Party Surprise - First sex as a Crossdresser.

This is a work of Fantasy. I hope you enjoy.

Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly she was jealous of my legs. She was a petite sexy woman and we were almost the same size but I still had my own stuff that I’d secretly obtained from eBay and op shops.

I didn’t consider myself bisexual, certainly bi curious at least. I liked watching guys stroke on cam and enjoyed the odd bit of cybersex online when I she was at work. I also loved tranny porn or porn where cross dressers were involved. I loved the idea of a cock in panties.

We discussed my “desires” now and then and I did admit that maybe I’d like to feel like a woman one day. We also discussed 3somes but the idea of her having sex with someone else upset me and me having sex even with a guy was like cheating so it was a line I didn’t think I would ever cross.

But I did secretly desire sucking a cock and being anally penetrated. I used dildos and plugs and we even introduced them in the bedroom and Stephanie did enjoy fucking me with her favourite dong.

A friend of ours was having a New Year’s Eve party and as luck would have it was a costume party. I secretly wanted, well hoped, I could get all dolled up and go as a girl. We discussed what we would wear over several weeks and finally Stephanie suggested I go as a woman and she would dress in a tux and go as a man. I feigned resistance but was secretly beside myself.

Over the next few days I contemplated several outfits and with Stephanies permission I decided upon one of her favourite dresses. It was a black slinky, stretch jersey that had a cowl neck and was figure hugging. It wasn’t my favourite satin but it felt diving to wear. Teamed with seamed stay up stockings and black 6 inch heels it looked demure and sexy yet elegant. Stephanie and I went shopping for lingerie and she selected the most divine red and black satin G string panties and a red and black matching bra, together with a red satin under bust corset to improve my figure. I stopped short of trying them on in the store but god I wanted to.

The night came and I showered and shaved and punt on my panties and bra filled out with some silicon falseys. Stephanie helped tight lace me into the corset which felt divine. She then sat me down and applied my makeup. She had never done this and the experience was just so erotic I was rock hard sitting there. When she finished she combed out one of my wigs, a shoulder length brown wig that I always thought looked good on me. She then revealed me to the mirror and I gasped. I had never seen myself look so good. God I was sexy and even I thought I was passable. Dark smoky eyes and deep brown glossy lips than were lined immaculately.

Now for the dress and slipping it over the lingerie felt even better than I remembered when I wore it weeks prior without her knowing. Slipping on my stockings and heels, and elbow length black satin gloves, standing before the mirror was an elegant and sexy woman. Yes that’s how I felt and a woman.

Stephanie even said to me, “I have to tell you, I’d fuck you”. That comment really made my insides jump. I felt and looked great.

I went downstairs and waited while Stephanie got ready. After 30 or so minutes she appeared, hair slicked back wearing a black satin tux complete with bow tie. She hadn’t gone for the man look but had applied dark, almost slutty makeup. God she looked hot. She also was wearing 6 inch black stilettos which just set the whole outfit off. She looked hot.

I don’t normally smoke except when dressed and so we popped outside in the cool and both had a cigarette and a glass of wine. It felt great standing there dressed to the 9s with my wife dressed as we were.

So we headed to the party which was not far from home. She drove as she was the “man” for the night. It did feel nice as she opened the door for me and I slid onto the leather seat and she closed the door.

Arriving at the party we were greeted by one of our hosts, Michelle who was dressed as a playboy bunny. She didn’t quite have the figure for it but she looked sexy none the less. She picked who Stephanie was but had to ask who I was and was visibly surprised when she was told it was me. I think I went a bit red as she patted my bum and said “ooh, don’t YOU make a sexy dish?”

Stephanie explained that my name was Trish.

We went into the party and there were about 30 or so people drinking cocktails wearing various costumes. There was a Mr Spock and a few French maids, a couple of women in suits and there also some people who hadn’t made an effort. A couple of casually dressed guys and women. Bit disappointing I thought; they could have made an effort.

After an hour or so Stephanie and I separated and she caught up with friends and I was talking to a couple of women who continued to complement me on my looks.
At one point a glass of champagne was thrust into my hand by a guy who introduced himself as Paul. He was a well-built guy in his early 30s, and I guess he was good looking. He was a bit taller than me in my heels. He was one of the non-costumed guys at the party. He said he worked with Stephanie and thought I looked fabulous.

He asked my name and we made small talk for a little while and then there was quite a bit of innuendo and I realised we were flirting. I was incredibly turned on by this especially when it became obvious he was coming onto me. He would gently rub my bum or put his arm around me. I loved the attention and the several glasses of champagne he plied me with made me lose my inhabitations.

