My girlfriend is a domineering bitch, and I love her for it. I initially wondered how I got myself in this situation, but I have read many stories and seen videos and pictures as well as met many other men who are my exact predicament. (Predicament may be too harsh of a word since I am a willing participant). I was 18 when I met Janet (she was 28). We met like a lot of other couples, making googly eyes with each other from across a crowded bar. We made small talk and traded phone numbers and went out on a date the next week. She was a perfect lady; we didn't even have sex until about three months of dating. I think Janet enjoyed herself a lot during that first three months, as it turns out she was grooming me for my future. She always dressed very sexy and was a huge tease, always showing me her shiny panties or her sexy garter belt or other lingerie. (You can probably guess that I had a pretty hard time those first 3 months). This woman had the largest collection of lingerie and sexy clothes that I had ever seen. I would have sworn she owned a catalog or warehouse. The thing that drove me absolutely over the edge every time we went out on a date was that she always had on a garter belt, stockings, high heels and a mini skirt. (And she always made a point of showing me, but not giving me any). She would flash me a shot of her stocking tops while driving in the car, or if we were across the room from each other she would coyly pull up her skirt so I could see her panties and garters. I was surprised by how long we waited to have sex because of how she dressed and acted. She is an incredible flirt and whenever we were around any guys she would flirt with them like crazy. She is also very touchy with men, I thought she might be trying to make me jealous, but it just made me hot for her. Waiting to have sex with Janet was definitely worth it. This woman is the wildest and most adventurous woman I have ever met. Our first experience went all night long and she changed her lingerie outfit at least three times. She introduced me to vibrators, dildos, vinyl, leather, lubrication, anal play and anything else you can think of. This all happened on the very first night we spent together. While she was giving me head, she put her finger in my ass; I had never felt anything like it. She was swirling it around and pushing it in and out and I came in her mouth. "Oh, you like having your ass played with? I have many more fun surprises in store." She grabbed one of the many vibrators that were on the bed, put some lube on it and started sliding it in and out of my ass (she was stroking my cock at the same time). I got hard again immediately. "I knew you would like that" she said. She stopped for a moment and asked if I would indulge her. At that point I think I would have agreed to anything and I said "of course I will indulge you. What do you have in mind?" "I've always fantasized about having a lesbian experience, but never had the nerve. Will you help me with my fantasy?" "How do you propose I do that?" I asked. "I have all this lingerie and all these toys, we'll just dress each other up and I'll pretend your ass is a pussy (don't worry, I won't forget about your cock). It was at this point that I made my biggest mistake, when I uttered the words; "OK, I'm game". She asked me what outfit I wanted her in (and since she was already dressed in a red vinyl garter belt with matching shelf bra and black hose with shiny 5 inch boots) I said I was good. She said the first thing we need to do is make you look like a woman. She went to her closet and pulled out a wig more than shoulder length and strawberry blond. I asked if she always kept wigs lying around and she replied "with a wig I can be a completely different person...and so can you." After she put the wig on me she chose a pink satin corset that had white ruffles around the bottom, white hose and a pair of black heels with a 6 inch heel (we had roughly the same size heel although they were a little tight). While I was struggling through trying to put on this outfit, I was watching as Janet was cinching up a 7 inch strap on dildo. She noticed I was watching and said "don't worry; I'll be gentle...at first". She had me lay on my side on the bed and she was positioned on her knees up by my head so that the dildo was right in front of my mouth. She lubed up her right hand and started stroking my cock and told me to start sucking hers. As I was sucking her off she was playing with her pussy with her left hand while she was thrusting her hips to move the plastic cock in and out of my mouth. She was moaning as she was fingering her clit, then I heard her say "oooh I love watching you suck that cock, I wish you were sucking a real cock. Please, please tell me you want to suck a real cock!" I wanted to make her happy and more importantly I wanted to her to cum. I heard the words as they left my mouth "I want to suck a real cock, please let me milk a real cock and swallow that cum." Janet started to cum; she let out a squeal and thrust her head back. I could see her juices running down her thigh and collecting at the top of her stocking. As the rush from her orgasm subsided she started moving her hips again and pushing her cock past my lips. "That got me so hot, I love watching you suck it, I can't wait to see you suck a real cock. We'll do it together at first and I'll teach you all I know." Was she serious! We were just playing games; I was only telling her what she wanted to hear to get her off. She didn't really believe that I wanted to suck off some guy. She lay down and began nodding off, but the last thing she said was "I can't wait."
