My Gay Sissy Life

I have told you all before that I am a gay male sissy. I have been dressing in girls, then ladies clothes since I was a young boy. I have cultivated my appearance to that of an attractive woman and have even developed my breasts to a lovely sensitive 38B.
I am wealthy enough to buy myself the most sensual lingerie and sexy floaty dresses. I live on my own and have three married boyfriends which visit me regularly for sex. I also have girlfriends who help me with my make-up and my hair style. I love how I look, it never ceases to make me aroused, especially when I pull my French lacy silk knickers up over my stockinged legs.
My home is in a small town in the UK with shops and several pubs. The staff in my local pub know me and are very welcoming. Its where I met two of my boyfriends, James and Brian. My other boyfriend is an elderly neighbour who approached me one day at his garden gate, his name is Jack.
They are all turned on by the way I dress and are particularly attracted by my large penis when we are making love. Old Jack is the most enthusiastic and he is well endowed and likes to take his time with me. He loves buggering me when I'm in my knickers and stockings, but he also likes getting naked himself and then slowly undressing me, pushing his erect penis against the skirt of my dress and then hugging me when I am down to my slip, he just loves the feeling of silk or nylon against his skin. He tells me that he remembers how ladies used to dress years ago when he was young, all stockings and suspenders he says. I think he is secretly in love with me, he is so gentle and caring, we kiss and caress for an hour or more, whispering sweet nothings, rolling around either in or on top of the bed until I take him inside me, feeling his foreskin pull back against the lips of my anus as he pushes his lovely penis into my bottom.
Jack has so much sexual energy and he lasts longer if I get on top and ride him. He loves that position because he can kiss my breasts and play with my knicker clad penis and he adores it when we cum together and I cum over his belly, he is so naughty and sexy.
Signed: Jasmine


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  • I'm in the midlands sweetie x

  • I live in the uk also , I would love to meet up with you somtime sweetie x

  • Please tell me what part of the UK you live in darling as I would love to meet you.
    Signed Jasmine

  • Jack phoned me, he wants to come round tonight the naughty boy, as his wife is going to bingo. He said he wants me to dress in white lingerie with a white silky floaty dress or skirt and its lucky because I have a very flirty silky Coast skirt, very full and sensual, I can't wait to wear it for him!!
    Signed: Jasmine

  • Please tell me more Jasmine, I love what you tell us.

  • Well darling I've been given a right good seeing to!! I got home early from work, showered, shaved all over, body creamed and went into the bedroom and curl dried my hair so it fell into curls around my face.
    I went to my knicker drawer and pulled a white full suspender on together with a pair of nude silky shiny Pretty Polly stockings. Then found a pair of white silk lacy high cut French knickers and pulled them up over my erection. A lacy white bra came next, feeling so sensitive against my nipples. Then I went to the wardrobe and selected a beautiful vintage lacy white full slip that had so much cream lace I nearly fainted as it slipped over my head and down my thighs I was so aroused. I found my chiffon black see-through blouse and then the silky full chiffon Coast skirt and pulled that up over my hips tucked in my blouse and fastened the skirt with the hook and eye clasp and zipped it up.
    I stood in front of the full length mirrors, I have six of them. Wow!!!! I looked fabulous a lovely sexy lady even without my make-up!!!! Jack will love this and lifted my skirt to see, Oh! yes, 1950's silky flirty sexy and I did a little twirl admiring how the full skirt flew up revealing my underwear. I could also see my lacy covered breasts under the black chiffon blouse, beautiful!!
    After applying my make-up, I waited for Jack to come round.
    More later, signed Jasmine.

  • My door bell rang, I peeped out and of course it was Jack. I let him in and closed the door, I was trembling as he walked around me, then he took hold of me and kissed me, "give me a twirl" he said and I pirouetted on the spot holding his hand for balance. "Jasmine you are lovely and I can imagine what you are wearing under that skirt because I can see some of them beneath your blouse" and with that I watched his hand reach for my breasts, "lovely, lovely" said Jack "now some play acting, go into the kitchen while I take my clothes off and stand at the sink pretending to wash up". I left him and minced into the kitchen on my high heels and stood at the sink. Shortly I felt him behind me, "oh! you naughty boy what are you doing" I said as he pulled me close with one hand on my breast and the other lifting my skirt, I could feel his erection, "Jasmine spread your legs, I complied and I felt his hand pulling my knickers over, spread my cheeks and then his penis pushed into my bottom. I screamed as I felt it go right in, I clutched at the sink, Jack's other hand left my breast and with both hands lifted my skirt up over my waist as he held me.