After an hour or so of standing my feet were getting a little sore and I was dying for a cigarette. Paul explained that he actually lived at the house where the party was in a bungalow out the back. He said I could have a sit and a smoke out there if I wanted to. I thought why not and we slipped out into his room.
For a bungalow it was roomy with a single bed, a TV and fridge and a leather couch. The place was tasteful and the bedside lamp which was on gave enough light without making it bright.

We sat on the couch together, not too close and taking the wait of my feet was great although I left my shoes on. I lit a cigarette and relaxed back onto the couch. With that Paul picked up the TV remote and turned on the TV. Straight away there was a porn scene showing. A big black cock was humping a gorgeous white ass which as I watched saw it belonged to a hot tranny. She was absolutely loving the anal fucking she was getting.

My cock sprung to attention straight away.

Paul asked if I liked tranny porn. “Are you k**ding?” I said. “I adore it”.
So I sat and smoked and drank more champagne watching this lucky bitch get reamed by this enormous stud.

I was transfixed by the video and the champagne had dulled my senses a little. I didn’t realise that not only had Paul moved closer to me on the couch, but he had also taken out his very erect cock and was sitting next to me stroking it. When I looked to my right and saw his cock my eyes nearly popped out. It was gorgeous. At least 8 inches, dead straight, cut and not too thick. God it look good glistening in the soft light and the reflected TV.

“You’re obviously enjoying the video” I said jokingly, my eyes never leaving his cock. Paul replied, “Well, it’s not so much the video, more sitting next to you, you are so sexy”. I must admit I melted a bit when he said that.

I asked, “What, I make your cock hard?” “Yes, very”, he said.

“Would you like to touch it?’ He asked. My god did I, I thought. “Um, no, I better not, it’s not right, I mean…”. “Don’t worry” he interrupted, “It will be our little secret. No one will ever know”.

It was a mix of the champagne, the moment and the fact that was so god dam horny, but I wanted to touch this glorious cock so I reached out my gloved hand and gently touched it. This was the first erect cock I had seen (other than mine) in the “flesh” so to speak, so to be actually touching it was just out of this world. Paul took his hands away and my hand edged close. With gloved finger tips I gently touched it like you would when checking if paint was wet. Once the initial barrier was broken I gently grasp it mid-way and instinctively began to move my hand up and down.

Paul let out a low moan and said softly, “MMM that’s it baby”.

I firmly held it now and was started to move in longer strokes. I was jacking a hard cock and it felt great.

It felt warm and oh so hard and without even thinking and leant across and kissed the tip. I then licked it like and ice cream. It tasted salty and oh so good. I then opened my lips and the head of Pauls cock was in my mouth. It felt divine and I gently lowered my mouth down his hard shaft and he spoke more encouragement, “Oh I so hoped you would do that sweety. Oh yes, that’s sooo good”.

I really started to get into my role as a cocksucker. Bobbing my head up and down, removing my mouth and gently licking, kissing and biting his shaft, but I wanted greater access to his balls so I topped and told him to remove his pants. He stood up and almost ripped his trousers off and stood before me.
I looked up into his eyes as I took his hard cock into my ready mouth again and as I did I tickled under his balls and reached around to tease his arse just liked I liked. His cock grew even harder if that was possible and he moaned deeply. It wasn’t long before he placed his hands on my head and started to thrust into my mouth which I absolutely loved. I could feel him start to twitch and thought I was about to taste my first cum but he stopped and pulled his cock away. I looked up at him quizzingly and he said, “I would really love to fuck you”.
I was shocked. Was this a line I wanted to cross?. Without hesitation I said, “I never thought you’d ask.” I had never wanted anything so much. I wanted this man inside me, deep inside me to feel like the woman I know I looked like and wanted to feel like.

I turned around and placed my knees on the couch and my hands on the back. As he gently lifted my silky dress I asked, “No one will ever know about this will they?” Although at this point I was beyond caring. Paul assured me, “No babe. This is our little moment, our secret.”

Then he said, “Oh shit, I don’t have any condoms”. At this point I didn’t care. I wanted him inside me and overtaken by lust I wanted to feel his seed in me. “I don’t care, Paul, I just want to be fucked.

He pulled aside my silky G and gently touched my hole. I bit my lip in anticipation. One, then 2 fingers entered me. “My god, you are slippery already” exclaimed Paul. I replied, “That’s cause you get me wet” and giggled.
I felt his hard cock slip up and down between the cheeks of my ass then a little pressure and he was inside me, just a little. He stopped and let me relax and when I pushed back on him it was his cue to make love to me. He slowly and gently eased his gorgeous cock deep into my bowel. It felt even bigger than in my mouth. I felt his balls touch mine and felt him deep inside my belly. “Oh god that’s good” I murmured. He then withdrew and plunged into me again and I gasped, “Oh god yes. Fuck me Paul”.