The next morning I was startled by Janet stroking my already hard cock. We were both still dressed in lingerie and that feeling alone was enough to get my cock hard. I loved the silky smooth stockings that encased my legs and the garters that were attached to the satin corset made me feel very sexy, and the high heels just added an element I can't explain. "So?" Janet asked as she stroked my cock. "When do I get to see this happen for real?" "You weren't really serious were you? I thought we were just playing bedroom games." "Oh, where is your sense of adventure?" she said. "Besides, you can't tell me that you didn't enjoy your experience. Can you?" I had to admit to her that I loved the outfit I was wearing and that I did like her thrusting her cock into my mouth. "Just think about that only with the added element of swallowing a load of cum." "What do you want me to do I said, just walk up to some guy dressed like this and say hey, do you mind if I suck your dick?" She told me to leave that part up to her and that she would arrange everything. She said she knew a guy she used to date would probably be up for that kind of scene if she promised him something in return. I admitted to Janet that I was very excited about the idea but also very scared. She said the reason I was scared is that I wasn't prepared and that she would help me with a few lessons. "First, you should find out what guys cum tastes like so you know what to expect." She went down on me and made me cum in her mouth within a minute, she then put her mouth over mine, kissed me hard and let my cum spill into my mouth and down my throat. "See that wasn't so bad was it? It will come out a lot faster though when you actually make the guy cum. You should also practice getting in and out of your lingerie as well as walking around in heels. I obviously have plenty of lingerie and heels for you to use while you practice. Since it's the weekend, you can just stay dressed up all the time. We will need to find some skirts and tops for you though, just leave that up to me." That weekend I must have tried on a million different outfits; garter belts, corsets, waist cinchers, high heeled boots, leather and vinyl skirts, satin tops and about 6 different wigs.
I left her house late Sunday night and didn't talk to her again until mid week and by then I had mixed feelings about what Janet wanted me to do, although I had an overwhelming desire to be dressed in a nice satin garter belt, stockings and heels. I didn't even feel comfortable in my male clothes. We talked late Wednesday and Janet said she had everything set up for Saturday. I explained to her my apprehension but also made the mistake of telling her that I missed being dressed in lingerie. "Everything will be fine" she said. "I'll be with you every step of the way. I want you to think of this as a fun adventurous experience, not something to be scared about." I also asked her how she convinced a guy to let another guy suck him off. She said "are you kidding? All I had to do was tell Cody that two "girls" quote unquote would like to give him head at the same time. You know that all guys are pigs. I also promised him another special favor but I'll tell you about that at another time. I hope that eases your concerns." She then proceeded to give me all the details and told me to meet at her house at about 10 AM on Saturday. When I arrived Janet was already dressed for the day and man did she look hot. She was wearing a tight black wet look skirt and black stockings and silver knee high boots with a 5 inch heel. She also had on a wig that made her look like a red head. She also had the outfit laid out that I was to wear. It consisted of a purple satin garter belt with pink polka dots, pink satin panties, white stockings and black 6 inch heels with a two inch platform. For my outerwear she chose a black layered taffeta skirt, pink camisole and a white jacket. She also chose a strawberry blond wig with pigtails. After I was finished dressing and Janet had put on the wig and some eye shadow, she took me over to the mirror and I was amazed. I thought I was looking at a female slut in the mirror; there was no resemblance of a male at all. "You're ready" she said. We got to Cody's house at about 4 that afternoon and when we walked in she didn't introduce me. Janet didn't even try for an ice breaker conversation, she just said "well Cody, are you ready to help my little slut with her first cocksucking experience?" He replied with "yeah bitches, suck my cock." Janet and I both got on our knees in front of him and she unfastened his pants and pulled out his cock. It was normal size and nothing impressive. "Follow my lead" Janet said as she took his erect cock in her hand and led it to her mouth. I watch for a few seconds and then she took it out of her mouth and pointed it at me. I opened my mouth and she guided his cock and she stroked him while I sucked. She was really getting into it as was I. She was rubbing her pussy with her free hand encouraging me by saying "you are turning me on so much I can hardly stand it" Cody chimed in "you finally got one of your boyfriends to be a sissy cocksucker Janet...good for you." Saying that I was enjoying myself was an understatement and Cody also seemed to enjoy himself and he said he was about to cum. Janet took her hand off his cock and let me take over completely. I stroked and sucked to his deep breathing. I felt him tense up and then his cock exploded in my mouth. It was such an exhilarating feeling. I swallowed as much as I could but cum was gushing out the corners of my mouth. At that moment I felt so sexy, so liberated. Cody patted me on the head and said "not bad for your first time, I bet my buddies would love you." Buddies? Oh what were the chances that I could do this more than once? But I dare not speak, Janet gave