  • Part 2:
    OMG! he was randy and said as he was thrusting "I've taken a Viagra can you feel the difference Jasmine?" I stuttered "yes Jack you feel bigger and stiffer darling" and with that he thrust even harder "I love your stockings and silky knickers Jasmine" and I said "don't cum over my dress you naughty sexy boy lets go into the bedroom I'm uncomfortable" and I felt his penis pull out of me. I patted my skirt down "you are really naughty Jack that was almost rape". "You are so sexy Jasmine, I'm sorry" said Jack "but I just had to have you there" I replied "your forgiven and I liked it although it was a bit of a shock".
    We went into the bedroom and Jack was fumbling trying to unfasten my skirt, I did it and gathered it up and while I was picking it up bending down naughty Jack was on me again, "your beautiful silk slip darling" and I felt him pushing against me, then I undid the buttons on my blouse and slipped it off and stood there in my underwear and high heels. Jack sat back on the bed, took my hips in his hands and pulled me to him. He caressed my erection, lifted my slip and placed it over the head of my penis, I was so very aroused that I thought I was going to cum as he took me in his mouth, "gently, gently" I moaned "don't make me cum to soon darling". His hands were on the cheeks of my bottom caressing, pulling me towards him, I could feel his huge erection against my stockinged legs so I closed my legs trapping his penis.
    "Bed!!" said Jack and he stood up pulled the duvet back, pushed me down and then he was on me lifting my legs pulling my knickers aside and he was inside me. OMG!! what a session.
    Signed: Jasmine

  • Part 3:
    Jack fucked me every which-way, I loved it, what stamina he had and that Viagra gave him an enormous erection. Jack's hands were all over me, caressing, feeling, thrusting, I thought his penis was going to penetrate my heart it was so far inside me, OMG! how long can he keep going.
    I don't really know how long he fucked me, because I was so light headed that I nearly passed out several times, I do know however that he had me screaming as he bit my nipples as he was thrusting. I had my legs wrapped tightly around his waist when he ejaculated, my slip was over my head, my bra was up off my breasts and my knickers, lord knows where they were, but Jack leaned forward, he was up as far as his penis would reach moaning into my neck "Ohoooo! Jasmine, Jasmine, Jasmine hold me ,hold me!!!" and with several enormous thrusts Jack's cum shot inside me, "don't let me go Jasmine darling I think I've got more Ohooooo! I have, I have" and I felt his penis swell even bigger, OMG! his cum was pumping out of my bottom there was so much.
    I held Jack closely for several minutes, I could feel his penis pulsating, throbbing he was sweating and then he rolled off me. "Oh! Jasmine that was fantastic, wonderful, you sexy darling in your sexy undies, you naughty girl" and with that Jack kissed my breasts, slid down the bed, took my penis in his mouth, licking all the cum off that I'd spent while he was fucking me and brought me to another amazing ejaculation.
    I'm looking forward to when Jack comes back tomorrow.
    Signed: Jasmine

  • Part 4
    Jack can't get enough of me, he is visiting me three or four times a week, I'm sure now he is in love with me.
    He told his wife he was going fishing when she went to see her sister yesterday (Sunday) but as soon as she had left he was round knocking on my door.
    It was only 9.30am and I was still in my negligee and knickers, but he came in, stripped off and dragged me to bed. We were under the duvet in seconds and I could feel his huge erection between my legs. I straddled him, felt him pull the gusset of my French silky knickers aside, I reached behind me and fed that erection into my bottom.
    I leaned forward kissing him, telling him to be slow, OMG! he was so big and I was adoring his hands caressing my breasts. Jack told me I was a naughty girl, I felt like a naughty girl as I clenched my buttocks trapping that lovely cock.
    You want my babies, said Jack and that really turned me on, I was long stroking him, nearly letting his cock slip out before pushing down again.
    Jack was moaning with pleasure, Oh! I love what you can do to me Jasmine and I replied, but you know how much I adore your penis you naughty boy.
    Then Jack turned me over, my negligee was up over my breasts, I wrapped my legs around his waist, he kissed my breasts and began his marathon Fuck. OMG!! he could go the distance, he thrust that erection into me, up and down, up and down his hips went, I gripped his bottom cheeks pulling him down and then releasing them as he withdrew.
    He lifted my legs higher as I knew he was about to cum, I felt him shudder, then final short thrusts as he unloaded his cum, his babies into me. Jack was exhausted, he rolled off me and we laid side by side kissing, he was still semi hard and I gripped his penis between my legs and we fell asleep.
    Signed Jasmine

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