Tranny Night Out and One Kinky Session

Guess I should start by explaining myself, as a young guy I always knew I was not the same as a lot of my friends and enemies for that matter, girls had no interest in me at all apart from ones who were long term friends.

I knew something was wrong but never worked out what it was till one evening whilst dating a girl named Becky I had met on an online dating service who seemed to accept me for who I am.

We had been dating for 3 months or so and I always loved the feel of her stocking clad legs and seeing her in sexy lingerie, but I secretly was always thinking about how good the items would feel against my slim torso.

I was not sure if she knew that I secretly craved to become a girl in secret and she definitely did not know about the times I had worn stockings while playing with myself and stroking my thighs encased in silk.

One evening as we sat cuddled up together going through our local paper she saw an advert for The Rocky Horror Picture Show coming to our local theatre. With that she asked if we could go and I felt suddenly in a state of shock especially as I knew all about the cross dressing bit of going to the show.

Eventually I agreed we should go and she suggested that I go in drag as a convincing girl, of course I wanted to but I did not want her to know about my secret. My long time desire to dress like a convincing girl and be used like a girl too.

The following morning we got up early and called the theatre to book our tickets for the show, have some breakfast and get dressed before going down to the town centre. On our way down we passed several lingerie shops and Becky or Beck's as I frequently called her suggested we go into one of them and look around.

Again I felt the flash of fear rush through me as I was always uncomfortable in those stores even when buying lingerie for others let alone for myself, but I submitted to her and followed her into the store cautiously looking at the store clerks to see if I knew anyone.

As we walked around Beck's picked up a couple of Basques for herself holding them against her slim body and asking me if I liked them, of course I did. I loved my girl in lingerie but always wanted to be in her place.

We continued around the store for a while with Beck's picking up several items she liked, by now I was relaxing a little and looking forward to not only heading down to the pub for a sly pint shortly but seeing the gorgeous Becky in her lingerie when we got home.

Then she caught me totally off guard with a question asking me "Anything you like for our night out?"

I stammered slightly with night out, huh what and she reminded me I was to go in drag to the show the following weekend.

I was in a place full of lingerie and I was scared to death of what may come of me not only looking at but buying lingerie for myself but Becky carried on with you will need something to wear as mine wont fit you.

With that comment the attendant looked up at us both, she was a slim blonde and probably a local student. Now I was really nervous as she stood there behind the till. I knew she was the only one who would know for now apart from my girlfriend and she was encouraging me to cross dress.

I knew what I wanted though as I had already spied a gorgeous sating black and purple Basque I really liked so I told Becky and she agreed it was sexy. After picking my Basque she helped me to pick my panties and found a gorgeous pair in black lace with little bits of lace in the same purple as the Basque. Little did she know I was actually semi hard in my briefs thinking about dressing like the girl I had always wanted to be.

With that we paid up at the till with Beck's making a comment to the young blonde that we were going to the Rocky Horror Show and she was going to turn me into a girl for it. The blonde behind the counter just laughed lightly and took our money before we decided to leave.

By now I was ready for my Sunday lunch time pint and a paper to check the football results but Becky had other ideas. She carried the bags from the lingerie shop but insisted as we walked down the hill that we should stop off at a shoe store, it was nothing special. A cheap kind of everything on display shop so no attendants to worry about till you had to pay and they were not bothered by what was going on in the shop as they were to busy discussing their night out and who they had shagged.

Becky dragged me down through the store to where the woman's high heels were located and she instantly picked up a very sexy pair with ankle strap and a good 5 inch heel in patent black, I even told her how sexy she would look in them. Then as I had guessed she told me to select a pair in my size.

I was starting to get used to this now and it was obvious she wanted to turn me into her girl for the night, with that I picked up a gorgeous pair of black peep toe heels with a modest 4 inch heel. She agreed to them and told me they would look good with my Basque as they had a colored sole as well in purple.

I had to have a minute to myself so as Becky went to pay I left the store and sat on a wall just outside the door waiting on her to join me.

