth. I figure I’m a guy and this is how I like it so other guys like it that way too. I was now bobbing up and down on Paul’s cock and had increased my speed and intensity of my sucking exactly as my girlfriend does when she is intent on making me finally cum. Paul was moaning and saying oh God oh my God I’m going to cum sweetie I’m going to cum and without skipping a beat DD was like a cheerleader at sporting event come on baby suck him off make him cum she yelled!
Paul’s body began to shudder and shake, and he let out a load moan and released a load of hot steaming cum from the head of his cock. DD knew the signs and said suck him baby swallow his load like I taught you. I did my best to swallow his load but a little escaped my mouth and was dribbling down my chin and was on my lips. DD swooped in and kissed me intently licking the cum from my lips and chin. She kept kissing me and saying oh my God thank you , thank you for doing this for me baby I love you. I smiled at her and said I love you too, she laughed and said now eat my pussy and fuck me I need it bad. I looked up at Paul who was spent from my cock sucking my cock was now hard as a rock and I needed some relief looking at Dee pointing to the other couch Still fully dressed fem I proceeded to just pull down my pants and slip my cock into her super wet pussy. I was pounding her pussy for all I was worth when Paul said I normally I’m not one for this, but you guys are fucking hot you’re a couple of animals. I pumped DD’s pussy like a jackhammer and after maybe 15 minutes I filled her pussy full of cum and pulled out of her and went down on her lapping my own cum from her pussy something I do most of the time while doing so I brought her to a screaming orgasam I looked at Paul and looking at her for approval and just asked if he would like to join me, he thanked me for the offer but said he was good with just watching the two of us. DD later on that night told me she couldn’t believe that me Mr. jealous had asked another man if he wanted to lick his girlfriend’s pussy, she laughed and said she wasn’t mad just surprised. The three of us sat on the couch, I kissed her neck and whispered would you mind, I didn’t even half to finish my sentence when she asked Paul would if he would mind fucking my boyfriend in the ass. My little slut is hungry for some man cock what do you say she asked. He laughed and smiled and said who am I to disappoint a lady.
She surprised me a very realistic pair of silicone breast forms along much more real looking than my collection of real silicone implants that I would stuff in my bra which added a nice giggle to my tits when I moved, she would actually glue breast forms to my now hairless chest and with a little touch of body make up they appeared to be 100% natural. She told me if she didn’t have connections these would be super expensive when I asked how much she smiled and said don’t ask baby your worth it I replied yes dear.
I returned shortly with a cocktail in my hand and sat it down on the end table next to the couch. I said well how do I look? She had me do the rotation so she could get the full view while sipping her drink. And said very sexy I like it a lot. She motioned for me to come closer which I did when I was face to face or shall I say crotch to face she lifted my nightie and sucked the head of my flaccid penis through my panties, the feeling was one of euphoria I placed my hand on her head and began softly stroking her long brown hair. She continued to suck my panty covered cock until It started to grow, she then held my hips and had me turn around. She commanded me to bend over, I did as she requested, and she grabbed my hips and pulled my panties down and started rimming my asshole. She knew that this was one of my weaknesses, the next thing I knew she was shoving a finger up my ass and began finger fucking me. I was loving it and she would reach around and grab my cock and stroke it and pull on it like she was trying to milk my cock for its cum. She asked in a sultry voice you like me fingering you baby, I moaned out oh yeah I do, without warning after she pulled out she inserted two fingers, this took me a little by surprise and I must have winced a little so she told me to just relax and let it happen.
I did as she asked took a deep breath and did my best to relax and she slowly inserted the two fingers and slowly fucked my asshole a little increased speed and fever. She started asking if her little bitch liked getting her ass fucked. I said oh yes baby I love getting fucked in the ass by you. She said good, unknowingly she had taken out a vibrator out of her big oversized bag and squeezed a little bit of gel on the tip and shoved it in my ass. I thought I was going to shoot across the room. She slapped my ass and saying relax! I’m not going to hurt you just breath. Again, I listened and relaxed which made it much easier to bare, I don’t want to mean that as being a bad thing, it’s just following her directions made it more enjoyable and I loved her assertiveness. After a few minutes of vibe fucking me she said bend over the ottoman and rest on your forearms. I did and she pulled my nightie up and told me to stay right there. She excused herself and went into the bathroom. I suspected she had needed to go tinkle as she always would.
