I had finally met a woman who not only accepted my crossdressing fetish but encouraged and nurtured it making it a part of not only or sex life but our life as a couple in general. We had a strange dynamic not only were we boyfriend and girlfriend, but we were best girlfriends as well. When I dressed fem, which was for the most part the majority of the nights after work and almost the entire weekend with very few exceptions I became my female persona. We enjoyed shopping for cloths and lingerie in shops and malls innocently enough as two lovers sometimes do but my fetish/our obsession was our dirty little secret eventually ensuring enough confidence in me to go out in public fully passable which we often did and every minute of which was enjoyable beyond description. This is how it began...


It was one night a year or so into the relationship when one night at her house I just got there when she was arriving from work we went inside and she kicked off her shoes put her feet up on the ottoman and asked if I would rub her feet, something I am really great at according to every women I’ve been with. So, I’m there rubbing her feet and she undoes the belt of her dress, and opens it giving me full view of her uncovered pussy and her matching of course bright red bra and garter belt. She said help me off with this thing will you please. So, she sits up and I place my arms around her back and unhooked her bra as she kissed me. She let out a sigh of relief. She said I hate wearing these damn things sometimes they can be so uncomfortable, I laughed and said quit your bitchin how bad can it be to look that damned sexy. She laughed and said ok, so you think it’s easy huh. I laughed yup. She got up from the chair and sauntered off to the bedroom her open dress flowing and her tits bouncing, she returned with a purple padded bra and said here you go put it on. I looked at her and she said you heard me put it on now! I said ok no problem. I peeled off my shirt and threw it on the chair. She said ok now put it on, I didn’t do the reverse trick and then slip your arms in as I do at home. She steps behind me and hooks the bra closed putting a finger in between the strap and my back giving it a little tug. She turned me around and said ok now do the runway walk for me and show me how sexy you look. I did as she asked and she kissed me and said you look hot and throws me my shirt, put it on your taking me to dinner wearing that so we’ll see how comfortable it is.  Half jokingly I said what no panties. She said ok smart ass take your pants off and back to the bedroom she goes returning now with a purple satin garter belt that matched the bra and a pair of black stockings. She threw me the garter belt and said you know how to take it off I’m sure you can figure out how to put it on, which I did with ease. She pointed at the ottoman and said sit! I did as commanded and she put on one stocking at a time rolling it up my leg until it was just high enough on my upper thigh and affixed them to the garters and snapped the clasp closed. She pointed, saying walk and I did as she ordered. She told me to do a turnaround as she picked up her bra and put it back on.


 She said you look sexy as hell now put your pants on and take me to dinner you slut. We went out and I was completely at ease with it and comfort wasn’t an issue the set  was really good/expensive so it aided greatly to the comfort level and the nylon stockings felt fantastic and the spirit of us matching outfits I wasn’t wearing any panties which I would have naturally done at home. She told me she was thoroughly impressed we enjoyed more than a few cocktails with dinner seeing how it was a Friday night and we didn’t have to work the next day. When we got back to her place the first thing she did was undress and while standing there completely naked she looked at me and said are you going to, stopped and said no keep them on I kind of like it, it will be like fucking a shemale. Told you she was raunchy at times. We fucked and sucked, and I was clearly the sub. She got into it right away calling me her bitch telling me to eat her pussy clean of cum whenever I dumped a load into her. Sucking on my bra covered tits and pinching my nipples.


We both enjoyed my playing the role of her shemale girlfriend so much that we continued for weeks 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 had found me a very realistic pair of silicone implants which added a nice giggle to my tits when I moved, 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 twirl 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 said relax I’m not going to hurt you just breath. Again, I listened and relaxed which made it much more tolerable. 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 say after drinking a few.


Within a few minutes I heard the door opened and I could hear the sound of her heels walking across the living room floor. She walked up behind me and slapped my ass a few times with every slap it stung but it seemed that with every slap my cock grew. I so loved getting spanking from a woman especially 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 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 said 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 wither 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 mouths 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 cold 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 could tell she hit the switch for the pussy viberator as I could feel the vibrations in my mouth. I glanced up and she had her hand in her pussy 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 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 occasionally, 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. My immediate 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.  She decided we were going out cruising in her convertible one night and have a few a few drinks, not yet being comfortable enough to go out in full drag she had me put on a pair of her black stirrup pants and a pair of ankle high black boots, a one of her black lycra body suits, I had on a black satin bra she stepped back and took a look and said here and handed me two silicon pads and instructed me to stuff them in my bra, she tied my black button down shirt at the waist, my attire to say the least was not masculine at all, she even wet as far as styling my hair longer but not quite shoulder length feminine looking which didn’t look that bad but I was clearly not passable just very feminine looking, we hopped into her car. 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 Truckstop 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 when you’re ready, but 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 guy’s 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 her. 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 bar. Like she flipped some kind of switch I was good with that.


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 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 skintight pants and straddled the bowl I was not sitting down in her 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 relied 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. I 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. 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 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 make contact with 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. Without realizing what I was doing I leaned in such a way that my ass jutted out a bit more. My new found admirer continued grinding his cock against my ass picking up the tempo and now there was no mistaking that I was getting dry humped right there in a 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 in the restroom just smiled at me. He reached out to me and led me to a dark corner of the room, Mr. Hot gu 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 my a full on thrust. I still wasn’t protesting so he continued, and I must admit I was thoroughly enjoying the attention. I felt him tug at the waist line 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 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. I said I didn’t know 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. So, she parked off in a dark corner and off she went 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 my 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 form 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 hear. 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 but popping up 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. 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 you are 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 laying 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.

Bob Long
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