A couple of minutes past and she appeared from the store and came over to give me a kiss, as I did I felt the throbbing of my cock again and she sensed I was turned on already at the thought of dressing and being with her fully dressed.

By now I was not only becoming more broke by the minute but I really wanted my lunch time pint to settle the nerves so we walked on and into our favorite pub. We sat at a table near the bar so I could watch the football results from the early games coming in. As I sat nursing my beer a waitress by the name of Emma we both knew came over to say hi and Becky just could not resist telling her we were going to do the Rocky Horror evening. To my surprise she told us that she and her boyfriend were going to and she was also going to dress him up.

For me this started to sound interesting and Becky seemed to know that I would be more chilled if we went as a four some of sorts, and to be honest me and Emma had a bit of history as we had some casual sex before she got with her current guy Marc.

Marc knew of our history but Becky had no idea I used to drink there and wait for Emma to finish so we could go have sex either at mine or in one of the two swingers clubs in the town hidden away. She also knew I was bi and had seen me engaging in oral sex with other guys in the clubs.

With a sly wink in my direction she went rushing off to deliver the next hungry punter their dinner and then the question came from Becky.

Why did Emma wink at you as she left?

I knew I had to tell her so I told her straight that I and Emma used to have a casual arrangement before me and Becky had met or got together at least. To my surprise Becky was totally cool about it all although she had no reason to not be. Of course I had neglected to tell her about the guys I had sucked off in the swingers club near my flat in town.

After an hour or so we went to leave the bar and Emma came bouncing our way asking if we could arrange a good time to meet up on Saturday for the show. As Becky now knew mine and Emma's history she suggested that Emma bring along Marc and the girls dress us boys at my flat as it was only a 5 minute walk to the theatre in town.

With that we all agreed that around 6pm on Saturday would be best and then we could have a few drinks to relax before dressing and going out.

I knew Becky would be feeling a little odd meeting a girl she already knew but not knowing I used to have regular sex with so I put my arms round her pulled her close and kissed her telling her she was gorgeous. With that we were back to normal and I gave Emma a peck on the cheek and left.

As we were walking back to the flat I knew there was a wig shop round the corner from my place as a lot of the towns transvestites used to use it to get there hair pieces. My flat was after all on the edge of the town's gay area so you always saw an interesting mix of people around. I always loved living there and it was easy if I ever got up the courage before meeting Becky I could walk just down the road and go to a gay bar on the pull for convincing trannies.

Becky agreed she should tag along to the wig shop and as it was mid afternoon on a Sunday they had closed but left a mobile number on the door. I was unsure but Becky told me to call it as we needed to get sorted and did not have time in the week due to work.

I hesitantly called the number and what sounded like a gay guy answered and told me to wait 2 minutes and he would come down to help us. I was kind of surprised that a gay guy should be running a shop basically for trannies. The shock did not last long though as a leggy transvestite came to the front door and unlocked welcoming us in and locking the door behind us.

In fact the Trans girl who ran the shop was actually very convincing and I found myself checking out her bum as she showed us round the styles she felt would suit me. In the end I picked a raven black shoulder length wig that fell over the edge of one eye. It made me feel so girl like and once again the bulge in my briefs came back. This time I was not the only one aware of it with the trans girl who ran the shop clocking my package and telling Beck's she was a very lucky girl to have such a nicely hung man or girl to fuck her.

We found that the Trans girl running the shop called herself Vanessa and Becky found her not only amusing but admitted to me later that she would love to have sex with her. This turned me on even more as if she liked Vanessa did that mean she would like me as a girl?

As Saturday evening came round the buzzer for the front door went just after 6pm, knowing it would be Emma & Marc I bounded downstairs with a bottle of lager in hand to meet them.

Emma looked sexy as ever and I invited them in shaking Marcs hand along the way. I guided them up the stairs and down the corridor to our comfy lounge full of big soft leather sofas. Emma and Marc sat across from me and Beck's for a bit enjoying a drink and each others company.

