Crossing the Date Line

I'd been chatting with a man online for weeks, flirting with him and telling him what I'd like him to do to me.

I'd finally plucked up the courage to go on a date with him and had even been shopping with my wife to find a new dress for the occasion.

I was born as a man but now identify as non-binary I've been cross dressing for years gradually getting braver and wearing more and more.

My wife has been incredibly supportive of me through out this and even likes to have sex me in my female persona.

I'm 5'10 and very slimly built with delicate features so with a wig and makeup I can pass as a woman quite easily.

For my date tonight I took a very long bath and dehaired and moisturised all over, once out of the bath I put on my favourite black bra and thong that I had picked out earlier and then with help from my wife Carly I started work on my face applying makeup until I'd transformed into a beautiful woman.

I put on my long flowing black dress that hid my lack of beats but accentuated my ass and then for the last act of my transformation I put on my shoulder length red haired wig and I had become Rachel.

I was getting super nervous now but my wonderful wife gave me a glass of wine while I waited for my taxi into town and I calmed down a bit.

I met Daryl at a bar in town he was lovely immediately and led me by the hand to the bar, we had a couple more drinks and continued our flirting from online.

When it was time to go and eat he wrapped his arm around my body and cupped my ass and it felt wonderful.

The rest of the meal was a bit of a blur but towards the end I started to feel a bit naughty and removed my stockinged foot from my heels and began to stroke his leg. His smile told me how much he liked that so I leaned back a little so I could raise my leg higher and stroke his thigh.

At this point I asked him in a quiet voice if he would like to come back to my house, he nodded so we got the bill and left hurriedly.

In the cab we made out for the first time kissing tentatively but gradually getting more and more passionate.

I broke away to message Carly I wanted her to be part of this and he knows I'm married but not yet something intoxicating was coming over me and I wanted him to myself so I asked her to wait upstairs.

We tipped the cabbie and unlocked my front door.

Then I whispered in his ear "stand still"!

I kneeled down so my face was inches away from his cock and then I started to fumble with his belt unlocking it then unbuttoning his slacks.

I reached into his pants and released his cock which pointed straight at my forehead I could see the tip glistening with precum.

I grabbed it with both hands one hand around his balls and the other around the shaft, I began to pump it and I heard him groan and with this I leaned in and kissed the top.

I'd never sucked a cock before so I took my time gradually opening my mouth further and taking more and more of him inside me.

After I while I stopped looked up at him and said please fuck me.

He nodded back so i stood grabbed his cock in my hands and led him upstairs.

Carly was waiting in the bedroom like I'd hoped I introduced them and then said I please both of you take me.

They stood around me and slowly removed my dress playing with my body as they did. As my dress feel away you could see my hard cock poking out of the thong that wasn't sufficient to restrain it.

Carly then led me to the bed and told me to kneel on the edge of it so my ass was nice and high and then leaned my forwards so my body was stretched out.

Carly then began to lick my ass hole to start getting me ready for Daryl while he waited he came round onto the bed naked now and laid his hard cock on my cheek.

He played it across my face drizzling me in precum and then finally let the tip slip into my open mouth.

I started to try and suck but he placed a hand on my head to stop me and instead he gradually began to move himself in out of my mouth gently face fucking me deeper and deeper until he was groaning and his hairy hips were almost touching my face.

I felt Carly stop licking me and guessed she was watching this hot scene but I was wrong she slipped a finger to my ass and started to probe pushing me as much as she could.

Suddenly Daryl stopped and pulled out and declared he was wet enough, he stepped round to the end of the bed and I heard the squelch of lube then a lump of the cold jelly landing in my ass.

I couldn't believe it was time I was finally going to get fucked by a real cock after years of thinking about it now was the time.

Carly lay down on the bed In front of me and I could smell her pussy which she started to position next to my face she told me I was allowed to start licking her until Daryl was in me as she wanted to watch my face as he entered.

With that I felt the tip of his cock rub the lube around my ass and then gripping me with a hand round each hip he slowly began to push against me.

It felt enormous bigger than anything I'd ever had but slowly I dilated to enough to take his head and then he was in! It felt amazing he just held it there letting me adjust for a while and then he pushed and pushed until his hips touched my butt.

I gasped I'd never felt so full, with that Carly grabbed my head and pushed it onto her soaking pussy.

With each of Darryl's slow strokes i was pushed into Carly's pussy licking her clit and trying to suck on it before I was pulled away.

He started to pick up his tempo fucking me harder and my face was ground further and further into my wife's pussy.

After a few moments Carly sat up and moved away to watch as Daryl fucked me harder and harder then she moved closer to him and leaned in to kiss him while his cock was still buried deep inside me.

He stopped and held himself in me while they passionately kissed each other, Carly started to moan and giggle and then suddenly I felt a hand grab my cock and start to tug at it, jerking me rhythmically faster and faster.

Then all of a sudden Daryl started pumping inside of me hanging slamming his large fat penis into me while Carly jerked me off in time.

I could feel my orgasm building and as I was getting closer and closer I found it harder to hold myself up my arms collapsed my face falling into the sheets as I moaned in ecstasy, this felt so much better than when Carly had pegged me before!

Then all of a sudden Daryl and me were cumming at the same time I fell onto the bed as my cock spurted all over Carly hand and Daryl pumped me full of cum.

To be continued.