Within a few minutes I heard the door opened and I could hear her walking across the living room floor. She walked up behind me and slapped my ass more than a few times, her slaps where firm and forceful this is something, to love doing to me because of how much it turned me on, with every slap it stung but it seemed that with every slap my cock grew. I so loved getting a spanking from a woman it brought out my submissive side but especially from her. I was thoroughly enjoying my spanking when she stopped the next thing, I know is I feel one hand on my ass cheek and I then felt something being inserted into my asshole. I stood up and placed my hands on the ottoman and turned to see her wearing a black strap on harness. She smiled her devilish smile at me and said you need to be really fucked and with her free hand she began guiding the 8”rubber dildo of her strap on into me. My natural reaction took over and I tensed up next thing I know is she slaps me hard on the ass and sternly saying relax! With that she proceeds to slip the rubber cock into my ass until the balls of it slapped against my ass. She then grabbed my hips with both hands firmly and began fucking my ass, slapping my ass at times saying you like taking it up the ass don’t you, you little whore. I was panting saying oh yes! Yes! Fuck me baby, you own me now. She loved my response. You’re fucking right I own you but seeing as how you like cock so much maybe we’ll find you a big black cock to fuck your tight little asshole. In my mind I was thinking oh fuck some big black bull is going to split me wide open. As enticing as it may have been, I was nowhere near able to take on such a challenge. She continued fucking me and suddenly, she starts to shake and saying oh fuck I’m cumming and is pounding my ass with the intensity of a jackhammer. She stops thrusting and I can feel her body shaking. I was to find out later that her strap on had a small clit vibrator on the inside as well as a dildo inserted into her pussy.
Her orgasm finally subsided, and she withdrew her rubber cock from my ass, she told me to get on my knees I was faced to face with her big cock, she peeled off the condom and threw it aside. She placed her hand on my head and said blow me bitch! As she shoved the head of her cock in my face yelling open your mouth you bitch, I want you to suck my cock now. A few of the same phrases I’ve used on her during rough sex. I opened my mouth and grabbed the shaft of her cock with one hand as I guided it in. My initial reaction was as expected I gagged on it. She had the presence of mind not to force it in my mouth or things surely wouldn’t have not gone well. I now mustered up all the cock sucking experiences I had in my life drawing on the experience of how many women’s mouth my cock has been in. I sucked on it as I bobbed my head in and out taking it a little deeper each time. She now had her hand on the top of my head softly stroking my hair, that’s a good girl suck my cock baby. Do you like when I feed you my cock. I simply nodded as best I could and muttered ah hmm in approval. She pulled it out of my mouth and slapped me across the face several times and said say it bitch, let me hear how much you love sucking my dick. On my knees subserviently I said Oh yes, I love your cock I love to suck you off please cum in my mouth for me please. She let out a soft moan oh that my good little whore. I went back to my blowjob and got into a rhythm of sucking and breathing and occasionally I would lick the head and entire length of the shaft I decided to kick it up a bit as I slipped a finger into her pussy and fingered fucked her finding her G-spot as I rubbed it she began a series of soft moans I could tell she hit the switch for the pussy vibrator as I could feel the vibrations in my mouth.
I glanced up and she had her hand on her clit working at getting herself off. Within a short time, she began to moan and her hips bucks to meet my sucking and she was actually fucking my mouth. I swear if it was a real cock, she was about to blow her load. She finally thrust her hips one last time and let out a moan, one could only assume by the all too familiar sound that she had gotten herself off.
When she was finished, she told me to lay back on the bed and observe, she picked up a small remote and turned on the video camera she had set up to record our fuck session, this was nothing new as we often enjoyed watching ourselves as if we were in a porn video, as she went to town sucking my now rock hard cock. She would stop occasionally and give me a brief explanation of what she was doing and why. You’ll see it will all come to you in due time. In the heat of her sucking my cock, she complimented me on doing a nice job then asked do you think you’d ever want to try the real thing. I was shocked and titillated at the same time, role play was one thing, but my girlfriend wanted me to suck dick. She continued her fantastic head giving skills until I shot my entire load in her mouth bucking my hips trying to get every drop of spunk down her throat. One thing DD loved was cum, I liked shooting it on her tits once in a while, but she thought it was such a waste.
