This story is partially based on a true story and is partially imagined. I leave it up to you to guess where the truth ends and where the fantasy begins.
Hi, my name is George and at the time this story occurred (within the past 3 years), I was 19 years old, 5'10 and maybe 200lb (so not tiny, but not really fat either). Also, I am white. A little background about me: I generally did consider myself straight, because even though I was also attracted to men (about a quarter of the time), I never had much desire for an emotional relationship with a man. I only wanted sex. At the time of this story, I was a virgin. I had had some heavy petting with a couple of my ex-girlfriends (only one time of which got me off) and once while drunk, a guy friend and I watched each other masturbate, but that was about it as far as sex goes. This isn't one of those stories where I realized I was really gay at heart and not attracted to women. I still love sex with women...maybe even slightly more than with a man.
In fact, I love (and loved) the female body SO much, that a woman in any state of undress would turn me on in an instant. When I was young and didn't quite know how to find pictures of nude women, I looked at women in lingerie and got incredibly turned on. Once while in the laundry room, I tried on one of my mother's bras and realized that wearing women's clothes gave me a similar kind of rush. I would just get hard right away. I started sneaking around and wearing her panties, bras and pantyhose soon after I started masturbating. It was just too hard to keep away from. For a long time, there was absolutely no desire for guys. I just liked wearing my mom's underwear and sometimes her other clothing (none of it was very sexy). Eventually I started fantasizing about going out in drag. The thought just made me feel so sexy. I also imagined just turning OTHER people on while in drag and that just turned me on more. Of course, I soon after realized that the people I turned on would be other guys...and it just didn't bother me at all. Turning other people on was turning other people on...I was sexy either way. Of course, this was all fantasy. I have also fantasized about actually being a girl and it really turned me on, but I have never really had the desire to change sexes or anything...I like being a guy too.
So one thing led to another and in my fantasies, I started giving blowjobs and once I found porn, I looked at gay porn as well as straight. The concept of a nice big (usually black) cock in my mouth just turned me on SO much, but I was definitely considered a "good, quiet, kid" and I definitely never had the nerve to go do anything. Once I could drive, I started buying some of my own lingerie that I could enjoy by myself. A couple of times, I wore panties to school, but that was risky business and I ended up being more nervous than turned on, so I stopped. I realized that people like me generally liked to be bottoms and I really liked the concept, but I didn't know how it would feel. As soon as I turned 18, I went to a couple of sex shops and got a dildo and a butt plug. I would stretch myself out and would masturbate with them. The concept turned me on SO much, but it always really hurt (even after a lot of stretching and practice), so I wasn't sure whether I would want to be a top or bottom.
I started reading stories and found out that the people who like people like me (in lingerie), are generally older "daddy" types, so in my fantasies, I started thinking about older, (fatter), guys and after a while that really turned me on as well. Keep in mind that I still have just as many, if not more straight fantasies, so these did not always overwhelm my thoughts...though they did sometimes.
One time, I decided to go to the local adult bookstore. I went in and masturbated in the big theater and then waited until I was ready to go again and decided to try one of the booths. I of course knew all about glory holes. I quickly snuck into one (there were plenty of guys around, but I didn't want to attract too much attention). I started masturbating to the screen and after 3 or 4 minutes someone entered the booth next to me and stuck their finger through and said "Come on...stick that cock through." Well I was so excited and nervous that I just blew my load right there and ran out of the place in embarrassment.
Over the next year or two, nothing really happened. I bought a few more lingerie outfits, a few of which were really sexy. Once I got into college, I would periodically wear panties under my regular clothes, but I never got caught. Every once in a while I would dress up and get on a gay webcam chatroom and find some older guy to talk and masturbate with. I really enjoyed it, but even THEN, I still got really nervous.
So this story begins during the summer before my sophomore year in college. I was driving by myself up to some of my extended family up in Michigan. I enjoy long drives by myself and this one was no exception (it was really the first one I ever did). I always had this fantasy where while on the road, I would stop at a gas station or rest stop. I would be wearing lingerie under my regular clothes, but in a way that it was really obvious...like a black or bright bra under a thin white shirt and panties that stuck out of the top of my shorts. In the more tame fantasies, people would just stare or maybe smile and just their knowledge of my secret would turn me on. In the more wild ones, a trucker or fellow traveler would grab my ass and bring me somewhere to have their way with me. If the latter were to actually occur, I wasn't sure I would go through with it, but it still turned me on.