He then started to move in and out of me more quickly. I can’t explain how I felt. I was being fucked. I felt so complete with this man’s organ deep inside me, mating with me. I truly felt like a complete woman at that point. Especially when he was moaning, “God your tight” and “Oh you are such a good fuck”. I loved it.
His thrusts became more urgent and I found myself pushing back with his movement forward, fucking him back. He stammered and said “Where do you want me to cum?” I said straight back to him, “Cum in my ass Paul. I want your seed in me. Breed me like your bitch”. I know this was wrong but you sometimes do silly things when you are overcome by lust.

This was enough for Paul. I felt him tense and his cock grew inside me and I felt it twitch as his first hot cum filled me. I actually felt it deep inside me. This was enough for me. My cock was still hard in my panties and I hadn’t even touched it but my own orgasm was shared with my lovers.

Panting and overcome with emotion, Paul pulled his cock from me and I turned and took his softening cock in my mouth and clean my and my juices from him. I then stood and if being fucked wasn’t enough I put my arms around him and kissed him passionately and deeply. Like two lovers who had just climaxed together, which indeed we had. I whispered in his ear, “can we please do that again sometime? I love fucking you”. He grinned and said, “god yes babe. Best fuck I’ve had for a while”.
We sat back down on the couch and I
had a cigarette before re applying my lipstick at the mirror next to Paul’s bed. I adjusted my dress and he put his pants back on. I looked at him and jokingly said, “Thanks for the fuck”. We laughed and I re confirmed, “Our secret?” “Yes, for sure” he said.

We went back into the party and I quickly found Stephanie. She was alone outside on the balcony having a cigarette. I lit up as I joined her. I was waiting for the “where have you been?” and was trying to think of excuses when Stephanie turned to me and gently stroked my hair. She said, “Did you enjoy that my darling?” I was confused and said, “Wha, what are you talking about?” With that Paul joined us on the balcony, walked up to Stephanie and they shared and deep lounge kiss. My eyes were wide again. What was going on?

Stephanie, with one arm still around Paul, turned and looked at me but directed her question to Paul. “Was she good sweety?” I was agasp. “She was everything you promised babe”. They kissed again. I then saw Stephanie pull a $50 note from her pocket and hold it up as though she had lost a bet or was making payment. Still looking at me she asked Paul, “Did she let you bareback her?” “Sure did” he smugly replied. Another $50 was offered. Then she asked, “And did you cum inside her?” “My god, did I?” He replied. Yet another $50.

Stephanie then cupped her hand onto Paul crotch holding the cock that had just fucked me. She said, “Babe, this cock has been fucking me for several months now. It just seemed so wrong not to share such a gorgeous piece of meat with you. But you have disappointed me. Letting a man cum in your ass on the first date, I’ll have to teach you some etiquette.” They both laughed. I still couldn’t speak. I’d been set up. When I finally spoke, I asked about the money. “Well Paul bet me $50 he could fuck you, $50 that he could bareback you, and another $50 that he could get you to let him cum in your ass. So you cost me $150. But it was worth it knowing what he just did to you” and she laughed again.

I honestly thought this would be the end of us and she would embarrass me or punish me. But over the next hour we stood on the balcony and smoked and drank and she explained how she knew of my bi tendencies and wanted me to experience sex as a woman and how she was so proud of me. She went on to tell me some of the other things she had planned and as I truly hoped, that ongoing sex with Paul with both of us would continue. She even asked if I was interested in a 3some with her and him. I smiled and said,” only if I get his cum”

“MMM she said. I’ll toss ya for it”.

99% (95/1)
Posted by SatincdAus
2 years ago    Views: 2,895
Comments (26)
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2 months ago
very hot babe
6 months ago
i like swing with you and wife
6 months ago
7 months ago
Well done!
1 year ago
Not only a very sexy story, but brilliantly written as well. Bravo.
1 year ago
Interesting fantasy!
1 year ago
Hot story, hard to put down... ;)
1 year ago
WOW, awesome story... So HOT!!!
1 year ago
excellent story!!!
1 year ago
what a hot story
1 year ago
fantastic got me dripping with precum
1 year ago
wonderful story
1 year ago
A great story!
2 years ago
nice story!
2 years ago
True story about you and the wife???
2 years ago
2 years ago
Great story
2 years ago
Damn great story! I need some cock now.
2 years ago
great story darling, i wish i could share paul with you!
2 years ago
fantastic story made me cum really hard and wet thanks
2 years ago
Great story,would love to have an experience like that
2 years ago
I would love to meet a sexy couple like they only exist in stories..??
2 years ago
Very sexy story telling! Love the seduction and the promised enjoyment in the future still as equals. At least for Stephanie and Trish. Keep having erotic fun with the story telling! Hugs, Jenna
2 years ago
now that was so hot came in my panties you are a great writter would like to see where this goes
2 years ago
fucking good loved in
2 years ago
Good story.