“Tee” is very special to me. Our relationship started after my first deployment to Afghanistan and my first experience with a trans person. I suppose I had a whole new world opened up to me sexually, one where the sex wasn’t defined by gender roles, but rather the connection and passion alone. The “equipment” used was meaningless!
Aria was unavailable due to incompatible schedules and I had duty at the base again. The base was in the next town over from where my family and I resided, so I was confident that my extracurricular activities were safe from being discovered (I was right about this too, which allowed me many more experiences than I’ve been able to have since).
Once again I placed an ad, but this time specifically seeking a transsexual. I stated that I had my first experience and wanted more. Tee answered my ad, but stated up front that she was a full-time crossdresser. No hormone therapy and no intentions of physically changing genders. She had a prosperous beauty salon business and lived, dressed and existed as a woman.
We were working out the details of meeting, I would come to her house that was very near the base, when she asked me about my experience with receiving anal. I replied that I had nearly none, except that years ago I had used my wife’s toys on myself when masturbating. She then wanted me to know that she liked to “call the shots” and if we met, I WOULD get a lot more experience. I balked a bit, but she assured me that she knew what she was doing and that it would be worth it.
Once again I stepped out and took a chance… and yes, it was worth it!!!
I arrived at her place in uniform, I had my duty phone with me and we had established that if called, I would have to bail immediately and there would be no hard feelings (lucky for us, nobody on base did anything stupid and we had several hours together uninterrupted!). Her house was beautiful, clean and well maintained (I tend to notice the details, it has kept me safe many times). I rang the bell and stood back a bit from the door while she checked to make sure I was who she had talked to, a smart thing to do when finding a hook-up on craigslist!
Opening the door and letting me in, Tee greeted me wearing a green satin, ankle-length dress with spaghetti straps. Tee was Filipino with long, straight, all natural, black hair that reached half way down her back. She was almost a full head shorter than me, and just on the thicker side of skinny. As she let me into the living room I could see that she wore a black, lacey, strapless bra and matching thong. Her home was immaculate and decorated in a conservative mix of American and Asian artwork and furnishings. Sitting, I removed my shoes, and she prompted me to take off my socks as well, but she wanted the fun of removing the rest of my uniform herself!
Taking my hands and bringing me to my feet, she led me to a place she had obviously cleared before her couch. There were towels within reach and I spotted a tube of lube hiding behind a cushion. As if I wasn’t nervous enough, that sight alone got my heart racing! Standing facing each other, she felt my heartbeat with a hand on my chest, and in a quiet, soothing voice, reassured me that we’d enjoy the night and only do what we wanted to, nothing more.
She turned her face upwards and proceeded to kiss my face and lips, placing my hands on her smooth arms, I returned her attention with eagerness! She was a lovely kisser, with soft, gentle and yet hungry lips. Her tongue was skillful and insistent, sometimes teasing, and sometimes thrusting strongly deep into my mouth. We continued to kiss and neck while I used my hands to explore her body through the slick satin dress; caressing her back, groping her ass and grasping her hips to grind her growing bulge against mine. Her hands began to unbutton my uniform, setting my shirt neatly aside before pulling my t-shirt off over my head. She began to kiss, lick and nibble on my chest and nipples but I urged her to pause so I could take a step back and drink in the sight of her, committing it to memory.
Her hair was slightly mussed, her subtle lipstick now gone. One strap was hanging limp on her arm, the top of her bra exposed on that side. Her form was clear through the dress, I could tell where her belly button was and just below that, straining against the satin, was the clear shape of her cock, about two inches of it raising above the top of her panties and the best part; a tiny wet spot showing through the dress at the tip! I could tell her cock was very similar to mine; a little over seven inches, uniform thickness from base to tip with a well-defined mushroom head (her head was a bit fatter than mine though).
Thanking her, I drew her back and she immediately got my pants unbuttoned and carefully kneeling, she set my trousers aside with my shirt and began to use her mouth to tease my hard cock through my underwear. She pulled the waistband out a bit, allowing my cock to spring up straight and let the waistband back, holding my cock against my belly. She used her tongue to tease the head, getting it slick with her spit and my pre-cum. All at once, she pulled my underwear down and off, and before I knew it had slid the entire length deep into her mouth until the tip pressed against her throat. She slowly slid it back out of her mouth, placed a kiss on the tip and stood up. I couldn’t resist holding her face in my hands and kissing her deeply!
It was my turn now! As I kissed her, I slid the other strap off her shoulder and gently pulled her dress down to her hips. I kissed down her neck to her chest, spotting the “falsies” in her bra, I decided to leave it on her, but not before pulling one cup (and falsie) down to lick and bite a nipple for a minute. I proceeded down to her belly button and licked and sucked on it for a bit, telling her how much I loved it. Kneeling naked before her, I pulled the dress off her hips as she stepped out of it. She now stood before me, naked except her bra and a black lace thong doing a poor job of holding her cock in check!
Instead of removing her thong, I simply, gently, pulled it aside, freeing her completely hairless cock and balls. I moved my face forward, letting her cock slide along my cheek, so I could begin to kiss and lick the base of her shaft. I rubbed my face side-to-side across her hard cock, making sure the head slowly slid across my lips each time. I opened my mouth wide and sucked her balls into my mouth, sucking and licking each and both together, worshipping her soft, hairless balls!