I didn't actually bring any lingerie on the trip, so I stopped at a wal mart supercenter (it's the BEST place to buy ladies underwear because there is a lot of it, it is cheap, and there are so many people so it is easy to blend in). I ended up buying a really sexy black and light blue lace push-up bra and a cute, black and pink, g-string (what better to advertise to people?). I stopped at a nearby gas station to change and just left my undershirt on over the bra. I bought something from the store I didn't really need and got one stare, but that was it...kind of a let-down.
I got back on the road and didn't drive more than 50 miles before I saw one of those huge adult, megastores on the side of the interstate and I happened to be pretty turned on (by what I was wearing), so I got off on the next exit. I parked and ended up putting my t-shirt back on over my undershirt because I was pretty nervous and wanted to be subtle with my attention seeking. I got of the car and entered the store. Right in the front were huge racks of really sexy lingerie and costumes. I started there and examined everything closely, not really caring if people thought I was considering them for myself. Unfortunately though, it was all WAY overpriced, so I decided against it. Next, I headed over to the porn section. There were a few guys there and I made it a point to bend over and show my g-string a couple of times, but no one took the bait. The porn too was pretty expensive. So finally, I went to the desk and asked how much the theater/booths were. The clerk told me that there was a special and both together were 15 dollars. This was a little steep for me (I AM a poor college student), but I couldn't pass it up. I paid and headed into the main theater.
The main theater was pretty much what you would expect...large, dark and dingy. When I entered there was one other guy in the theater and I ended up sitting across the aisle and one or two rows back from him. Right when I stepped in, on the screen was a built black guy ramming his huge cock into a small, blonde girl. It was a pretty well done porno and something about having it up there so big and loud turned me on pretty good. Once I sat down, I examined my surroundings and started stroking my cock through my shorts. I noticed the man periodically stealing glances at me and I would periodically glance back, not hiding the fact that I was stroking through my shorts. I got a good look at him, he was a white male, probably late 50's, early 60's. He was overweight, but not incredibly fat and he was wearing a baseball cap.
After maybe 5 minutes of this, periodically trading glances, he got up and slowly walked over to me and very gently asked "Do you mind if I sit with you?" and I answered "No, of course not," though my heart was pounding incredibly hard. He sat down and introduced himself as Jack and I told him my name and we shook hands. He may or may not have started with a minute of small talk...I don't remember...What I do remember is that he reached his hand over and slowly started stroking my leg. Just that made me feel so great and even more turned on. The only thing that kept me from blowing my load right then was being really nervous. As he rubbed my leg, he started saying things like "Do you like the video?...does his big cock in her wet pussy turn you on?" clearly trying to turn me on (as if that was necessary).
Slowly, he put his left arm around me and starting stroking my leg with his right hand. He would periodically brush my cock, but he would never linger. This drove me CRAZY, which is why I suppose he did it. He started stroking a bit more of my body and slowly made his way up past my stomach to my chest (it was all on the outside of my shirt). As his hands got closer and closer to the bra, my heart started pounding more and more. How would he react when he discovered I was wearing a bra? Would he be disgusted? Would he make fun of me?...
Finally his hand reached my chest and started lightly rubbing one of my nipples. Of course, I had a push-up bra on, so I could barely feel it. After maybe 10 seconds, he stopped, clearly confused. He moved his hand around, exploring the area. He outlined the bra straps and I became terrified of what he would do. He paused for a few more seconds and grabbed and massaged my breast as if I were a girl. But this didn't last very long and he soon moved back down to my legs. He kept rubbing me for a couple more minutes, whispering things to me to turn me on and calm me down (I must have been clearly nervous). Eventually he asked "Do you think I could maybe see your cock?" I said yes and slowly undid my fly and pulled out my cock. My cock is about average (6.5", maybe 7") and is cut. In the process of pulling it out, I wasn't sure if he noticed the panties I was wearing, but it was pretty dark in the theater, so I kind of doubted it. He reached over and slowly started stroking my cock. It felt so great...I had never quite felt anything like it before.
