A Con Goes Gets Conned by Bottomsup (MM, anal, 1st)

Happily stolen from http://www.asstr.org/~Kristen/45/sleeping.txt (Kirsten’s Archives, a great little collection).

A Con Goer Gets Conned… By Bottomsup (bottomsup@fastmail.us)

Anime conventions can sometimes have a real twist. (MM, 1st-gay-expr, anal)

I’ve been into Japanese Animation for years, starting back in college when I was a member of the campus anime club. I’ve always been fascinated by such incredible art, and the different perspective on things that the Japanese use. So I should have been ready for something strange when I went to this last convention.

I’d booked a room at the con this time instead of offsite. Offsite is nice for being discrete, but when the music’s pumping at 2 AM, and the drinks have been flowing all night, it really sucks to have to get a cab to your hotel. The parties tend to get loud and sloppy, since most of the people there are college age or below. I’m a little older than most, but since I’ve been an otaku for so long, everyone accepts me into even the youngest gatherings.

So, it’s 3 AM. The dance is starting to wind down, and I’m outside having a smoke. The wind is nasty, and it really sucks having to head outdoors in winter for a quick hit of nicotine, but what are you going to do. I’m sucking down the last of the cigarette, when out walks a vision. Now, I’ve been drinking pretty heavy all night, but even so, she was definitely worth a second look. Dressed in a sailor suit schoolgirl uniform, she bounced out the door and asked if I could give her a smoke. I pulled out my pack and lit one up for her, watching as she expertly sucked on the little round stick.

I didn’t know if I should try for her or not. After all, a lot of the girls here are definitely jailbait, and I’m to pretty to go to prison for 5 to 10. The cigarette isn’t a clue anymore because you never know these days, but then she pulled a beer out of her backpack, dropped to the railing, and started sucking on a cold one. Now, I know the only alcohol allowed in the place was from the hotel, and they insisted on having a real bartender and security. Not one of those half assed “security guards” that cons like to use, usually 15 year olds that are working for a free badge to the events, but real off duty sheriff deputies. So I figure I’m pretty safe, since she probably had her ID checked by at least 2 professionals tonight.

We start talking about anime, going over various favorites. Mostly she seems to like the YAOI stuff, like Fake, or Fruits Basket. I can take that stuff or leave it, I’ll watch or read anything once, but I’m more into GTO. I can understand a man that becomes a teacher so he can look up schoolgirl’s skirts. While we’re chatting she starts to shiver a little. Pitching my butt in the ashtray, I say, “Isn’t it a little chilly to be out here dressed like that?”

“I don’t have a lot of choice,” she replied, with a sexy little laugh. “After all, this sort of party is much more fun if you’re in full cosplay mode!”

This makes my heart skip a beat. Most of the girls I know that are into cosplay are also into just about everything else if you know what I mean. Casually, I asked, “Would you like to head up to my room? I’ve got a place here at the hotel. We can smoke there if we sit on the balcony, and I picked up something a little tastier than that crappy Budweiser you’re sucking on now. What do you say?”

She gave that little evil laugh again, and said, “Is that the only thing I’ll get to suck on if I head up to your room?”

At this point, my heart went into overdrive. I’m 29, and this girl was maybe 22 tops. She was definitely cuter than most, and we were into the same sort of things, or so I thought. I picked up her bag and held the door for her, gesturing for her to enter ahead of me. The lobby was pretty well cleared out, since most of the young ‘uns had gone to beddy bye already, and the older kids were up at the con suite, racking out for a little R&R. We quickly hopped on the elevator and took a ride to my floor. I was going to try to get a room right on the con floor, but I had figured I might not get any sleep if I pulled that, so instead I was 2 floors further up. We popped off the elevator and quickly made it to my room. I swiped open the door with my card and we quickly slipped into the room.

I like to be prepared, even though I hadn’t really expected anything much to happen tonight. I had already grabbed a bucket of ice, and I had a couple of bottles I had picked up at the liquor store sitting on the desk. One nice thing about the room I was in was that they included a full sized coffee pot in each room. I quickly started a pot brewing, and grabbed a couple of cups from the credenza. While the coffee brewed, I pull out everything I needed to make sure we had some fun. Bushmills whiskey, sugar, cream out of the minibar fridge, and a can of whip cream. Her eyes lighted a little when I pulled that out, but I laughed. “It’s for some Irish coffee honey. Nothing warms you up quite like it!”