She crawled up next to me in bed and kissed me on the mouth and shared her prize with me, something we’ve done many times but never after her asking me if I was interested in sucking dick. She was speaking to me in a soft sultry tone and asked so you never answered my question. I confessed that I did have a curiosity about doing it but never gave it much thought. She then said well if you feel like giving it a try, I can set something up with one of my friends. My immediate thought was she wants to cuckold me and have some guy fuck her brains out and have me suck his cock. I simply said oh do tell and what else is your friend going to want to do, she didn’t need to be a detective to know that I was a wee bit jealous and had no interest in seeing her get hammered by another guy, she laughed and said don’t worry I have friends with cocks who have no interest in me.
We continued or role play, always with over the top wild sex I couldn’t have asked for anything more well I was going to get more weather I liked it or not. The next day and early evening was a repeat of our typical weekend activities me playing my role of her shemale boy/girlfriend, but she had more in store. She decided we were going out cruising in her convertible that night and have a few a few drinks, our first or shall I say my first outing as a woman went much better than I ever expected it would so my comfort and confidence levels were high but going out at night was like an added level of security if you will. She had me put on a pair of her black stirrup pants and a pair of ankle high black boots, and one of her black lycra body suits, she applied my new lifelike breast forms with some adhesive whihc kept them in place so no wardrobe malfunctions and applied some body makeup to finish off her handiwork I slipped them into a black satin bra and had slipped my cock into the black satin gaff, the sole purpose of which was to hide my bulge and keep my cock from getting an erection and retain a smooth front like the women I was supposed to be she stepped back and took a look and, she tied my black button down blouse at the waist, my attire to say the least was not masculine at all, she even went as far as styling my hair longer but not quite shoulder length feminine looking which didn’t look that bad but she assisted me with my makeup and I looked pretty good not overly sexy or trashy but just very feminine looking after checking myself out in the full length mirror I was pleasantly pleased.
We hopped into her car and cruised around for a while it seemed when we stopped at traffic lights, we always garnered some attention, we took a ride out to one of the Truck Stops off the interstate we slowly cruised through the parking lot the entire time she was teasing me saying so wanna make an extra $50 and give a blowjob. I just looked at her saying I don’t think I’m ready yet. She said that’s ok but when you’re ready I really think it would be hot to see you suck a guy’s dick. I asked oh really, why, she said I just find it hot watching guys sucking cock, it would be extra hot if it was my boyfriend. I asked her so you’ve asked this of guys you’ve dated. She said yes but sadly no takers you’d be my first. Now for some reason that had a strange appeal that I would be the first guy to fulfil a fantasy of hers. She drove a little more and turned into a gravel parking lot saying let’s go have a drink I’m buying. I looked at her with the shocked deer in the headlights look, she laughed saying its ok you’ll be amongst friends here it’s a gay club. As if she flipped some kind of switch I was instantly more than ok with the way I looked and excited to go inside.
Holding hands as we went inside the dimly lit club with blaring music fucking disco or club dance music or some shit I’d never listen to, DD seemed to be at home. She told me these are some of my people and they are all cool, not cool isn’t tolerated here. We weren’t inside two minutes when this musclebound dyke dressed in a leather corset, black chaps, with short bleach blonde hair wearing a spike choker collar came up to DD and gave her a big kiss and not on the cheek hugging her and asking how she was its been a long time, she looked me up and down and not exactly sure what she thought of me by the pause that seemed to last forever she asked so is this your new toy? DD laughed and said no this is my boyfriend Bobby; he is indulging me tonight. Spike I’ll call her reached out her hand and said nice to meet you Bobby welcome to my club, watch this bitch she’s fucking crazy I laughed and said in a good sort of way. DD broke the ice by saying hey you two have something in common she looked at me and said Bobby has several Harley’s and knows everything about motorcycles. Spike was like no shit I ride a Sporty and we started talking bikes she asked me everything under the sun and I fired answers right back to her. She was thoroughly impressed, DD went off and got use a round of beers and shooters, when I asked what was the shot, she said don’t fucking worry about it just drink it. We had a few more rounds and I got more than a few looks from guys of course because women in this establishment had no interest in the men.