So there I was in an adult theater, wearing lingerie and an old man was sitting right next to me stroking my manhood and periodically rubbing other places. Though I was still incredibly nervous and still unsure of what to do, I reached my hand over and started stroking the inside of his thigh. He didn't really react very much, but I felt like it was something I should do (it only seemed fair). We went on like this for a bit more. We would periodically talk and despite the events, he just treated me like a straight guy who just wanted some attention. By this point the first video had ended and I believe a gangbang scene came on, though I'm not 100% sure...I was a bit distracted.
Eventually he slowly turned his baseball cap backwards, pulled his arm from around me and leaned over and put my cock in his mouth. I can't even describe how amazing it felt (I'm sure you all remember your first good blowjob, so just think of that). It was just so soft and warm and wet and I just felt like I was in heaven. Though I was incredibly turned on, I actually wasn't about to blow my load right away, so I was able to enjoy the experience for a while. He kept going for a bit, but I have absolutely no clue for how long. I completely lost track of time. It could have just been a couple of minutes, but it also felt like it could have been hours. After a while, I was getting pretty close to orgasm and he suddenly pulled his mouth off and grabbed my cock with his hand, but didn't start stroking. Of course, this was absolute torture for me and I wanted nothing more than to just finish with my orgasm. He asked me "Do you want me to finish?" I nodded and gave a very wimpy "Yes." And he responded, "Okay, I will in a little." I of course had no idea what that meant, but my heart dropped. I just wanted to get off.
He then surprisingly, somewhat sternly commanded, "Get on your knees." I didn't know what to do or how to respond. I of course knew what would happen next, but I wasn't quite sure if I was ready to GIVE a blowjob. Of course, it only seems fair, but the entire time, he seemed perfectly happy just pleasing me and I assumed he was one of those guys you read about who just wants to "blow and go." I started to stutter a protest, but he quickly stopped me and said "Come on sissyboy, get on your knees and suck daddy's cock." As he said that, he pulled down his zipper and pulled out his cock. I gasped a dumbfounded "What?!" and he answered "Don't think I don't know. I felt your bra and I saw your cute little panties when you pulled your cock out. You're a horny little sissyboy, aren't you?" I sat there shocked for a second. Of course, I knew this is the kind of role that panty wearing guys tended to fall into and I had read plenty of erotic stories where this happened. I had even roleplayed over webcam, calling myself a "sissyboy" or "girl" and calling my older male partner "daddy." I just wasn't sure if I was ready to head into this full on, because I wasn't sure where it would go or if I would be comfortable with it. So I knew at this point I could either wholeheartedly play along or just quickly leave and call it quits.
I was still incredibly horny, because I had never had a chance to actually get off and my hormones were raging, so I decided to take the plunge. I got down on my knees and as I did so, I answered "Yes daddy, I'm a sissyboy," It felt like an odd, weird, forced thing to say, like one of those bad porn lines, but in another very real sense, it just felt right. I had never seen another guy's cock close up, so this was all very new to me. He wasn't quite as big as me...maybe 6" or so, but he was a little thicker. I wasn't sure what to do, but I remembered reading lots of warnings to not use any teeth, so I covered up my teeth with my lips, leaned forward and stuck his cock in my mouth. He wasn't quite hard get, but as soon as I got his cock in my mouth, something just felt right and I got even more turned on. I just loved being in this submissive position, wearing women's underwear, with a cock in my mouth. It felt great. His cock tasted a bit salty from sweat and maybe precum, but it truly did taste great. I started moving up and down and massaged his balls and base of his cock with my hand. In just a minute or so he was rock hard. He started quietly moaning and saying things like "Oh, suck it, little sissy." After just a couple minutes of this, he reached down and helped pull off my shirt so my bra was exposed. He tried to grab and massage my breasts, but it was an odd, awkward angle, so he ended up giving up so I could resume sucking him.
