@cant_into @lizzeboof @nosleep @karen @pea @DetectiveHyde

(Pardon this is going to be a slow burn getting to the action; exposition to set up the scenario and all. The first person story telling is not intended to mean this actually happened, just the voice I want to use.)

After being away from Austin for 8 years, due to work, I finally returned. Now 38, married and with 2 boys, and a mostly sexless bedroom as my wife's libido was low and she pretty much only liked missionary. We settled into our new home and invited our old friends over for housewarming. Of course, there would be some new faces in that circle and we wanted to meet them, too. That is when I was introduced to Jean. Our mutual friends must have let her know that we were very trans-friendly, in spite of being a straight cis couple, because she wasted no time identifying herself as trans. She passed very well, dark hair that sometimes covered an eye, glasses, and a slender body; a-fucking-dorable. At 21 years, she was the 'little sister' of the group. If I had even met her when she identified male, she would have been 15 anyway, just a 'kid' at the anime club.

A couple more social gatherings go by and soon we had Jean as a regular guest in our home, watching anime, playing video games, and smoking weed with us. She said that she felt safe with us, like the parents that she wish she had. I began to spoil her like the daughter I never had... but then, something happened that I never expected...

This night, my wife and the boys were visiting her mother in Houston. I had the house to myself for the whole weekend, considering what kind of porn I wanted to view for a spank session; big girl, small girl, interracial, DP? The possibilities were endl...

DING DONG

I looked at the monitor panel and saw Jean, in that skirt and thigh-highs fashion that was my main fetish, crying on my doorstep. In gym shorts and an old t-shirt, I opened the door.

âWhat's wrong?â I asked.
Jean sobbed, âMy asshole bigot parents drained my bank account and shut off my credit a couple months ago. I tried to do it on my own, but I couldn't make rent 'cos my checks go to that account!â
âCome inside, we'll set you up here for a while.â
*sniffle* âThank you.â

I made a frozen pizza and we had a couple beers while Jean talked about how her parents kicked her out at 18 and she'd flopped with friends until she could get a job to get her own apartment. She had been doing fine until her parents called her bank, because the account was still under her dead-name, they claimed 'he' had died and someone was stealing 'his' identity. I hugged her and pat her head, not able to respond or fathom the despicable actions of the people who were supposed to be her first 'safe-space', while she cried on my chest.

After she settled down, we then went to the den to watch some anime. On the couch, Jean snuggled up to me, breathing heavily while I pat her head. I tried to ignore my slowly thickening cock, but almost unconsciously, I started to caress her thigh. I hadn't even sat with my wife like this in years. My mind was getting foggy with the first twinges of horniness. I was about to cheat on my wife and have my first non-heterosexual experience and I couldn't care less at that moment. There was no going back as long as Jean was receptive. I lifted her chin and kissed her lips, and again, and again. Jean's hand had slid up my shorts leg to begin stroking my bulging penis while she kissed behind my jaw and nibbled my ear. Simultaneously, my hand had moved up her inner thigh to tease her dick thru her silky panties. Jean pulled back a leg of my shorts and boxers to reveal my cock. Impressed by the size she purred, âMmm, daddy!â (Daddy? Fuck it, roll with it.) and dropped her head down to lick the precum gathering on the tip. In turn, I lift her skirt and pull her panties aside to expose her dick, not as large as my own, but uncircumcised and still of an average length and girth. I slid back her foreskin and rubbed her precum around to lubricate her head; Jean shivered and moaned as she took my cock into her mouth. âOh, god, kitten!â I exclaimed, âI haven't been blown in years!â My wife hadn't sucked my dick since we were dating. Out of curiosity, I gathered some of Jean's precum on my fingers and gave it a taste. Salty, not entirely unlike pussy, but different. I was intoxicated with lust for Jean. âOh, fuck, no woman has ever blown me this good!â Jean moaned in girlish pleasure for the praise. With one hand I was stroking her cock, with the other I pat her head. Leaving my cock sloppy with her drool, Jean come up to say, âAm I a good girl, daddy?â I replied, âYou are a naughty kitten!â and brought her face up for a deep kiss.

Jean then straddled me, slowly easing my cock raw into her asshole. Her cock twitched as she slid all the way down. âDaddy, your cock feels so good in my ass.â âFuck you are so tight, I might just cum.â She's grinded on my cock as I took off her blouse, revealing her flat chest. âDon't stop patting my head, daddy.â I complied to her request, meanwhile I stroked her cock and began licking her tiny nipples to pebbles on her chest. âAh, ah, right, there, you, are, hitting, my, spot.â she called with each thrust of her hips. âNNNNNNNN!â she called as her cock jerked in my hand and began to ejaculate. I started to ask, âDo you nee...â but before I could finish the question she animalistically said, âDon't stop fucking meeeee!â

I stood up, carrying Jean with my turgid cock still in her ass, hers still rigid as well. I walked with her stockinged legs wrapped around me thru the house to the bed where I had boring vanilla sex with my wife just the night before. The bed was a perfect height that I could stand beside it and fuck my partner, which is what I did with Jean. I lowered her onto the bed, pulled her feet up to my shoulders. As I relished the feel of her stockings on my hand, I began to thrust harder and faster with each stroke into her ass. âYes, daddy, fuck me! Fuck me! Fuck me, daddy!â I was getting close, now fully on top of her with her legs wrapped around my waist, so that I couldn't pull out even if I wanted to. âCum inside my sissy ass-pussy!â Jean lewdly cried out. No more sense, just lust as I ran both of my arms under her shoulders to stroke her head and deeply kiss her mouth, stiffling her loud moans. My orgasm was building as I thrust full shaft into her asshole. Jean stiffened, arching her back and she ejaculated again. I could feel her hot semen between us as I began to cum in tandem. I withdrew my cock from Jean's gaping asshole; my load dripping out of her onto the bed were my sons were conceived. I'd just had the best sex of my life, with a trans-girl. Instead of guilt, I felt relived. I realized at that moment that my attraction was more than for âwomenâ. Our night together was not over... (Next one will be shorter)