I had to excuse myself and asked Spike where the men’s room was, she laughed and said we don’t have one, the look on my face must have been priceless. DD said it’s a genderless restroom. Ok then so off I went to genderless land to pee. When I walked inside let’s just say the bar scene in Star Wars had nothing on this place. A guy was getting a blowjob in one of the stalls and some guy in a business suit who looked like an insurance salesman from Iowa was watching beating his meat. I stepped into one of the stalls pulled down my skin tight pants pulled down my gaff panty and straddled the bowl I was not sitting down in there no fucking way and let out a long steady stream of relief. I did my best to readjust my clothing while still in the stall. I exited the stall and walked over to the sink and washed my hands while doing so Mr. Insurance wanker was flailing his cock gawking at me, I was about ready to knock him out but remembered DD telling me everyone here was cool, so I just ignored him. Not everyone in here is a freak this good looking guy standing at the next sink said to me. I replied I guess not, he asked if it was my first time here and I told him yes. He asked if I was here alone, I said no I’m with my girlfriend. In there that could have meant anything or anyone, I guess. I dried my hands off and left, it took me a little while to make my way through the crowd to find DD.
While doing so I got my ass pinched and a hand cupped it for a nice healthy feel, remembering everyone in here is cool and I guess I should take it as a compliment. When I finally found her, it was apparent that her and Spike had a few more shooters while I was gone evident by all the empty shot glasses on the table. She laughed and said you’ve got some catching up to do baby leaning over giving me a big long tongue kiss saying you have no idea how happy you've made me tonight by coming here with me capped off by sticking her tounge in my mouth Then she said let’s dance and dragged me out to the dancefloor. I was keeping up with her the best I could but was no match for her I told her I’ll be right there pointing to the post by the dance floor. She nodded and continued to do her thing. I was standing there watching her and decided to step back a little off to the side and stood leaning on one of the tall tables.
The place was crowded, and you couldn’t help but contact another person so someone rubbing up against me wasn’t unusual. I was standing there and the next thing I know is I feel someone grinding up against my ass, I remained cool most likely do to the fact that I had consumed a large amount of alcohol, so I just went with it. I could feel an obvious bulge rubbing against my ass and seeing as I hadn’t resisted it must have been taken as a sign of approval, so the person continued. Subconsciously realizing what I was doing I leaned in such a way that my ass jutted out a bit more. My newfound admirer continued grinding his cock against my ass picking up the tempo as if to keep up with the beat of the blaring music and now there was no mistaking that I was getting dry humped right there in a crowded room full of people. I finally had to turn around to see who this was and when I did some strange guy who was with Mr. hot looking guy from the restroom just smiled at me. He reached out to me and led me to a dark corner of the room, Mr. Hot guy smiled and said it’s a little more private back here and his friend got behind me and had both hands on my hips and was pumping at my ass and not just a grind but a full on thrust. I still wasn’t protesting because I was getting more turned on by the second I allowed him to continue, and I must admit I was thoroughly enjoying the attention. I felt him tug at the waistline of my pants and attempted to pull them down. When I turned his cock was out in full view and fully erect. I was totally into it and loved anal play with my girlfriend but wasn’t going to allow this guy to ass fuck me in a club full of people. So, I took a step back put my hand out and pulled my pants back where they belonged and walked away. I found my way back to the table, where DD and her friend and a few others were partying. She asked me if I was ok and I said I was fine and had another drink and a shooter.
After maybe fifteen or twenty minutes passed, she came up to me and saying let’s get go home, I agreed and we said our good nights and left. We weren’t even out of the parking lot when I told her what had happened. She got extremely excited saying were you going to let him fuck you in the ass, I said no not in a room full of people, what about in private she asked, this is so fucking cool she said half in the bag as she was. I said I didn’t know, she asked what about a blowjob. I think possibly just to shut her up I said yeah if it was in private, I might have. She laughed a little saying wow this is so cool but hey not without me being there you little slut. I said ok you can watch no problem. We’re driving down this two lane road when the next thing I know she turns into the parking lot of this bar, I looked at her as if to say what are we doing here she smiled saying we’re going to find you a date. I just looked at her and she said don’t worry I used to come here with an old boyfriend years ago and its nothing but drunks. I was like ok nothing but drunks She said I’m going to go in and scope the place out and see if I can pick up some guy. I said that shouldn’t be a problem ah just one thing what happens when this guy realizes I’m a guy. She said I’ll keep him distracted and when it comes to getting a blowjob believe it or not, I think most guys don’t care they just want their cock sucked. So, she parked off in a dark corner and off she went in and true to her word she comes back maybe fifteen minutes later with this guy much younger than her who is stumbling so bad he can hardly walk. She must have gotten from him where he was parked, and I saw her walking him to his car. She motioned for me to come over, So I got out of the car and walked over to her and this guy. She introduced me as her sister and said please excuse her she has laryngitis so it’s hard for her to talk. He mumbled something