He kept giving me dirty talk and called me "his girl" a couple of times. At one point, he forced my head down really far onto his cock until I gagged. I didn't throw up or anything, but it did freak me out for a second. However, once I got used to such a big thing in my mouth, I started trying to see how much I could get in. I didn't quite have the technique right, but I did deepthroat him for a bit. I started bobbing up and down really fast and working his cock with my tongue. I was really getting into it and judging my his moans, I could tell he was as well. I think he was getting pretty close to cumming, but he reached down and stopped me and slowly stroked my chin so I would look up at him. He calmly said "George is no name for a girl. Is there any other name you would like to be called?" I thought for a second and responded "Well, I've always like the name Jessica." He said "Ahhh, I like that too. Okay, from now on I'm going to call you Jessica." I nodded in understanding and he said "Okay, Jessica, why don't you stand up for me."
I slowly stood up, facing him and he said "now take off your pants." I gave him a quizzical look and wasn't sure if I should, but he continued "You wouldn't have bought such cute panties if you didn't want SOMEONE to see them." I couldn't deny that logic, so I slipped my pants down (they were already un-buttoned and un-zippered from when I was getting sucked). While I did so, I tucked my cock between my legs, so it wouldn't be sticking out. Obviously, a g-string doesn't have a lot of fabric covering the front, but there is enough that when I am soft and un-aroused, my manhood is completely covered (though there is of course a very noticeable bulge). However, as soon as I get a bit erect, my cock will stick out the side of the panties. Though I didn't think Jack would really care...It just didn't quite seem "lady-like" to have my cock sticking out.
Amazingly, no one else had entered the theater the entire time any of this was happening and I was extremely worried someone would step in right then. There I was in just a bra and panties looking backwards (which is where the entrance was). If anyone stepped in, I would be unbelievably embarrassed. Jack looked me up and down and just said "Wow...Sexy," and gave me a big grin. He slowly stood up and grabbed me around the waist and gave me a huge kiss on the lips. I had never kissed a guy before and it was SO different than kissing a girl. It was rougher and more forceful, but incredibly sexy. I wouldn't quite say I "melted" in his arms/lips like it always says in those romance novels, but it did make me feel incredibly turned on and sexy. We kissed for bit and he caressed me all over, spending a bit of time feeling my breasts. I don't quite have big or female-shaped breasts naturally, but the push-up bra somewhat made my breasts seem feminine, so I understood why he liked them. After grabbing my ass one time, he pulled the thin piece of fabric between my ass to the side and stuck his finger in my ass. I immediately knew where this might be going and I was a bit nervous, but right then, I was in heaven. His lips, his hands, his finger in my ass, his body (though mostly clothed) against mine just felt amazing.
Over the next couple minutes, we kept kissing and he got up to three fingers up my ass. He might have tried four, but it wasn't the best angle and I think he was getting a bit horny. He let me go and stepped behind me and told me to bend over the seat. I was hesitant and said "I've never done anything like this before" and he responded "Don't worry, I'll be gentle and will take it slow." A bit of my conscience kicked in and I said "Wait, shouldn't you use a condom?" He said "Jessica, I promise you that I don't have anything. You don't have to worry. Do you trust me?" Oddly enough I did trust him and I never got anything from him, so I guess I could. I said "Yes daddy, I trust you." He slipped my shirt from the seat next to the one I was about to bend over to the one I did bend over. I didn't really understand why, but I didn't ask any questions.
I slowly bent over and spread my legs a bit. He spit on my ass hole. He then spit on his fingers and worked them into my ass. Then he spit all over his cock and rubbed it around. He ended up having to do this a few times, because unfortunately, spit is not the best lube and I was a tight virgin. He slowly lowered his cock to my hole and pushed in. It really did hurt, but getting the head through was the worst part. After that, it got a bit easier. He slowly pushed himself all the way into me. I was in terrible pain, but he just stopped and allowed me to get used to his manhood inside of me. He asked if I was alright and even though I was in much pain, I said "yes"...I just didn't want to disappoint him. He slowly started rocking a bit...not enough to move his cock much, but just enough to help me stretch out a bit more. As I said before, his cock was pretty thick, so my ass was an extremely tight fit for it, but it wasn't much thicker than my dildo back home AND it actually moved and compressed (like any cock would), at least more than the hard silicone of the dildo.
