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Fun stories #5  

DJpaddock20 44M
31 posts
8/19/2009 2:06 pm
Fun stories #5

Shemales, shemales, shemales, who doesn't love them. Best of both worlds really. Great body, nice boobs, nice hard cock. Obviously, a true shemale is the best thing people hope for, but there are tons of transvestites and cross dressers out there that work it very very well and can definitely fill the bill, and an ass.

It'd been a few months since I'd gotten back from that Med cruise I talked about in my last story. New apartment but the same roommate, so everything was cool. He knew I was bisexual, and knew I had people over all the time. He didn't care as long as he didn't actually see anything. He'd just go downstairs and turn up the TV or something. Anyway, I'd been with around a hundred people so far in my life, but only guys and girls. No shemales, or even cross dressers. I decided to make it my top priority to find a hot gurl that was at least versatile. I'm all for fucking a shemale or cute crossdresser in the ass, but I'd much rather get fucked first .

After almost 2 months of searching, finding, and talking to a few gurls in the area, I finally found a shemale that wasn't a fake, a flake, or crazy and addicted to drugs. (I'm not saying they're all like that, just most of the ones that were on AOL in the VA Beach area back in 2000 were . I've met many wonderful gurls since then.) As luck would have it, she was a nice thick black gurl, with a nice fat uncut cock. Little over 7" long and almost 2" thick, right around 5'9" or so, and pleasantly thick. Big fat ass and great tits. Not as hot as the gurl in the picture up above, but close. After almost a month of talking back and forth, and 3 missed connections, our schedules finally matched up and we both had a night free. What a night that became.

She came over a little after 7pm and we sat and talked for a little bit. My roommmate was on duty that night, so there was no chance of us being disturbed by anything or anyone. Very smart and articulate. If she'd been interested in something more serious than a friend with benefits situation, there would have been a good chance of us staying together for a long time. We had a lot in common, sexually and non-sexually, but like all hook up meetings, the conversation turned toward the sexual fairly quickly. I was wearing what I called my peek-a-boo shorts, they were an older pair of jean shorts that had just worn through in the crotch, so I'd cut them a bit more so you could see everything, depending on how I sat. Every so often my dick or balls would peek out, when I got up to change the movie in the DVD player, I made sure that she got a good view of my asshole. She was playing the same game with me too. Knee high white boots went up along with thigh high white<b> fishnets </font></b>to a very dark red one piece that was definitely a few inches too short. She wasn't wearing panties, and I could see her cock and balls a lot, every so often the tip of her dick would peek out below the level of the skirt. The upper portion covered most of her midriff, with a keyhole going from the bottom of her tits to her waistline. It was totally backless as well, and she filled it out gorgeously. Very hot and very sexy. It didn't hurt that she kept crossing and uncrossing her legs, and laughing, which made things move very interestingly under her dress.

I asked her if she wanted to go upstairs, or if we should just make a mess of the living room. She said that she wanted a shower, she didn't have time to give herself a good cleaning inside and out before she left. I led her upstairs and we got undressed fairly quickly and started making out while the water heated. She was a *very* good kisser, and both of our cocks were rock hard and leaking pre-cum everywhere. She hopped in and started washing herself while I got a few things ready to help clean out her asshole. I still don't know what she was worried about, the water came out perfectly clear and clean smelling from the beginning, but I bet she liked it being done by someone else. I know I sure do, especially if they're good at it. We stayed in the shower for a good long while, fingering and stroking each other, and making out a lot. After a good 30 minutes the hot water finally ran out and chased us out of the shower. Then the real fun started.