me implicate instructions not to utter a word. She must have been reading my mind though because she spoke up saying "buddies eh? Can you get a hold of these buddies? If you do maybe I can give you that special favor while our little friend here is busy with her cocksucking lessons." "Anything for you Janet" he said as he raced toward the phone. While he was gone Janet told me that I could thank her later for setting up this arrangement with Cody and his friends. She also said that she had to pull some strings to make it happen and one of them was the special favor she promised Cody. "I told him that if he let me bring you over here to service him that I would let him fuck me." My mouth dropped. Janet saw my surprise and said "don't worry honey; I'll make him wear a condom. How about if you think about it like this. Just picture yourself watching a live porno with some redheaded slut and not your brown haired green eyed girlfriend. Beside, it's not like I haven't had sex with him before." Before we could finish our conversation Cody came back into the room. "Three of my friends are just sitting around doing nothing. I told them he was a dude and all, but I also said they would get a pretty good blowjob. I also told them that was probably the only proposition they were going to get and they said a blowjob from a dude that looks like a slutty chick was better than no blowjob at all. They'll be here in ten." Janet had me kneel on the floor at one end of the couch while she called Cody over to the other end and they started kissing. He has his hands all over her body and even pulled up her skirt to reveal the shiny red garter belt she was wearing. "Let's not get too heavy yet, we don't want to spoil the party for your friends." The three of them walked in two minutes later and Janet explained to them how this was going to go down. "You guys are going to all get a blowjob from her (she pointed at me) but you also get a bonus because you get to watch Cody and I fuck each other." One of the guys said he wasn't comfortable whipping his dick out and standing in a circle taking turns with his buddies. "Fine" Janet said. "You can all sit in different chairs around the room and you can each have equal time with her." They each took different seats around the room and Janet said "let's get this party started." I slid up to the first guy who was sitting at the end of the couch and pulled his pants down around his ankles. I was feeling very arrogant and sexy since I had made Cody cum so quick so I thought I would play it up and I batted my eyes and then looked longingly into his eyes as I slowly engulfed his cock (I know that guys love it when the girl looks up at him with his cock in her mouth...trust me). Meanwhile I could see out of the corner of my eye that Janet had hiked her skirt up and knelt and the couch facing the back of it. Cody wasted no time and pulled her panties aside and slowly entered her from behind...they both let out a sigh. The way I was positioned on the floor I knew that my garters were showing as well as my pink panty covered ass, and it really turned me on, especially know that the other two guys were probably turned on looking at my garters and panties...I shook my ass slightly for effect. I was so turned on. Sucking on one cock and knowing that I had two more in the wings and watching my girlfriend get fucked by a guy I sucked off just a few minutes before. I continued sucking and decided to turn into a complete slut making groaning noises and slurping sounds. One of the guys had gotten up off the chair and went behind the couch and was dangling his hard cock in front of Janet's face. She quickly took it in her mouth...I was jealous, that was my cock and she had better not make him cum...that cum was for me. While that was going on I felt a hand on my ass...what was up with that, didn't these guys know I was male. I was so hot I didn't care and I assumed he was touching my ass because I had turned him on with my wiggling in my sexy lingerie. The guy on the couch getting a nasty blowjob came in my mouth, and Janet sent the other guy over to me (I swear this women can read my thoughts). I don't know what I was thinking but I told the guy that was playing with my ass that he could fuck my virgin ass so long as he used lube and a condom. I went back to the duties at hand and started sucking off guy number two and by now Cody and Janet had finished and were just watching us. I think that Janet was really excited that her understudy (me) was taking such initiative. While I was again sucking like a slut the guy behind me was tugging at my pink panties. He pulled them down, lubed up his dick and started pushing at my asshole. It didn't even hurt. Janet told him to go easy on me because I was a virgin. "she doesn't suck like a virgin" said guy number two as he blasted a load of cum down my throat...this time I didn't spill a drop. I was being ass pounded slow and steady and Janet came over and sat on the couch right in front of me and offered me her pussy. "You seemed to have acquired a taste for cum, I certainly don't want to deny you. In fact" she said as she looked over me, "don't cum in his ass, I want him to swallow your load." This party went on for hours and not only did every guy get another blowjob from me but they all fucked Janet while I watched and masturbated myself to orgasm. After that night I told Janet I didn't know how I was going to go back to dressing like a man. "Maybe you don't have to." "Go on" I said. "Well I need a new office secretary at my office. The criteria for the job include but are not limited to the following; she must wear stockings, garter belts, very high heels and mini skirts. She must also be able to service my clients and take dick-tation. Do you think you can do that?" "With pleasure!" I said. "You're hired."
The End