Rate by The Naughty Meter
Categories: Transvestites, Anal Sex, S-M / Domination / submissive
Tags: Anal Transvestite
Fulfillment: Act on it
WHACK! I couldn’t believe it but though it hurt so much I was actually raising my bum even more in the hope that she would do it again.
I had only gone to visit Charlie to get fucked, she was the only tranny I knew that would see me at such short notice, and I was so horny, I needed it so badly. I had spent the day before as an admirer, a gent in male form who has a love of trannies, fucking the ass pussy of my favourite girl, and she was having such a great time, unable to stop herself cumming as I pounded her from behind, that I realised I had to have some of that myself.
Charlie was available, I raced round, stripped completely, and then opened my bag, putting on my fishnet stockings, my cute but really slutty red and black lace knickers, matching bra and my favourite short red schoolgirl kilt. A long blonde wig, some falsies in my bra, mascara, eye shadow red lipstick was as far as I could get, Charlie was getting impatient. Lastly I slipped on my five inch heeled fuck me shoes and I was ready.
I sank to my knees in front of her, her lycra dress had ridden up to reveal her black sheer panties, and her growing erection. Gratefully, I pulled down those knickers, cupping her balls with the material, and rested my lips on her huge clit. This is what I needed, my lips opened, taking in her head, the taste divine, my tongue circling, my mouth sucking me all the way down, touching the back of my throat, her hands on the back of my head holding me there. I gagged slightly, but continued to suck her the way I knew she liked it, my hands travelling up to squeeze her nipples hard through the lycra. She gasped and released her hold, allowing me to fuck her clit with my mouth, up and down, sucking teasing, tongue twirling round the head, until eventually she pulled me away, saying she was getting too close and if I wanted fucking I’d better stop.
Still kneeling I crawled to the couch, and kneeling over the seat, buried my head in the leather and proffered my bum in the air for her. My skirt had ridden up exposing my bum, she pulled my knickers down, and of me, and positioned herself behind me. She then opened her bag of tricks and started to show off her collection of whips and crops, I couldn’t see but hear them swishing through the air.
“Have you ever been whipped?” she asked. “No, never I’m not into pain.” was my reply.
“Don’t worry, in the hands of an expert it won’t hurt, just sensitise you a bit. “
I was in the right position, so reluctantly I agreed to a try. At first she tried a short leather tassled affair, gently stoking my bum with it, slapping it gently, each time in a different place on my buttocks. No problems here, just warming me up for my fucking. Then WHACK! The pain was sudden and intense, but strangely pleasant, but before I could do more than cry out, another on the other buttock. Then once again, hard, then gentle strokes with the leather tassles and she was right my bum was so sensitive it did feel good. Her hand crept under to fell me incredibly hard, pulsating, throbbing like mad. I was so surprised, I had forgotten about my cock in the moment, certainly hadn’t thought I would be so erect.
Then her hand on my buttocks, caressing, lightly slapping, my bum so sensitive to the touch now. Then WHACK again, the tassles biting into me, but then I found myself pushing my bum higher in the air, wanting more, yet not, so weird an experience for me. A little bit of gentle tickling, my back arched, bum desperately reaching back, dreading but needing that next hard slap. WHACK! Oh so good, my hand slipped to my cock, how full he was now, I wanked him fast now, WHACK! Across the back now. “No playing with yourself! “ By now beside myself, my hands back in front of me, my bum and back being slapped hard then caressed, never knowing what was coming, total putty in her hands.
Then a finger up my ass, then two, I pushed back onto them, they plunged into me deep. Then out, I was stricken, until I felt Charlie’s thighs behind mine, her cock nudging my ass pussy, I arched still further, trying my best seductress moves, wanting so much the feel of her inside me. And then, joy, I felt her cock inch its way inside, spreading me, her hands round my hips pulling me back onto her. Then all of a sudden she was in, sliding all the way, the feeling exquisite, I was incapable of any thought other than Fuck me, Fuck me now, PLEEZE.
In and out, slowly, building up speed, my ass in the air, my hand now allowed round my cock, pumping furiously, all the time being mercilessly fucked by my gorgeous Charlie. I could feel her swelling inside me, hear her breathing quicken….”Take it all you cock sucking cum slut, take my big cock, feel her length pounding your little cunt”…., and then I could stop myself no longer, my cock swelled to enormous proportions, my hand flying up and down his length, and then the spunk rising,
Oh God I was coming at last, the first shot spat out the feeling so intense I almost blacked out, then again and again, I couldn’t stop myself, and I could feel Charlie’s cock inside start to pump her semen inside me, the picture of her emptying herself inside me drove me further over that edge, now a quivering wreck, but still cumming all over her floor.
Eventually, we both ceased, I was shaking for ages, but so sad to feel her cock shrink inside me, and pull out, wiping the excess spunk on my bum as she did so. Thank God I’d made that call, but how am I going to explain the redness on my bum when I get home???