About your hot and he kept saying over and over to DD. She asked him if he wanted to party, my sister hasn’t had any cock in a very long time since her divorce would you mind terribly if she gives you a blow job. He blurted out hell no I’d be glad to help her out. This obvious bullshit line never would have worked on anyone other than some drunk, next thing I know is he is fumbling for his belt and DD says here let me help you but sit in your car first honey get comfortable. He sits in the passenger seat and she reclines it all the way back she then pulls his pants all the way down around his ankles and positions herself in such a way that his view of me is obstructed. I got down on my knees and I no sooner did I knew kneeling in a gravel parking lot was not a good idea. I yanked the floor may from under his feet threw it down on the ground and knelt on it. I took his limp cock from his underwear and proceeded to put it in my mouth. As soon as it touched my lips DD told me later that her face was beaming. I mustered up all my cock sucking skills that I had practiced on her and sucked and slurped at his lifeless cock. I figured let me get it all out and pulled his briefs down exposing his cock and balls. I went back to sucking him and licking it doing every trick in the book. He was enjoying himself obviously by the moans I was hearing. He said let me see her suck my cock I want to watch her. DD ran interference by jamming her tongue in his mouth telling me later all she could taste was beer, I continued sucking his cock and decided to let me stroke him hard, basically give him an handjob with his cock in my mouth. When DD decided to come up for air, he attempted to sit up to get a look at me, again DD thwarted his plans by popping open her blouse and shoving her big tits in his face. One of her weapons she used to get her what she wanted at work. He grabbed at them and sucked on them in a frenzy, he actually bit her tit he was so aggressive, she promptly slapped him in the face and said hey asshole no biting. I continued sucking and stroking and succeeded in getting this guy a little pass flaccid but no way hard enough to cum but I wasn’t giving up that easily I continued to suck his shaft my head bobbing up and down and I squeezed his balls and was pumping his shaft I finally got him fully hard but is seemed that as soon as I stop it deflated, dam it! I was so fucking close to giving my first real blowjob and this drunk wasn’t cumming through I looked up at her and shrugged my shoulders and whispered what am I doing wrong. She mouthed just give him a handjob. I did as she suggested and a handjob is something I know everything about and as hard as I tried no pun intended, I couldn’t get this guy’s cock hard. She finally said let me try I don’t know whether out of frustration of me not doing a good enough job or with this guy not being able to get it up.
She went down on him and furiously sucked his cock, stroking his shaft and squeezing it attempting to milk the cum from his balls but no luck. She stood up and just said fuck this guy isn’t going to get a hardon if I shoved a broomstick up his ass. She said let’s get the fuck out of here baby. We started to walk back to her car when he cried hey where are you going, come back here and finish sucking my bam, he fell back in the seat with his pants down around his ankles and his limp dick just lying there. She said sorry first guy had whiskey dick baby, I laughed and said no problem I’m sure you’ll help me find a working cock. She smiled and said you know it baby, now let’s go home and I’ll suck your cock, I replied only if you let me suck yours, she smiled and said deal. On our ride we shared a joint which was totally mellowing me out that combined with all I had consumed at the club I was feeling no pain home she had the look on her face, and I could tell her wheels were turning, she pulled over and sent someone a text message and we continued on our way. I asked what was that all about, she smiled and said you’ll see. When we pulled into her driveway there was a strange car parked out front and I should have been nervous but hey I just had a strange guys cock in my mouth and was feeling no pain. When we got out so did the occupant of the vehicle. As it turned out it was one of her guy friends from work, she smiled at me and kissed me and said this is Paul and he’s not drunk. My eyes must have widened in anticipation of what was instore he smiled and extended his hand and smiled hand in a very famine voice said my you look good enough to eat, I had to have blushed both from his compliment and the large amount of alcohol I had consumed. DD said well this is nice but let’s go in I don’t think the neighbors need a show. So, the three of us went inside. DD said why don’t you two get comfy while I fix us some drinks and she headed off. I sat next to Paul who was a complete gentlemen unlike the horndogs in the club.
