Lonely Sissy in School Holiday

I am a 16 year old male student and I am also a gay sissy. I was adopted before I was 5 years old and I was brought up be two maiden ladies. I was brought up as a girl from a very early age! When I was twelve I started to see my breasts developing and they were feeling quite sensitive to my touch, this also made my small penis get aroused and I felt different.
When I reached 14 I had developed breasts, my penis was bigger but sadly I was being rejected by both boys and girls and bullied by both.
During the next two years I became a true sissy and flaunted it as I felt I had nothing to lose!! I did well academically, was good looking as well as rather pretty, slim with long legs. My aunts who were rather wealthy bought me nice underwear and fashionable trousers, dresses, blouses and skirts so I looked nice.
To the present: I was sitting on a bench in our local park three weeks ago when a man sat down on the bench. I noticed him glancing in my direction several times. I felt naughty so I crossed my legs showing a lot of my thighs, he started to talk to me, asked my age and so on. I answered in a rather flirty voice and then he moved closer and shocked me by saying, "are you a boy?"
I stammered "I'm both and I like it". He said "well so do I, you look lovely, what are you doing for the rest of the day?".
He seemed to be in his late fifties or even sixties, nice looking and spoke gently, so I thought there was not much risk and answered "nothing, why do you ask?" He said I would like to show you my house and spend the day with you, would you like that too?" I answered "well ok, how far is it from here?", "not far" he said, "we can walk".
He had a large house, surrounded by a big garden. He opened the front door and let us in. Once in the hallway he closed the door and turned to me and said "can I kiss you?", "if you want" I said, "I do" he said and he took me into his arms and kissed me passionately. It felt good, I felt wanted for the first time, I responded with my kisses, I felt myself backed up against the wall with him thrusting against me, his hand went under my skirt and into my knickers, his touch was electrifying, he knew what he was doing. I opened my legs, "not yet" he said, "lets take our time, we've got all day, so lets go and have a drink, chat and get to know each other". I felt really good, really girly and really wanted and I felt different in a nice way!!

If you want to hear what happened next, please post a reply.

1.9 years ago

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    • Well darlings, We went into the lounge and I sat on the settee while Jack went and got us a drink each, he brought them in, gave me mine and then said he would only be a minute as he wanted to change into comfy clothes.
      I was feeling so aroused sitting there caressing my penis trapped in my silky knickers, that I pulled the hem of my dress up above my knees showing the sexy lace trim of my satin slip.
      Then jack came down the stairs, he had put on a silky paisley robe just tied in the front by a loose belt. As he walked I could tell he was naked underneath and the robe bulged where he had an erection. "You look lovely" he said "please stand up my darling" and he came over to me, took me in his arms and kissed me so passionately and lovingly that I responded and pushed myself against him.
      I could feel the size of his erection, I lifted my dress and slip and with my other hand reached beneath his robe and folded my fingers around his member. I drew it between my legs, OMG! it was big, it reached between my legs and right to my knicker clad bottom and it was so stiff!!!!
      I kissed him and said "please take me to bed Jack" and Jack responded with "I would love that Oh! lets go". We rushed up the stairs with Jack right behind me gently smacking my bottom under my dress. He led me into the bedroom, we kissed again, I undid his robe and let it fall to the floor and I could see his penis jerking with passion and excitement, I turned him around sat him on the bed and got down on my knees, drew his foreskin back and kissed his beautiful penis running my tongue up and down its shaft.
      Part 2 in a moment or two.

    • Part 2 darlings,
      After a while Jack said "let me take your dress off sweetie" and we stood up, we were so close, his aftershave smelt gorgeous, he turned me around and slowly ran the zip of my dress down to my waist. I felt so sexy, I was nearly cumming in my knickers, he gently slid my dress off and I stepped out of it. I stood there in my slip, knickers, bra and stockings as he laid it over a chair, he turned around, "Oh! Wow!!" he said "my darling girl" and he took me in his arms a laid me on his bed.
      He laid beside me, we were kissing, he had his hand in my knickers caressing my penis, "don't cum to soon sweetie" he said, but his kissing and caressing nearly brought me to climax several times. I wanted him to fuck me, "and don't you cum to soon Jack because I want that lovely penis in my bottom" I said.
      " You are a naughty girl, have you ever been fucked before" he said, "no I answered, but I want you!!! Jack put his hand under my bra, "Oh! you have real breasts" and he slipped them out and kissed them gently, I was nearly out of my mind with desire as he played with my nipples "Oh! fuck me Jack, please , please" and he got off the bed and came back with some body lotion.
      "You will need this" he said and rubbed some on my anus and onto his penis. He put me onto my back, my legs in the air and got behind me. I could see his penis jerking, I put my feet over his shoulders and he put his finger into my bottom, the feeling was fantastic, then more fingers, I lifted my hips up, he slid a pillow under me, "this will hurt a bit at first" he said, "but I'll be careful.
      I felt his hot penis head against my anus, I tried to relax, there was a sharp pain then another, I had my hands around him trying to pull him closer and then suddenly he was in me "OMG! Jack" I screamed as he thrust "Oh! I love it, I love it" I shouted and I was his little girl.

    • If you want to hear the ending let me know.
      Signed: Jacks naughty little girl.

    • OOOOOOOOHHHHH!!!! You made me cum reading about you and Jack, please tell more.

    • Part 3:
      Jack was so gentle, trying not to squash me as he fucked me. I just loved watching his face contort with desire and pleasure at what he was doing to me and he was so big, I couldn't believe that I was taking that huge penis inside my bottom. My knickers were getting wet from my own excitement but I was trying so hard not to cum.
      I loved the way he was kissing me as he thrust into me bringing himself down to my face with passionate kisses with his tongue, Oh! that tongue, it was like a reptile in my mouth, twisting and turning as his penis pushed deep inside me.
      I couldn't hold my cum any longer, Oh! Jack I screamed I'm cumming, I'm cumming, "cum my darling" he said "while I'm fucking you, I want to feel your cheeks clench" and I released my cum, he pushed down on me trapping my penis in my knickers, I thought I would never stop cumming, "my darling, my darling" shouted Jack as he pumped his cum into me "oh! you lovely girly and your all mine, all mine" he shouted.
      We lay there panting, then he slowly moved back, took my penis out from my knickers kissing and sucking it, "lovely sweet cum my darling" he whispered "and your still stiff you naughty girl, I'm going to smack your bottom" and with that tucked my penis into my knickers, lifted me off the bed and laid me over his thighs. He pulled my knickers tight across my bottom, tucked his own penis into the front of my knickers and proceeded to smack my cheeks. I liked it!!!! I loved it!!!!!!
      Jacks penis was erect again, I could feel its hardness against me, "Oh! no more smacking Jack, Oh! fuck me again please, please!!" and this time as we stood he bent me over the side of the bed, pulled the gusset of my knickers out of the way and pushed into me. OMG! what a feeling. "You naughty girl, you naughty, naughty girl" he shouted, smacking my cheeks as he thrust.

    • Please!

    • Omg yeah tell more i'm not a sissy but i am gay

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