He pulled back, but not enough for the head of his cock to come out and he slowly went back in. He repeated this maybe a dozen times and after a while, I actually started to get used to it. He asked how I was doing and just responded "good." He picked up the pace a little, but was still very gentle. Eventually, I didn't really feel the pain and I really started to enjoy it. At very first, I may not have thought the actual physical feeling was great, but I was immensely turned on by the concept of being fucked. I was rock hard. He got up to a nice fucking pace and would even pull completely out sometimes and push it back in.
After a couple minutes of this, a man walked into the room. My heart started racing even more and I got incredibly nervous. It was dark, but once his eyes adjusted, he just stared at us. I couldn't really see Jack well, but I did quickly glance back and he just seemed to be pretending the other man wasn't even there, so I did my best to do the same. After maybe 30 seconds of watching us, he just left the room. I was a bit afraid he would go tell someone, but I was just more relieved he was gone. Jack fucked me for a couple minutes more and I was moaning and he would sometimes say things like "Oh! I love your tight pussy!" Then suddenly another man walked in and I had a similar reaction. But once this man understood what was happening, he slowly walked over to the other side of the isle and sat down. Jack just kept fucking. The man was probably in his early to mid-40's with short brown hair. He just stared and watched us, never once looking up to see what was on the screen. After a couple minutes, he pulled out his cock and started masturbating. I made eye contact and he gave me a big grin.
I couldn't believe what was happening. Just a few hours earlier, I was just a nice, quiet guy who sometimes liked to wear panties. But here I was in just a bra and thong (and socks) in an adult theater with an older man fucking me and another man jacking off while watching us. I was SO turned on and SO hard. I would have reached down and jacked myself off, but there was no good way to do it. After a few more minutes, Jack slowed his pace and pace and bent over me, pulled my cock out of the fabric (which wasn't very difficult, because the thong was already askew so Jack could stick his cock in me) and he started to stroke my cock as he fucked me. After just a couple of minutes, I came. It was the most amazing, glorious orgasm I had ever had. Remember, I had yet to cum, so it was all just stored up ready to come out. It lasted for almost a minute and there was SO much cum. It absolutely covered my t-shirt and I then understood why Jack put it there. If he hadn't, I probably would have ruined the seat. Once I finished, Jack just continued fucking me. He might have gone for 15, 20 minutes, I'm really not sure. But in that time, I really did learn to love his cock inside me.
Eventually, he really started speeding up and ramming his cock inside of me. It hurt, but it felt great and I knew how it made HIM feel. He started grunting and groaning and he sped up just a little more and suddenly he stopped pumping fast, but was still pumping hard. It almost seemed like work for him, but he was grunting like crazy. I soon noticed my ass seeming a big warmer and wetter and knew he had cum inside of me. Once he stopped, he just stood there for a minute and then slowly pulled his cock out. He slumped into the chair next to me and gazed into my eyes with a really sexy grin. I too sat down, but ended up sitting on my cum-covered t-shirt. But once I thought about it, it didn't seem like the end of the world considering I had an ass full of cum and wasn't sure if I'd be able to keep it all in. He leaned over and kissed me, rubbed my breast with his hand and said "You are amazing Jessica." I responded "No, you are daddy."
At some point the man watching us had cum and now, he slowly got up and walked out and didn't say a word, but gave me a nice smile. Jack and I just sat there for a couple of minutes. He eventually said "Jessica, would you like to come back to my place for a while? We can make love for hours and I will treat you like the amazing girl you are." Even though I was still very aroused (I had recovered from my orgasm), I was coming down off a hormone high and started sobering up. I said "I don't know Jack, I really need to get back on the road...my family is expecting me." I could tell he wasn't happy with my response, but he didn't protest too much.