Grasping her hips, I encouraged her to sit on the couch behind her. I guided her ass to the edge, and lifted the backs of her knees high and wide, granting me access to her perfect, hairless ass! She got the idea and held her own knees, freeing my hands to pull the thong aside and hold her ass up as I started to rim her gorgeous asshole for all I was worth! I alternated sucking and licking her balls and tongue fucking her asshole, I indulged my oral fixation for at least five minutes before she let her legs down, denying me further access to her delicious hole.
With her feet on the ground, I finally picked up her rock-hard cock and slipped it into my mouth. I began to un-expertly yet enthusiastically bob my mouth up and down her cock for a short bit before she gently stopped me and thanked me for the attention, but I could tell I was too rough and needed to learn how to do it right.
I kissed my way back up her belly, pausing to unhook and remove her bra this time. I licked and kissed her naked chest. She said she felt “undressed” without her boobs, but I assured her, her natural flat chest was much more desirable to me than the silicon falsies. With that, she grabbed my head and kissed me passionately with more force and desire than before! She pushed me back onto the soft carpet and pinned my hands to the floor with hers and continued to kiss me deeply while grinding her cock into my belly. She worked her mouth down my body, spending time on my nipples and belly button before stopping with her face between my legs. The next ten minutes were spent with her mouth, lips, tongue and hands sending waves of pleasure through my body as she focused her attention on my cock and balls.
She lifted my knees and had me hold them back and apart, she subtly grabbed a towel and placed it under me as she began to use her tongue on my back door. I apologized for being rather hairy, but she assured me that not only didn’t she mind, but that she actually enjoyed it. Her tongue went a long way to getting me relaxed, loose and lubed. She sat up kneeling and moved herself into position between my legs, I felt the hot, slippery head of her cock press against my asshole and I WANTED what was to come. She slowly pressed against my ass as I tried to relax. Bit by bit working more of her beautiful cock inside. I asked how much and she said she had about three inches in. I told her to fuck me, please.
She began to gently thrust against me, it was both painful and pleasurable at first, but began to get more painful. She said she couldn’t get more in, but had an idea if I wanted to try it. I said yes please, I want you to fuck me! She slipped out of my ass, straightened my legs and had me roll over on my belly.
I felt her reach for the lube as she straddled my legs and positioned her cock between my ass cheeks. She lubed herself up and spreading my cheeks, once again placed her cock head against my tender asshole. As I relaxed, I felt her head “pop” into my ass and continue to slide in… it seemed to go on forever! I felt inch after inch after inch slide into my hungry hole and IT. WAS. GLORIOUS!
She checked on me, asking how I was doing, I could only reply: “Oh God, fuck me! Fuck me! Fuck me!”
Starting slowly, she slid all the way in, and almost all the way out, her full length sliding through my asshole, sending shivers through my thighs and up my spine. Faster I whispered, and faster she went. Harder, I said, and harder she went! Deeper I growled, and her body began to slam into my ass, driving my cock into the floor. She settled into a rhythm, fast, hard and deep, I could only repeat, “oh god!” over and over! Tee began to make little feminine moans and grunts with every thrust, she wanted to cum, she asked me where, “where baby?”
I replied, “My ass, cum in my ass!” With that, she moaned loud and long and slammed into my ass harder and harder, grabbing my hips and grinding her cock as deep into my ass as she could. I could feel her cock twitching in my asshole, I wanted to feel her cum squirting inside me, but I could only feel her spasms with my asshole, inside I felt full of her cock, but nothing else… but it was enough, more than enough.
I think I fell in love with Tee a little bit at that moment. She lay on my back, breathing hard, her cock still twitching in my ass, getting softer and eventually slipping out. I just lay there, seeing stars and feeling her breath on my shoulder, her hot sweaty body against mine. I treasured the sensation of her cum beginning to run out of my asshole and down my balls onto the towel.
I was still in a daze when she whispered me to roll over. Her sweaty body slid down mine as I settled onto my back and as her mouth settled onto my cock. She sucked on my balls, tasting her cum and laughing softly before holding her hair back with one hand, my cock with the other and commenced to earnestly blow me.
She ensured I could watch her and within 30 seconds, I was groaning for release. She said “Give it to me! Let me have it all!” and as I stiffened and my vision dimmed, she thrust her mouth down onto my cock HARD! As I stared cumming, I felt my cock painfully hit the back of her throat, and then suddenly slip INTO her throat!!! I looked and her head was sideways to my hips, her face pressed hard against them, she pressed her throat onto my cock over and over in time as I came in gushes. The sensation was intense, the thought intoxicating, the spectacle, mind blowing! All too soon, I was done and she withdrew her head, I could unmistakably feel when my cock came back out of her throat! She gagged once mightily, and smiled at me unfazed with a dreamy look in her eyes.
That was out first time together, and definitely not our last. I had to get back to base. We were instantly comfortable with each other. We both walked through the house naked (well, she still had her cum stained thong on) as she walked me to the bathroom. She wanted to watch me shower and I gladly let her. She enjoyed watching me get dressed back into my uniform and as we kissed farewell at her door, I couldn’t resist dropping to my knees to kiss her on her dirty panties, smelling her cum and my ass as I mashed my face against her soft cock and balls through the damp lace!
I had an open invitation to return any night I had duty; I gladly informed her that I would have it again in about a month.
Oh yes… Tee was very special to me!
Source: reddit.com/r/eroticliterature/comments/9tksin/tee_nsfw_crossdresser_cd_mm_oral_anal
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