After a hour or so the girls went off to our bedroom to get ready and I slowly started conversation with Marc, as it was the first time we had met the conversation revolved around football, beer and the girls. He then built up the bottle to ask about me and Emma and I told him that it was a friendship and casual sex pact we had made but it had since ended due to both of us meeting partners since.

He also mentioned that Emma had told him I was bisexual and I waved my hand at him to keep it down as Becky did not know. He replied with that's cool I am too. Now the party was really looking up as Becky had expressed an interest in Vanessa from the shop before so I had to wonder if she had ever enjoyed another woman sexually as I knew Emma was bisexual and very kinky too.

What seemed like hours passed as Marc and I sat chatting about all sorts and then the girls came walking in. Becky in a black lace Basque and panties with stocking and her new 5 inch heels, her dark brown hair falling to her shoulders with the tips of her hair brushing the tops of her pert 38B cup breasts. Emma looked just as stunning in a PVC corset and panties set with black hold up stockings and 5 inch stilettos on.

I could not keep my hands of Becky and patted my lap for her to come and sit on, she took the hint and Emma did the same for Marc. Trying to be discreet I ran my fingers across her clit finding her to be moist already. With that she bent to kiss me and whispered into my ear that Emma had licked her out. My thoughts previously had been right she was bi and we were going to have a lot of fun later on.

What I did not know is that Emma had told Becky I was bisexual and so was Marc but again she whispered to me that she now knew and could not wait to see what may happen later.

With that me and Marc went to the bedroom to put on our lingerie and as Marc lowered his briefs I could not help but look at his cock and him at mine. Before I knew what we were doing we were stood slowly wanking each other off. He had a lovely thick 7 inches that I knew I could deep throat if he wanted me to. I complemented him on the size of his member and he jokingly said it's not as big as yours though and he was right as I had 8 1/2 inches of thick cock rock hard and ready for him if he wanted it.

We left each other alone after that and started to dress but soon found the sensation of slipping into the Basques and stockings too much. I noticed his cock straining at his panties so dropped to my knees in my wig, heels and lingerie and started to slowly suck him deep into my mouth. He stood there fully dressed moaning with pleasure as I flicked my experienced tongue round his bell end. He soon pulled away from me explaining he wanted to save his cum for later and helped me to my feet before he released my 8 1/2 inches and began to suck on me. He was obviously experienced as he really knew how to suck cock and I felt rushes of pleasure passing through my body.

I thought for a while I was going to explode into his mouth but held back as he had explaining I wanted to save it for later on. As he stood and we both relaxed and put our cocks back into the restrictive panties I asked if he had ever had full sex with another guy, he replied he had but only liked to give and not take cock in his anus but did add he may if he was relaxed enough.

As we were now both fully dressed we ventured into the lounge again to meet the girls and as we did I saw Emma on her back on the black leather with my Becky licking her pussy deeply. They both seemed to be enjoying each others juices already. With a start Emma told her to stop as she saw me and Mark stood watching both with rock hard cocks waiting for them.

Becky jumped to her feet and trotted across to me and kissed me full on the lips, her mouth tasted of a taste I knew well Emma's pussy. With that she took my hand and said lets go do your makeup. Emma and Marc did similar but after a couple of minutes we heard a loud groan from the lounge. I was told to stay where I was and Becky went to investigate, it turned out Emma had been sucking Marc off and he had cum hard into Emma's willing mouth.

Soon I was fully made up and looking convincing thanks to Becky who confessed she wanted to get fucked by me looking like a girl. I had no plans to fuck her before going out but she told me she needed my cock in her.

With that I stood slid down the panties and sat back on the stool, Becky wasted no time in mounting my rock hard cock and riding me while sliding her pussy soaked tongue into my mouth. I just could not take anymore with the feeling of her dripping wet pussy wrapped round my shaft and the taste of Emma's pussy in my mouth and I convulsed hard and shot my spunky load deep into Becky's willing shaved pussy.

She sat for a moment taking it the fact I had just shot my hot load into her and get over the orgasm she had as I did so. She kissed me lightly and rushed off to the bathroom to take her pills as neither of us wanted her to get pregnant yet anyway.

