First Night Out

((Note, sorry if my story writing comes into the story, got to admit, though, it is one amazing journal entry!!!))

Okay. Last night was weird. It was Halloween night at Spiders, as you all know. And those that went also know that I went with Shel, in a dress…

First she waxed me, around dinnertime, and that stung like hell. But I should be hairless for a while. Then she chose the clothes for me. I chose hers so it was a fair trade I suppose. First she stuck me in a red corset, with fishnet stockings and a black thong (I had to end up sticking my dick between my legs… hurt a little but did the trick of hiding a bulge). She filled out the breasts with some fakes we bought a while back. Then she put on this tight dress, which went down to my knees, but had a slit all the way up the side of my leg. The breasts were exposed at the top, but covered my arms. Down the back was lace holding both sides together. Lastly were 5” high heels, with straps running around my shin. I could barely walk in them, and made me tower over Shel.

Then she did my makeup, foundation to cover my beard shadow and the blackness under my eyes. Blue and purple eye shadow, mascara (and she used eye lash curlers… owwy, I don’t wanna be a girl…), eyeliner, and some deep red lipstick. Black varnish covered anything that was considered a nail. The last touch was my hair got braided back onto itself, so the ends came to the front. Basically, waxing me took an hour (it was my entire body), getting dressed took half an hour, and makeup took another hour!

And Shel was getting ready at the same time as me. She didn’t need to wax, just a quick shave. She had finished in a thong and suspenders holding up fishnets. A dress with a slit in the middle (it goes between the legs, up to the top ;)) went over the top. The top half was PVC, and cut short. It clung to her breasts well; squeezing them together and pushing them up, making them look larger. She was in similar shoes to me, but I had put her in 6” heels, making walking even harder for her who was also used to 3”. Her makeup was the same as mine, but with green eye shadow, not blue, and purple nails.

Once we had finished preparing, we stood in front of my mum’s full-length mirror. I nearly fainted, but instead turned and kissed Shel passionately. She pushed me away a little after kissing back, and re-applied the lipstick. For once, though, I felt I had the confidence to go outside.

Slowly we walked down the stairs, and went into the living room. I went first, and did my mum a little twirl. Her mouth was wide open when she heard me speak. She though it was Shel, not me. Must have been quiet a shock. Who thought I could brush up so well? Shel came down and my mum just smiled at her. We stepped out into the night, and into my mum’s car. My now tall 6’6 figure barely slinked into the car. Shel’s 5’9 figure fit quite easily. My mum had a go at us as usual though as I told her to drop us off at the top of the street. She couldn’t understand that we needed the walking practice. Though Shel thought it was funny I wiggled my hips…

We go to the entrance. Ahead, I could see Mark, Gareth, Iain (who said was not going to go again…) and a few other hundred of my friends. None of them knew Shel, not really, and I didn’t want to greet them right now. So we hung around at the back. After 20 minutes, the whole time getting chatted up by 2 blokes (I faked a girls voice, which apparently should of won me an Oscar! Thanks Shel!), we got to the front door. Just as I was going to say something, the one which had ‘claimed’ me jumped ahead and paid us all in. They took us to the bar, and we got drinks paid for nothing too. Then we ditched them and wandered over to the cages.

All my mates hung out there, and were quite shocked, but happy, when I sat down next to Mark. He jumped out his skin when he realised it was me (he pinched my ass, cheeky bugger).

Afterwards, around midnight, we were sat on some plastic chairs. Shel was on my lap, with the slit on her dress covering my legs. She sat on my hand, as it caressed her ‘lips’ gently. It was so wet. The entire thong was soaking. She bent down and whispered into my ear about fucking me. I stood up, and twisted the dress a little. But before I could untwine my dick from my thong, she asked to leave. She couldn’t do it in the club, and wanted to surprise me at home.

We left, tripping a little, but both hot even in the cold night. We quickly waddled to the back of spiders, and she pushed me forcefully against the wall, biting at my neck and kisses me deeply.

After what seemed like an eternity of pleasure, a grunt came from behind her. I opened my eyes and stared at two guys standing there, some cash in there hands. Shel turned around slowly, and glanced down at the cash for a second. She told them that we were not prostitutes, but then they said that all they wanted was blowjobs. All they could afford. They only had £75 each.

Shel turned to me and talked me into it somehow. She must have used puppy dog eyes or something. In the end, we both knelt down, holding each others hands, and undid their trousers. My guy had a largish cock, larger then mine. I didn’t glance across, and felt a little sick doing it. Now I don’t think I would mind doing it again… and I mean that… But at the time…

Slowly I slid my tongue over his end. I knew it would get him, it gets me. I just concentrated on what would have been good for me. After about 2 or 3 minutes, he grunted and cum. Of course they had condoms on, so I didn’t have to swallow the taste. That’s also something I wouldn’t mind knowing about…

Shel’s guy took longer. I just stood up and started whispering things into the guy’s ear, running my sharp nails along his neck and constantly threatening to bite. I just wanted out of there, we had the cash. But on the other hand, they looked like they could outrun us, especially because were in high heels.

Suddenly I felt a hand on my thigh. I turned around at my guy, and bluntly told him I was anal only for guys. He didn’t seem to care, and started running his finger against my arsehole. That really shit me up; I could feel his finger inches from my dick. And I don’t think he would have been happy if he found out I was a guy… So I bit hard on Shel’s guy’s neck. He came almost instantaneously. We then got paid, and wandered home, half drunk and still very, very horny.

We got in, and I slummed onto the bed. I was really tired, and was not expecting the walk to do that to my legs. Slowly Shel took her shoes off, and then went into the bathroom at the end of the hall. I heard the toilet flushed, then turned over and rested on my chest, smiling.

Then she pushed my dress up. I lifted up my body, expecting her to take it off my back, but she never. I felt her finger; already lubed up, push itself quickly into my anus. I shivered and turned to ask her what she was doing, when she removed it and pushed the dildo deep into my ass. I instantly sagged and screamed into the pillow. But it wasn’t in pain. My sharp nails dug themselves into her bottom, as she groaned too. I knew what she was wearing; it was a little joke for Heather. I had bought a lesbians strap on, dildo on both ends of a pair of underwear.

I couldn’t help but scream, and so was she, as she gently pushed it in and out of me. Somewhere, I turned over, while she kept up the steady rhythm. But then it stopped. She pulled the dildo out, and smiled at me weakly. Slowly she stood and took it off, then fell to her knees, smiling like I had done something wrong. I pounced on her and pushed my dick deep into her. She was still soaking, so my dick slid in quickly. I kept pushing in deeper, groaning at the thoughts running through my head. I couldn’t get the dildo out from within me, so it was not me pushing on her; it was me landing on her.

Afterwards, must have been ages, the sun was rising up. We lay in bed, half asleep. No longer dressed (no longer dresses…).

After about 20 minutes of sunlight, I got up and wrote this. My feelings about the dildo are still vague. Hell my feelings about the entire night are vague… But I would defiantly do it again, especially if I come off £50 richer!