He reached down and slid my pants over towards him. I had no idea what he was doing, but he gave me a big kiss, so I stopped worrying. He started to put his clothes on and said "Jessica, it's okay if you don't want to come home with me, but can you at least do one thing for daddy?" I said "Of course!" in a strangely high pitched voice. He said "Walk out with me holding my hand...with your bra on and no shirt." I gave small gasp and gave him a quizzical look. I started to protest, but he cut me off saying "Either do that or wear a shirt, but don't wear any pants. Would you rather show your thong or your bra?" I immediately answered "Well...bra, but..." He stopped me and said in a playful voice "Jessica, please! I won't give you back your keys unless you do it." He held up my keys and I realized that when he grabbed my pants, he also grabbed my keys "and" he continued "you don't want to wear that shirt anyways!" Of course, looking back, I could have mostly likely easily overpowered him and taken my keys back, but at the time I just felt helpless and said "...alright."
The cum started to come out of my ass...my sphincter was too stretched to hold it all in. The g-string soaked up some of it, but I knew there was a lot of cum. I had been worried that the cum would mix with "other things" in my ass, but as far as I could tell, the cum that came out was pretty clean. Jack noticed me examining my ass and said "Here, Jessy, I think you need a maxi pad" and handed me his handkerchief. I put it between my cheeks and used the g-string to help strap it in. It would at least help for a while. I put on my pants and my shoes and waited for Jack. He grabbed my t-shirt and slung it over his shoulder, but did so in a way that the cum wasn't really showing. He gave me a big kiss and reached down to hold my hand. We started walking out of the theater.
In the main lobby, there were SO many more people than when I came in. There had to be at least a dozen customers, two of them women (who came with men). They all turned and looked at us when we entered and all but three or so gave us (well...me) big grins. I was half really embarrassed, but I was also pretty turned on. I loved the fact that people got to see me in a bra...holding an older man's hand. I thought we would just quickly exit, but Jack started walking over to the porn...so what could I do? I just went with him still holding his hand. He acted like it was no big deal...like he just brought a regular, fully clothed woman into the shop. He started examining porn and I started to make eye contact with the guys around me who all gave me a big grin. One even whistled. One guy quickly passed and actually grabbed my ass. I couldn't believe this. They may not have seen me as "sexy," but a large group of people saw me as a sexual object! I was SO turned on. I slipped my hand out of and pulled his hand towards my ass. He slipped his hand in my back pocket and gave me a big smile. We walked all around the store examining things. We stopped at the lingerie and he asked what I thought. I responded "I love it ALL!" He gave me a big smile and we walked on. Eventually we stepped outside and walked to my car. I was extremely aroused right now and was actually sad to leave the store.
Jack pulled out my keys and handed them to me. I took them for a second and then grabbed him as tight as I could and kissed him. As I did so, I slipped my keys into his side pocket. When we finished, I said "I'm going home with you, daddy!" and he responded "I thought you would honey" and gave me a big smile. He then said "Okay, if you want, I will buy you ANY of that pretty clothing inside." I gasped "REALLY?!" and he nodded his head. We went back inside and started looking at the lingerie and costumes. We got even more stares as it was now even more evident that Jack was my "sugar daddy." I ended up picking out this really sexy pink bustier set with sexy panties and I also got some black pantyhose to go with it. Jack ended up suggesting that I get a maid's outfit so we could have some fun. I of course agreed to whatever he wanted, so we got both! I was so excited and both my heart and cock were pounding this whole time.
Jack wanted me to put on my new clothes while we were still in the store so we could let people have a look at me in my new outfit, but as we walked back to the video booths (so we could use one as a changing room), Jack stopped us and explained that before I put on my new clothes, he wanted to give me a chance to "clean up," so we started to head back to the door and on the way, he stopped me for a second and gave me a big, wet kiss.
We went back outside and Jack told me he didn't live far so we could just go in his car and we could pick mine up later. I was in no state to argue, so I readily agreed. After we got in the car, he asked me to slip off my pants and I did. So leaving my car, I rode off in my bra and panties with my new lover.
There is much more to this story, but I thought I'd go ahead and post the first part. If anyone really likes it or has any comments, please feel free to e-mail me at George3130@gmail.com.