We made small talk and he told me that DD told him we were at the club. I asked him if he went there and he said he had but it was a bit crowded and could get really crazy. I was relaxed was relaxed with Paul and told him what had happened to me and he gasped and said that’s just not cool. I said yeah, I know hey if I want to suck a guy’s cock or get fucked in the ass it will be on my terms. He laughed and said yeah, he felt the same way. I then told him what he already knew about DD picking up Mr. Whiskey Dick in the bar, he laughed and said things didn’t quite work out for you huh. I said no and I was this close, he smiled and said well I think I may be able to help you with that, and he stood up and unzipped his fly and pulled out a beautiful cock I didn’t ask but it had to be at least 8 inches. Yes, he was bold, and I was drunk but my girlfriend text him and let him know I was ready for some real cock and would he be willing to help. I was seated looking at this fine example of manhood right there in front of me but she was right I was finally ready hell I just had a cock in my mouth so I reached out and took his cock and began stroking it, he closed his eyes and said see how easy it is. I was stroking it and was so focused I didn’t realize my girlfriend was standing there watching us. She smiled saying I see you two have gotten acquainted I looked at her and smiled and never said a word and just kept stroking his cock. He said let me sit sweetie. I liked that he called me sweetie and complimented on how nicely I was dressed and how feminine I looked. He said that from his perspective in parking spot when I got out of the car, he had no idea I was a guy. That boosted my confidence 1000%. I continued stroking his cock until my instincts told me it was time, so I started to pull his pants down he kicked off his shoes and his pants followed he helped me remove his bright pink panties.
I had to compliment him on how cute they were, and I had several pair almost like them. The small talk was over, and I proceed to go down on his cock stroking and sucking his member and unlike the cock from approximately and hour ago it almost instantly reacted to my sucking. I could feel him getting harder and harder and before long I could taste his precum. I licked the head of his cock clean and licked up and down his rock hard shaft, the entire time he was moaning and saying oh my your good, are you sure you haven’t sucked a lot of dicks because honey you’re really that good. I looked up at him and smiled and said no and DD chimed in and said I’ve taught him well. Paul responded oh you sure have. With that I went back down on his cock and continued sucking him and stroking his cock. Out of the corner of my eye I saw DD and I positioned myself so I could get a better view and could see she was fingering herself with one hand and cupped one of her tits she had removed from her bra and was pinching her nipple. She saw me and got down on her knees next to me giving me words of encouragement. That’s is baby suck his cock, this is so fucking hot I’m soaking wet and so fucking horny you’re going to have to fuck my brains out!
Come on baby make him cum I want to see you make him cum suck his dick baby you know you want his hot load. There was no question I going to make Paul cum, and I was laser focused on doing just that. I stopped stroking his cock and went on full suck mode. I love any blowjob, but a really good blowjob is when your cock is sucked clean by mouth only not a handjob with a dick in someone’s mouth. I figure I’m a guy and this is how I like it so other guys like it that way too. I was now bobbing up and down on Paul’s cock and had increased my speed and intensity of my sucking exactly as my girlfriend does when she is intent on making me finally cum. Paul was moaning and saying oh God oh my God I’m going to cum sweetie I’m going to cum and without skipping a beat DD was like a cheerleader at sporting event come on baby suck him off make him cum she yelled!
Paul’s body began to shudder and shake, and he let out a load moan and released a load of hot steaming cum from the head of his cock. DD knew the signs and said suck him baby swallow his load like I taught you. I did my best to swallow his load but a little escaped my mouth and was dribbling down my chin and was on my lips. DD swooped in and kissed me intently licking the cum from my lips and chin. She kept kissing me and saying oh my God thank you , thank you for doing this for me baby I love you. I smiled at her and said I love you too, she laughed and said now eat my pussy and fuck me I need it bad. I looked up at Paul who was spent from my cock sucking my cock was now hard as a rock and I needed some relief looking at Dee pointing to the other couch Still fully dressed fem I proceeded to just pull down my pants and slip my cock into her super wet pussy. I was pounding her pussy for all I was worth when Paul said I normally I’m not one for this, but you guys are fucking hot you’re a couple of animals. I pumped DD’s pussy like a jackhammer and after maybe 15 minutes I filled her pussy full of cum and pulled out of her and went down on her lapping my own cum from her pussy something I do most of the time while doing so I brought her to a screaming orgasam I looked at Paul and looking at her for approval and just asked if he would like to join me, he thanked me for the offer but said he was good with just watching the two of us. DD later on that night told me she couldn’t believe that me Mr. jealous had asked another man if he wanted to lick his girlfriend’s pussy, she laughed and said she wasn’t mad just surprised. The three of us sat on the couch, I kissed her neck and whispered would you mind, I didn’t even half to finish my sentence when she asked Paul would if he would mind fucking my boyfriend in the ass. My little slut is hungry for some man cock what do you say she asked. He laughed and smiled and said who am I to disappoint a lady.