I have this toy that is a combination vibrator and cock ring/cage. It slips in your ass and stays there, and has a latex cage thing that goes around your whole package, and your dick as well. It's all about making your dick harder, and making you cum harder. I showed it to her and her eyes lit up like nothing else. She got down on her knees and was sucking my dick, and looked up at me with her big brown eyes and asked very nicely if I could fit that in and on her. I don't remember picking her up and spinning her around in mid-air, but I must have, because she was suddenly on the bed doggiestyle in front of me. The cock ring and cage stretched pretty far getting around her package, but everything was situated, and she said that she immediately felt her cock grow due to the rings. I gave the vibrator end a good lubing and eased it into her pulsating asshole until it was locked into place. I turned it on the lowest possible vibration setting, and her cock spasmed and started dripping pre-cum at an alarming rate. I almost didn't get my mouth around it in time to drink it all. I took her gorgeous cock down my throat to the hilt and started licking her balls. About 10 seconds later she moved back and grabbed my head and pulled me off her. I could see why, she was leaking more than pre-cum and somehow she stopped her orgasm. I was a little disappointed, but she pushed me on the bed and told me to get on all fours and get the fuck on her dick. I wiggled back until my ass was touching her stomach, she pulled back and gave my asshole a good licking to lube me up, then rammed her very very hard cock as far as it would go into my ass. She grabbed my hair and pulled back, started fucking me as hard as she could. Lasted all of about 30 seconds then spurt after spurt of hot cum sprayed into my ass. She stayed quivering inside of me for about a minute, then I pulled forward and sucked her now shrinking cock clean. She waited until I was done, then shoved me back on the bed again and ordered me to give her cum back. She helped me by sticking a finger or two into my ass and sucking it all out, then climbed up me and started kissing me and sharing her cum and my juices.

After we lay there for a few minutes, she grabbed my dick and told me she felt bad because I hadn't gotten off yet. I told her she should do something about that, so she did. She stood up a bit and straddled me, then pulled the vibrator out of her ass with a very loud pop, and sat back down, enveloping my cock with her very hot and quivery asshole. She asked me if that felt good, and as I was moaning "fuck yeah it does" she shoved the vibrator in my mouth, which just made me even hornier. She was holding me down very well, legs on my legs, hands on my hands, and slowly riding and grinding my cock. She also wouldn't let me spit out the vibrator either, so I was tasting what my dick was tasting at the same time. She was very very very good at it too. She would feel me begin to swell just before cumming and stop moving. She did that one two many times, and just the feeling of being inside her, and seeing her fat cock and balls on my stomach started an unstoppable reaction. She felt it and started moving very very fast, bouncing her ass on my balls, her balls and cock on my stomach, her tits jiggling up and down, all while I was cumming harder than I had in a long long time. I thought it was never going to end, I didn't want it to end. I wanted her to ride me forever, and I wanted to cum forever. She finally stopped moving, and I finally stopped cumming, and we just lay together for a minute, me still inside her. I asked her if she wanted me to clean her out, she said I'd better or she wouldn't fuck me again. What was I to do but suck my cum out of her asshole while she sucked me clean. When I'd gotten it all out we kissed and shared my cum and her juices.

We lay on the bed for an hour or so, talking and caressing and kissing and licking. I noticed she was getting hard again, so I started sucking her very rapidly hardening cock. She grabbed my head and started face fucking me, slamming her cock deep into my throat with every thrust. She kept that up for a few minutes, then told me to get on my back. She spit on her dick to get it nice and lubed, then slowly pushed it into my ass inch by glorious inch. She was slowly fucking me, and kept giggling every time she hit my prostate and made my dick jump, which would make her breasts bounce, which would make my dick even harder, and jump more. It was a very fun vicious cycle . I think she fucked me slowly like that for a good hour, then started speeding up, her cock hitting and massaging my prostate more and more. She kept it up until I started cumming from just the prostate massage alone, then she grabbed my dick and started jerking me off onto my chest. I'd never felt pleasure like that before, and my ass started spasming like crazy. She kept fucking me faster and faster, and harder and harder, full long strokes deep into my ass. After a few minutes of this, and long after I'd finished cumming, she sped up even more and then slammed herself as far into me as she could. I could feel the head of her dick swelling to monstrous size inside of me as she splattered my insides with her hot cum. This time there was no staying inside of me for any longer than a minute or so. My ass was still spasming from my orgasm earlier, and from the hardcore fucking I'd just gotten. That didn't bother me, I sucked her very clean, and she sucked her cum out of my asshole again, and then we shared it once again.

We were both very spent after that, and fell asleep together. I woke her up the next morning earlier than I'm sure she'd planned for and we had another amazing session like the night before. Not only was she totally amazing in bed, and had great tasting cum, but she was an amazing person. We just lay there afterwards until she had to leave to get ready for work. I met up with her several more times until she moved to Dallas, and every single time was as awesome and load blowing as the first.


bicouple4bisex 60M/73F

11/16/2009 10:22 pm

WOW!!!!


DJpaddock20 44M
264 posts
11/17/2009 6:35 pm

That was my general thinking for a month or two afterwards .


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