I set about whipping us up a quick set of drinks, going heavy on the whiskey. After all, if she was planning on driving anywhere she wouldn’t have had the beer anyway. I handed her a mug, and sat down in the chair by the desk. She sprawled face down on the bed, her legs kicking at the air and a pillow under her breasts as she licked up some of the whip cream. All of this was driving me wild. I love the Japanese schoolgirl look, especially when she has beautiful red hair and huge green eyes that you could just sink into. The room came with a DVD player, so I pulled out one of my purchases from the con and slipped it into the player. “Tell me what you think of this one.” I asked her as I hit play.

The title was a hot little hentai number. The main character looked kind of like her, although I liked the one in the room better than the one on the screen. After all, this one was warm and slowly getting intoxicated. I sat down beside her on the bed and started working on her back, massaging her through the shirt. She purred, and snuggled into the pillow a little harder, as I worked down her taut back in to her ass and legs. Teasingly I ran my finger from her feet to her ass, feeling her thong panties under her skirt. She clenched her legs a little tighter, so I started to worry that I had gone too far, when she placed her empty mug on the bed beside her and grabbed my hand.

“Hmm…” she moaned, “I’ve always wanted to try that…” I glanced at the screen as the girl in the film was forced to take a huge cock in her ass. “Let me get you a little wet and see if we can do that!”

She pulled me in front of her, and pulled me closer to the bed. Using her finger, she scooped up a little bit of the left over whip cream from her cup as she undid my jeans. I never wear underwear, so my hard 8-incher sprang right out in front of her. She squealed, “Oh, what a big one it is!” and used the finger to trace the whip cream down my hard dick. The feel of her inch long nails running down my pecker was enough to make me almost come right there, but I really wanted to make this last. She stuck out her tongue and began to lick up and down my shaft, paying special attention to where the whip cream was quickly melting off. As she slopped on my dick, it was all I could do to stop myself from ramming it right down her fucking throat. This was one of my best fantasies, a hot schoolgirl uniformed chick sucking me off! I couldn’t believe this was happening, but I knew that more was yet to come.

Her nails tickled my dick and balls while she slurped on my tool, and I could feel the fingernails sliding around to my ass. I was going to be marked when this was over, but boy was it ever worth it. I even spread my legs slightly as she ran her nails lightly over the skin between my balls and my asshole, tickling me in a most erotic way. I pulled away and told her to sit up. When she did, I pulled her sailor suit tunic up over her beautiful breasts and buried my face in them. I loved the feel of the nipples against my face and tongue, and I really enjoyed the slight hint of muskiness from where they had been trapped during her partying at the dance.

I worked my way up her neck, biting and kissing my way to her mouth, where she immediately started probing for my tongue. As we dueled with our mouths she grabbed hold of my balls and gave a little tug. “I want you to fuck me in my ass. Just like in the movie. Fuck me up the ass, right under my skirt.” I reached down as though to tug off her little panties and she said, “No, leave them on. Just pull the thong aside and fuck me while I’m still wearing them. It will make me SO hot…”

Now I’m not a man to leave a woman in a desperate situation so I decided it was time to start quenching the fire this little girl obviously had in her little bottom. I placed her over the edge of the bed, with her cute little ass in the air. I got down behind her and began to lick and bite her ass cheeks. She giggled and shivered, but when I finally took my first lick at her gorgeous brown eye, she moaned. “Don’t play around, I need you!” she panted. As my tongue darted into her cute little ass like a hummingbird into a flower, she moan again. “Do it! Do me now! PLEASE!”

I placed the head of my slicked up dick at her tight little hole and started to shove. The angle was almost right, but not quite, so I slide the pillow down under her hips, raising her slightly. Now it was perfect. I started to slide into her ass. It was like a pussy at full ripeness. Obviously this wasn’t the first time someone had been up there and I was sure I wouldn’t be the last, but it was still tight and hot and moist.

No matter how used an asshole has been, it’s always going to be tighter and hotter than any pussy can ever be. I mean, don’t get me wrong, I like fucking a girl regular too, but using her ass I can feel every ripple in her tight dark channel as my dick works its way up her chute. I started working my way up, stopping when she tensed up a little at the half way mark. “It’s so big…” she sighed, with that fluttery little catch in her voice. “I don’t know if I can take it all!”

“Well, we’re gonna find out sweetheart, cause I don’t plan on pulling out now!” And with that, I continued plunging into her abyss. Soon I felt the skin of her ass against my crotch. I shave because I love the feeling of that skin to skin contact when you’re fully inside her. I started to pump, slowly at first, a little at a time. I would pull out a little then plunge right back in. Then I started pulling out further, leaving just the head inside until she begged me to ram it home. In and out I plunged into that hot little ass.

