• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • A Night Out To Remember Ch. 02

A Night Out To Remember Ch. 02

The next part of my little story I hope you like it...

Decisions... decisions... we all make decisions everyday and most of them are simple easy decisions. Some may take hours, some take seconds and some are made before we even know it. Some decisions carefully planned and some have planning at all. Some decisions are between several choices and some are a simple yes or no. Some decisions are small and change nothing while others will change everything.

The decision to go to Liz and Sue's anniversary night-out was an easy decision that had lots of planning. The decision to go dressed as a woman was more of a yes or no and the planning was all Liz. The decision to allow Garry to chat me up was one that I didn't realise I had made until it was too late. The decision to kiss him while dancing was made before it happened and felt natural. The decision, to suck his cock in the middle of the gent's toilet, was all mine and only took a second to make. The decision not to get into the taxi with him was the hardest I had made all day.

I wanted to do it but the blowjob in the toilet had satisfied my lust just enough for reality to kick in. I was staying at Liz and Sue's house and he was staying on his sister's couch. I wasn't dressed for a long walk home if he kicked me out once he found out my secret. I wasn't dressed for the journey back to Liz and Sue's house even if he didn't. There were just too many things that could go wrong to take the chance of getting into that taxi.

It was late and everyone was getting ready to go. We danced one last dance and the goodnight kiss was a long passionate kiss that had his cock pressed against my belly for a second time. I reluctantly got into the taxi with Liz and Sue and we drove quietly back to their house. Once there, Liz was excited and full of questions.

"What were you thinking? What did you do? What did he do? Did you enjoy dancing with him? Did he try to kiss you? Was he a good kisser? What did you do when he kissed you? Where did you go after your dance? What did you do after that? Did he have a big cock?" The questions just kept tumbling out of her mouth.

I have known Liz for a long time and we have shared so many secrets that it seemed only natural to tell them what happened. For every answer I gave Liz or Sue, they had another two questions. They wanted more detail and asked how I felt when he wanted to do something and when I decided to let him do it, what it felt like when he did it. We were all to excited to sleep so Liz grabbed a few bottles of beer out of the fridge and settled down to hear the whole story again. I didn't mind as I wanted to savour every detail while it was still fresh in my mind.

Half way through the second or third retelling it was obvious that everyone was really starting to get turned on. Sue suddenly said she had something to do and would be back in a minute. A minute was more like 15 and when she came back it was easy to why it had taken so long. She was dressed in a nice pale blue suit, a man's suit!

"What the fuck is that?" I spluttered, "Why didn't you tell me you had that? Why did you make me go out dressed like this?" I suddenly realised that I was still dressed in my sexy dress, panties and bra. I had been so excited by tonight's events that I had forgotten to change and then I realised I didn't want to change anyway. If the night had been a disaster I think I would have been furious but the night hadn't been a disaster, in fact, it had been a bigger success than I could have imagined. I was still a little annoyed but the dress felt so good and I had really enjoyed my night out.

"I'm sorry, I had forgotten we had this. We only use it for special occasions and didn't think of it once Liz had her good idea." Sue explained "besides it looked like you were quite happy to dress up."

"OK I forgive you but why put it on now?" I asked confused but now very interested in why he had decided to wear it.

"Well now that you have learnt how to dress as a woman, I thought you might want to learn how to fuck like a woman too." I heard a squeal of delight from the chair next to me. Liz knew what was going to happen next but I was confused. "Don't worry, Liz will show you how to do it."

Liz squealed again and stood up to show me how. She walked over until she was standing between me and the very manly shape of Sue. "First you have to take your clothes off but not too fast or too many to begin with. You don't want to spoil the surprise." Sue continued as Liz started to take off the tight white camisole she had been wearing. She slowly lifted it up and then over her head. Her gorgeous tits bounced into view, barely contained in the soft lace bra. The nipples were trying to drill holes in the thin fabric as it strained to hold her excitement. Then she slowly turned to face away from me. She undid the waistband of her dress and slid the zip down. She hooked her thumbs into the top of her dress and pushed it down, bending at the waist. I was treated to the sight of smooth round ass as the dress moved down her legs. When her hands reached her ankles she stopped so I could take a long look at her sweet cheeks and obviously soaking wet crotch of her panties. She stepped out of the dress without standing up and slid her hands up the inside of her legs until she reached her wet pussy. One finger slowly rubbed the warm crotch of her thong before she turned and sucked the finger for me to see.

Sue was clearly pleased with Liz's performance as she was rubbing her own tits through the thin shirt she was wearing.