The time had soon come for us to go out to the show, it was dark and cold on the October evening and as we turned the corner we ran into Vanessa from the wig shop who complemented me and Marc on our look. We asked where she was heading and it turned out she was going to the show with her boyfriend, a hunky muscle bound gay boy called Phil. He was stunning but scary to look at but oh so sweet and soft if truth be known. He was also a tease as he grabbed my bum as we walked down and got told off by Vanessa for not looking after her.

I was so aroused not just because Phil had grabbed my bum but being dressed and out on the town with girls, a guy and two other trannies.

As soon as we got to the show we took our seats and waited for the curtain to open and lights to dim, as they did I felt a hand in my groin stroking my cock through my panties only to discover it was my gorgeous Beck's, I reciprocated the gesture by slipping a finger round the hem of her panties and stroking her clit. I felt her starting to get wet for me again and she moved my hand away and whispered to me that I was in for a show when we got home.

As soon as the show finished I could not wait to get home and Emma & Marc joined us, not to be rude I invited Vanessa and Phil too but Vanessa said they were going elsewhere for some fun with some friends but agreed we could meet for a drink another time if we fancied.

We soon reached the front door and all headed fro the lounge, I and Becky had a couch and Mark & Emma had the other across the table from each other. We all knew we were going to fuck together it was just who would make the first move. I felt the tension building in the room and decided to trot off to the kitchen in my heels to find a cold bottle of Champagne I had purposely put into the chiller before we left.

Heading back to the lounge I heard light moans coming round the door I saw Marc licking out Emma in front of Becky. To add an element of surprise I popped the cork on the Champagne and tipped a little into Emma's pussy as Marc lapped it up.

The rest I poured into 4 glasses on the table but made sure I kept a little as I planned to give Becky the same treatment, she was already fingering her rapidly moistening pussy as I pulled her panties aside and slid my tongue into her waiting clit. She knew what to do as she took the bottle of Champagne and poured a little over her wet cunt as I lapped at her making her orgasm hard from the cold Champagne running down her clitty followed by her girly love juices and saliva.

Emma had crawled over to us and kissed Becky full on and dropped to her sopping wet pussy and began to lick her out again, soon they were in fits of passion as they 69'd each other lapping at each others pussys.

I suddenly knew what I had to do as it was obvious Marc was not going to initiate the fun between us so I crawled on hands and knees across to him and knelt in front of him licking my made up lips.

He knew what I wanted and released his cock from his lacey panties for me to suck on, I wasted no time in sucking his lovely thick cock deep into my throat, as I felt his cock start to throb I stopped and got up from my knelt position and told him to get down on his knees and suck me off. He knew what to do and expertly got me rock hard, lapping up the pre cum off my stiff cock.

Little did he know what I wanted and I pulled him to his feet, kissed him hard and asked if he would fuck me. He agreed he would love to fuck my tight arse and bent me over the couch and expertly flicked his tongue across my puckered asshole. I was rock hard as I felt his tongue driving into my tight arse.

Soon I felt his helmet pushing against my love hole and a cold sensation which turned out to be cold lube dribbled across my anus. Soon I was in pain as his fat helmet eased its way into my anus, slowly sliding into me inch by inch till I felt his balls against my arse.

From across the room I heard Becky say go on fuck his arse, I want to see you fuck my gorgeous tranny girlfriend and with that he proceeded to start banging the arse off me sliding his thick 7 inches in and out of my arse. I loved it, I felt like a total slut getting banged in front of two girls I had fucked before. One of which her boyfriend was now slamming his cock deep into my arse.

After what seemed like all night long he pulled out of me and I felt a bit of relief as he did, I knew he only liked to top others so was suddenly surprised when he asked if I would fuck him now.

I secretly had fucked trannies before and knew exactly what I was doing, I warmed the lube between my fingers while I rimmed him hard, sinking my long tongue deep into his arse. I knew I had him nice and relaxed so I slowly lubed my 8 1/2 inches and his anus pushing the lube deep into his arse.