The whole scene was made even more lewd by the sailor skirt thrown up over her ass cheeks, the thong scraping along the edge of my dick each time I pulled out. I couldn’t believe how hot this had gotten me. I’ve never had anything quite like this, I thought, and made a mental note to make sure to pre-register for next years convention. I leaned over her back, on my elbows, pulling at her tits crushed under her body, biting her neck and ears. “I’m fucking you. I’m fucking you. I’m fucking you like I’ve never fucked anyone before. My god you’re hot. I love the feel of your ass against my body. I love the feel of your hot little asshole. Can you make me come? Can you bitch?”

As I said this I felt her start to clench and relax her anal muscles, milking my cock like an automated milking machine works on a cow. I groaned in her ear, thrusting harder and harder up her tight little ass. “I’m going to cum up your ass bitch. How do you like that? I’m going to paint your insides with my cum. Are you ready for it bitch? Are you ready?”

“Oh god yes! YES! YES!” she screamed, as my boiling load started screaming up my cum tube. “Cum in my ass! Cum in my hot little schoolgirl ass!” That was all it took. I started blowing wads of scum up her chute as I rammed myself repeated balls deep into her ass. I even managed to keep going for a while, because I was still hard even after coming. After a couple of more thrusts, I felt a deep tearing sensation in my groin as I delivered up the last of my pearly white cum.

I fell forward onto the bed and still lodged in her asshole I rolled over, putting her on top of me. She sat up, trying to keep me captured in her ass. I sat up and grabbed her tits from behind, roughly working them in my hands as I pulled her back down onto me. I rolled her over into a spoon, and cuddled up behind her, still inside her as we slowly stopped panting after our cum.

The alcohol and the adrenaline rush finally caught up to us, and I started to drop off to sleep, holding her in my arms.

About an hour later, I started wake up a little bit as I felt her licking my cock and balls. I was still exhausted from the last time, as I don’t know when I had last cum that hard, so I just laid there and enjoyed the sensation as she licked and sucked her way from the top of my cock to the base of my balls. I felt her playing with my back door, and shifted my legs slightly to give her room. If she was able to get me jump started again, I didn’t care how she went about it. I was rewarded with the feeling of a finger entering my own hidden hole.

I’d done this before of course. Who hadn’t? When you’re not 18 anymore, you need to know the tricks if you want to get back up again in a hurry. So I relaxed as her warm spit covered fingers played with my anal opening, first one finger then another working it’s way up my brown eye, as she used them expertly to play with my prostate. I could feel my body starting to respond to the expert technique, and sighed as she pulled her mouth away with a lewd little string of spit connecting her lips to my dick. Still playing with my ass, she worked her way up my body and began planting a kiss on my mouth.

I felt the fabric of her skirt bunching up between us as her fingers probed more and more expertly in my anal passage. Then I felt an emptiness as she removed her fingers and kissed me harder than ever. I felt something knocking at my back door, and then realized that it wasn’t a finger any more. My eyes got wide as I felt her hard cock enter my virgin ass, pushing hard through the sphincter holding it closed. The chick had a dick! I could not believe this, but as she held my arms to the bed and forced her way into my ass, I realized that I didn’t have a choice but to believe it!

At first I was shocked and confused. I am not gay, and have never had anything but a finger up my ass. I couldn’t believe this was happening to me! But as the pain passed, the hardness of my cock bunched into her skirt was enough to let me know that no matter what I had thought in the past, I really was enjoying this. As she realized I was no longer fighting it, she quickly took my hands and placed them on her tits, I quickly started playing with her hard nipples as I felt waves pleasure roll through my body.

Each thrust of her 6 inch tool rode over my prostate, making my dick harder and harder. I felt wanton, playing with these gorgeous tits while getting plowed up the ass by a hot thick dick. As I felt her start to cum up my ass, my own hard boiled cock suddenly started spurting cum between us, all over her skirt, and I pulled her down to me and kissed her hard on the mouth. As soon as she came, I could feel her slipping out. I tried to hold her in, but I wasn’t used to this, so she slipped right out of my hard used ass.

She stood up, and the skirt dropped down again. And there she was, again a beautiful woman, wanting to be used. I sat up and we lit up a couple of cigarettes and talked about it. She told me that she never did this sort of thing, that she was actually fully in character the whole time she was here.

This was the first time she had ever slipped like this, and she hoped that I wouldn’t give away her secret. Like I could, since then everyone would know I had been fucked up the ass by this beautiful woman. I told her that this was a first for me all around. We sat and had a quick nightcap, then she kissed me again and said she would see me later. With a wink, she disappeared from the hotel room. I took a shower and hit the bed exhausted and needing to be at the con early the next day, I quickly fell asleep.

She came back the next night and we tried even more. I still can’t believe that this happened to me. But next year, we’re talking about sharing a hotel room at the con, so we don’t have to sneak her into my room. END