"Very good, now it's your turn. Just copy what Liz did." She told me and I got up. "Don't face her, face me." Sue said as I turned towards Liz. Standing in front of Sue, I took hold of the hem of the little camisole and slowly pulled it up. Getting it over the fake boobs that were tightly held in the pale blue lace bra was difficult and I'm sure I didn't look sexy but Sue smile reassuringly as I finally pulled it over my head. I looked down at the lace cups and could see the nipples poking out at the front. They were not as hard as Liz's but that was because they were made of silicon. At that moment I envied Liz more than I could have thought possible. Underneath the silicon my nipples were rock hard but no-one could see. I ran my fingers over the rubber nipples and tried to imagine how good it would be to have real tits.

"Now the dress, remember to really show me your nice tight ass as you do it." Sue said as I was getting distracted by my tits. I turned and copied Liz as best as I could. The feeling of the dress as it pulled gently over the nylon of my stockings was unbelievable. It was like electricity playing across the surface of my freshly shaved skin. When I reached my ankles I could feel Sue's gaze on my ass and I loved it. I felt sexier than ever and knowing she could see the cum stains on the crotch made me incredibly horny. I rubbed my finger over my puckered asshole before standing and sucking my finger like Liz.

"Very good, but we will need to shave your virgin ass before Garry sees it." I hadn't thought about shaving that part of my body as I didn't think anyone would see it. Now I really wanted Garry to see it. "OK, now you are ready to undress him." I looked across to where Liz was sitting and she was slowly fucking herself through the taut material of her thong. She almost leapt up when she realised it was her turn again.

She positioned her self in front of Sue but in a way I could see what she was doing. She carefully undid each of the buttons of Sue's suit jacket before pushing it off her shoulders. Next was the shirt, Liz pushed open the front and slid her hands inside to rub Sue's pert tits as she pushed the shirt off. She kissed her way down the front of Sue's chest before reaching the waistband of her pants. The zip was first and the sound of it sliding down sent shivers down my spine, all the way to my crotch. Liz unhooked the waistband and pulled them down. I was surprised to see a bulge in the bright red boxer shorts that Sue was wearing underneath. Liz finished with the pants and lifted her head back up to Sue's crotch. They turned slightly so I could see what happened next. Liz pulled the front of the boxers forward and then down to reveal and huge thick plastic cock. Liz licked the head as soon as she saw it and continued to lick every inch of it as it was uncovered. Soon the whole of the dildo was being licked by Liz's eager tongue. She licked from the balls to the tip before plunging the whole thing into her mouth. She grabbed the base of the plastic cock with one hand and started to wank it as she sucked as much of it as she could down the back of her throat. There must have been something on the inside of the harness as Sue was getting really hot as Liz pumped her hand up and down the length of the cock in her mouth. I could see Liz's other hand was down between her legs as she frantically fingered herself.

Sue started to fuck Liz's mouth with the same uncontrolled lust and soon the two of them came with an explosion on screams and moans. Sue almost knocked Liz's teeth out with the violence of her orgasm. I just stood watching as my thoughts of the blowjob I gave Garry came flooding back. I wanted to give him the same shattering orgasm that Liz had just given Sue.

When Liz finally came down from whatever cloud she got to during her orgasm, it was my turn to perform for Sue. She redressed herself and I slowly undressed her again. I copied Liz as best as I could although there wasn't the same passion as there was between her and Sue. Sue did help as much as she could and even Liz came over to help, telling me when to pull and when to suck to get the best effect. As I pulled and sucked, I could hear the dildo inside Sue's cunt as it slid up and down her sopping wet tunnel. I did manage to make Sue cum but it wasn't as explosive. We decided to rest for a minute before the next stage. I knew what the next stage would be and was very reluctant to wait but Sue's cunt was still throbbing after cumming twice in just a few minutes.

Finally Sue said, "OK, now we will show how a girl fucks!" Liz was more than ready for this and was bent over in front of Sue before she could finish the sentence. "Try not to be too eager." Sue said to me as she slapped Liz's offered ass. "You don't want him to think you are a slut." She said as she dipped a finger into Liz's cunt.

"Bitch! That's the last time I let you be the man." Liz scolded in mock indignation.

"Quiet, or I won't demonstrate on you first. I'll fuck her and you can go to bed." Sue giggled.

"Stop messing about! I want you to fuck me with your big hard cock." I almost shouted as things were getting a little off track.

"She wants me to fuck her with my big hard cock." Sue teased. "Shall we show her how it's done first?" Sue rubbed the head of her strap-on over Liz's panty covered crack before pulling the crotch to one side. Again she rubbed the head along Liz's crack. I could see it was already wet from Liz's juices. Back and forth over the throbbing cunt, along the swollen lips and onto the sensitive nub of Liz's clit, Sue worked Liz into a frenzy before plunging the whole of the huge plastic cock into Liz's hungry slit. Liz came instantly and her whole body shook from the intensity of it. Sue waited just long enough for Liz the stop shaking before she started pounding her cunt with powerful thrusts. Liz moaned with lust as she tried to push herself, back onto the plastic cock. She came over and over again until Sue slowly pulled the dildo from her dripping cunt.

