Her name was Samantha, but everyone called her Sam. She was a petite, preoperative trans girl, slightly older than I was. After weeks of flirtatious online chats and photo exchanges, she invited me over to her apartment one Saturday evening. I dressed in my favorite pair of jeans, sans underwear for a touch of daring, and rode my motorcycle to her place in the city.
As I arrived, the apartment was dimly lit, setting a sensual mood. It was one of those open plan apartments with only one room, the bedroom, lounge and kitchen all sharing the same area. Sam excitedly welcomed me in, wearing a stunning skimpy pink dress that hugged her body, and I could just make out her sexy black lingerie beneath. The mood was a mix of sexual excitement and tension as we sat on the couch together. She wasted no time in unzipping my jeans, letting out a gasp of pleasure when she found me without underwear.
With a wicked grin, she knelt down in front of me and took my already semi rigid shaft into her mouth, sucking gently around the head. Her skilled tongue sent waves of pleasure surging through my body as she worked my rapidly hardening member. She continued to deliver a master class in fellatio, alternating between sliding my cock deep into her throat and concentrating her efforts around my sensitive head for about 10-15 minutes. Before she suggested that we move to the bed on the other side of the room.
I quickly removed my shirt, slipped on a condom and sat on the edge of the bed watching as she seductively peeled off her little pink dress, letting it drop to the floor, exposing her sexy lingerie covered body, an exquisite black satin babydoll top with a very small sheer black satin g-string bottom that struggled with all its might to contain her now raging cock. I relaxed down onto the bed on my back as Sam slid off her little black g-string, adding it to the dress pile on the floor before climbing onto the bed, and straddling me in the reverse cowgirl position, directly over my condom covered cock.
I was very impressed at her preparation before I arrived, as she never applied any lubricant after I arrived at her apartment. She confidently gripped my cock, guiding it to her tight, pre-lubricated asshole. She let out a long moan of satisfaction as she impaled herself on my hard member. The feeling was extremely intense, with her anal walls squeezing my rock hard rod. Propping myself up on my elbows I decided to reach around to play with her wonderful cock, which is something that I love to do during anal sex, but she playfully pressed my hand away as she wanted to be the one in control of providing all the pleasure this particular evening. I took the hint and laid back again as I proceeded to focus on watching her gorgeous heart shaped bum sensuously rolling as she continued to expertly ride my manhood, steadily working it from the tip almost slipping out to balls deep inside her.
The sensation was unreal, her ass hole was like a vise clamping around my pole. She had already worked me up with the amazing blowjob earlier, that left me nearing the edge of my ejaculation. Now, with her bouncing on me, her passionate moans filling the room and hearing her sultry words saying: “Oh fuck babe, your cock feels so good in my little pussy” I was quickly losing this battle against the pleasures of my own body. I grabbed her beautifully toned hips, desperately trying to slow her pace and extend the ecstasy of this sexual encounter, but she was relentless, as she rode me harder and faster. It was too much for my heavily aroused body to withstand and within a few minutes, I felt the familiar twitching in my penis and proudly announced that I was cumming, as I thrust hard up into her I proceeded to empty a massive load of cum deep inside her magnificent tight little hole.
She slowed down with her ass still gripping me as she glanced back, with a satisfied grin. When I pulled out, she didn’t miss a beat, sliding down to kneel between my legs. I removed the condom and her tongue flicked out, lapping at the cum still clinging to my softening cock, her lips wrapping around the tip she attempted to work me back to fully erect as we both wanted another round, but my body was not playing ball, and despite her efforts she could not get me fully hard again.
After a while, she sat back on her heels and we decided to save it for next time. The night ended there, although it was a pleasant ride home without underwear and the warm night air stimulating my content but still semi hard penis. When I arrived home I got naked and stroked my cock cumming hard again with the mental images of our earlier sexual activity fresh in my mind.
Sam and I chatted several times after that glorious evening and we were planning to hookup again, she wanted to help me practice to last longer during anal sex so that we could both enjoy it more and more. However shortly after that I started a fairly long term relationship with a lady and after that relationship ended I was unable to get in touch with Sam again to arrange another sexy play time.