"I think because she doesn't have a nice wet cunt like yours to fuck, I will have to show her how a girl takes it up the ass too." Sue whispered quietly to Liz as she ran her finger along Liz's juicy cunt and then spread her cum over the puckered anus that was just above it. The dildo disappeared into Liz's asshole easily and soon they had built up a rhythm and were fucking with the same force as before. Liz screamed again and went limp from the force of her orgasm.

Sue turned to me with a wicked grin on her face and said, "Now it's your turn. Bring your tight virgin asshole over here where I can make your fanny-assed dreams come true." She stroked the hard cock as she waited for me to reach her. "You better have something to hold on to. I wouldn't want to knock you over when I shove my big cock in your sweet ass and start to ram it in and out as I know you want me to. I was gentle with her but I'm going to fuck you hard!" Sue hissed as she pointed at the table near the window. Instead of feeling scared I wanted her to fuck me as hard as she could. I wanted her to rip my ass open. I wanted her to stick that big fat plastic cock in my ass and take my cherry.

I grabbed the edge of the table but Sue told me to lay my chest on it and to stick my ass in the air. It felt strange having the fake tits between me and the table but some how it felt right. I should have my tits pressed onto the table if I was a real girl. My ass should be ready to take a big cock whenever my lover wanted to fuck me.

Sue stood behind me and almost ripped my panties down. The cold air hit my ready and willing asshole. Sue shouted over to Liz who was recovering from her fucking. "Come here honey, I need some lube from your gorgeous cunt." She came and laid across the table next to me. "On your back so she can suck your tits as I fuck her." Sue said as she gently helped her lover turn. Liz stripped off her bra and her nipples begged to be sucked so I pulled the nearest one into my mouth and gently suck it. Sue pulled Liz's drenched panties down over her legs and gave her exposed lips a kiss. "If you are a good girl I might let you lick her cunt too."

Sue slid the head of her cock over the dripping snatch just inches from my waiting ass. When it was ready she wiped it over my anus. I wanted it so badly that I almost pushed myself back onto it. "Wait, don't rush it. I want to savour taking your cherry." She stroked my pouting butt-hole with the head a little more to make sure was well lubricated and then stopped with it resting at the entrance. I waited and waited, willing her to push it in. She seemed to be torturing me with it and then she gently started to push. At first it didn't move but as the pressure increased it inched forward a fraction then my ass started to open up. It was an incredible feeling as it slowly stretched the muscles that normally only let things out but now were letting her push the huge dildo in.

I thought it was going to split me in half until the head pushed past the last barrier and suddenly it slipped all the way to the fake balls. I came with a bang that nearly blew my balls off. My cock had been hanging between my legs and I could feel the hot cum splashing on my thighs. My anus pulsed around the dildo up my ass. I moaned as the feeling subsided, I wanted more and as if Sue could hear more thoughts she began to pull her cock out. I was just about to tell her to stop when she pushed again. Deeper and deeper it went with every stroke. Soon Sue wasn't just pushing in and out but actually fucking me and she was fucking me hard. I sucked hard on Liz's tits as Sue pounded my ass. The three of us locked in a frenzied fuck, every thrust pushed Liz's nipple into my mouth. Every time Sue pulled back I would push my ass back to keep it from slipping from my hungry ass. I was so turned on that Sue stopped moving and I fucked her cock with my ass.

Liz decided it wasn't comfortable on the table so we moved to the couch. I draped myself over the arm and Sue told me to turn on to my back. She pulled the lace panties off before lifting my legs over her shoulders.

"I want to see your cock when you cum over your lovely round tits." She said as she lined up the dildo with my stretched hole. I looked down to where she was standing and saw the huge cock standing straight up between my tits. One shove and it was deep in my ass again but this time I could see it going in. I felt more alive than ever and wanted it to last all night when Liz climbed onto the couch and lowered her sweet smelling cunt onto my waiting tongue. This time Sue's frantic fucking simply forced my tongue along Liz's gaping cunt. I thought I would drown in her sweet tasting juices until she was wracked by a huge orgasm. This was enough to make me spray the underside of my tits with cum. A moment later Sue came, ramming the hot plastic cock even further up my sore ass.

It was now very late and we were all completely knackered and so we decided to go to bed. We quickly showered together and Liz found a delicate little night dress for me to wear. We snuggled with each other in the same warm bed. I fell asleep with the feeling of a freshly fucked ass and three pairs of tits pressed against me, one pair of which was mine.

I smile happily because I knew that with a bit of luck I would get to do it all again tomorrow, except this time it wouldn't be a plastic dildo. It would be with a real cock with a real man attached to it.

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • A Night Out To Remember Ch. 02

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 514 milliseconds