Date: Wed, 8 Nov 2006 08:31:18 -0800 (PST) From: Wendi Robertson Subject: IN 1955 (TG) In 1955, just after my 18th birthday, I was hitchhiking in Pasadena along Colorado Boulevard. A man in a brand new 1955 Mercury convertible with the top down stopped to give me a ride. I hopped in the right front seat and we chatted a bit. He seemed quite nice. But, after a few blocks he started rubbing his crotch, and said, "Wow! I need a good jack off. Do you ever jack off son?" I got scared and made him stop and let me out. But, what if, instead, I had played along with him? Here is how I fantasize that it would have gone: "Gee, mister, this is embarrassing." "Well, do you like to jack off, son? I bet you do!" I held my head down, and said, "Yes, I do like to jack off. I jack off every day, mister." He smiled at me and said, "Let's jack off together!" With this he drove us to a secluded place in the foothills where he parked and put the convertible top up. He suddenly moved close to me, put his arm around me and kissed me full on my lips. This caused me to get very hard. I squirmed my ass on the car seat, which did not go unnoticed! He expertly unbuckled my belt and took down my trousers and shorts. He then fondled my very hard cock. He softly said, "You are so hot my sweet boy." With this he slid out of his trousers and shorts, exposing to my wide eyes a very handsome, very erect real-man's penis. His manly, very erotic, erect cock was so much larger than mine! I don't know why, but I suddenly felt like I was his girlfriend. I softly said, "I want your cock to rub against mine like I am your girlfriend!" "Oh baby, let's get in the back seat and be lovers!" He had a lot of excitement in this voice. We got in the back seat and both of us took off all our clothes. I lie on my back and spread my legs. He then mounted me and I wrapped my legs tightly about his ass, just like a girl would do! He put one arm around me and used his other hand to slowly stroke our cocks together! He then kissed me, with his tongue deep inside my mouth! I was a bit scared, a bit confused, but very, very excited! He whispered in my ear, "Do you wish you really were a girl?" I blurted out, "Yes! Very much so! I have worn women's clothes a couple of times and have loved it!" Oh fuck, honey, that is so hot!" With this he really began to jack our cocks together. He said, "You have such a small penis, dear, and you are small; you would make a wonderfully sexy sissy-boy girl!" I could feel my orgasm building and I had visions of being in his arm dressed as his special girl. I said, "I am going to shoot off, lover man!" He said, "So am I honey, let's shoot off together!" Suddenly, I had the most intense climax of my young life! It felt so good! It felt so good to be in his arms with my legs wrapped about him. As I shot I pressed my groin hard against his and I softly cried out, "Oh fuck, I want so to be your girl!" With this he said, "Oh fuck yes, baby, YES!" And, he shot a huge load of man juice all over my small cock and balls! He cried out, "Oh fuck, that feels so fucking good!" He slid his spent cock all over mine, slick with cum. He kissed me gently and said, "Let's go shopping for women's clothes for you honey. I am a Hollywood makeup artist. I know how to make you really look like a girl. You will be my sweet-sixteen very special girlfriend! I said, "I would like that.a whole lot! Will you teach me how to be your homosexual girl-like lover?" He kissed me some more and said, "Oh baby, yes, you will be my homosexual girl-like sissy in panties and girl's clothes. I will introduce you to taking my hard cock in your very hot girlish ass!" I shyly looked him in the eye and said, "My name is Wally but I want you to give me a girl's name." "Wally, my sweet boy, my name is Raymond. You shall be my very sweet Wendi!" Raymond drove us to the nearby Sears store where we had a most erotic and thrilling time buying me all kinds of women's clothes! While I was embarrassed, humiliated, yet excited during our shopping spree in the woman's department of Sears, he was very casual and so commanding about it all. He even held a couple of skirts and dresses up against me like I was his teen daughter being checked for the right size! All of this caused me to get so hard. He was quite hard, too. Raymond paid the sales lady while I stood there blushing furiously. She looked at me and then quietly said to Raymond, "Your young lady here will look very nice wearing these clothes for you, sir!" He looked at her, paused, then with a smile he said, "Yes, he really is a young lady at heart!" As we walked away I said, "I need to suck your cock right now Raymond!" "Oh, Wally, that is a wonderful idea. Let's find a men's restroom!" We found a large, quiet men's room. Raymond escorted me into a toilet booth and entered with me, closing the door. He whispered, take down your pants and put on these pink panties, and hurry, baby, because I am so hot!" I eagerly complied and soon had on the wonderful pink, full brief satin panties. My little penis was throbbing hard, encased in pretty panties where it belonged. I sat on the toilet as Raymond unbuckled his trousers and lower them and his shorts, exposing his wonderful, very erect penis to my wide eyes. Whispering very quietly but with much lust in his voice he said, "Suck my cock panty sissy! Suck it now darling sissy boy!" "Oh Raymond, yes, I am a teen girl and I love you!" I then kissed all over his balls and licked up and down his rigid cock shaft, working my tongue into his cock slit. "Oh baby, that is good.very good! You were born to wear the dress and suck the cock!" He became quite excited and gently, but firmly shoved his cock into my mouth as he took my head into his hands. He was in complete control and starting fucking my mouth like it was a pussy! "Oh fuck, sissy baby, take my cock in your mouth pussy! Take my cock sissy darling!" he softly whispered in a very lustful manner. My little rock-hard penis was flat up against my tummy inside my pink panties. I lightly and rapidly rubbed it like it were my clitoris as I eagerly took my darling man's thrusting hard cock inside my mouth pussy! I whimpered softly like a sissy must when taking his man's cock! "Oh fuck, sissy baby, take it! With his he gave my mouth short, fast strokes and his cock exploded a flood of semen into my sucking mouth. I eagerly swallowed all I could, but some ran down my chin as my dickette exploded in a most intense jack-off cum! My cum simply soaked the front of my panties all over! Raymond leaned back against the booth door exhausted. I leaned forward and kissed and licked his spent penis all over. I looked up at him and said, "Darling, I am your special girl! I love having you cum inside my mouth in public!" He softly replied, "Seeing you in panties excites me so much Wally, baby!" We came down off our mutual high, got dressed and quietly departed the store. We stopped at a drug store. I waited in the car while Raymond bought cosmetics for me. I still wore my pink panties under my trousers and relished the sticky feeling of my drying cum, which was caking the panties and making me feel so deliciously girlish and quite queer. I loved feeling queer this way! Shortly, Raymond and I were in an expensive hotel suite where he spent hours dressing me in fresh panties, a tight girdle, sheer nylon stockings, a lacy full slip, a padded satin bra, a blouse, a nice skirt, and high heel shoes. He made my face look like a hot girl's but he decided against my wearing a wig. I looked so cute and so queer! I was a cute teen boy all dressed so pretty as a girl and with lots of girl's makeup on my face, but my short boy's haircut showed unmistakably that I was a boy. Soon, my darling Raymond took me all the way as he expertly and so gently introduced me to the ultimate joy for which I was truly intended; as a boy woman with my manly lover's hard cock deep inside my anus! He had me dress for bed in a sexy garter belt and sheer nylon stockings, no bra so he could suck on my nipples, a pink satin short baby doll night gown, and no panties! He said, "Lie on your tummy sissy and let me prepare you. Relax my sweet lover and trust me completely." He took a generous amount of some kind of lube and slowly worked it into my ass with his finger. I got so hard as he did this and I thought my little penis, which was flat up against my tummy, would just spurt all over the bed right then! I squirmed my buttocks and pushed myself back on his finger while I made little sissy moans. (Wow, it felt so good to feel my little cock rubbing on my satin night gown!) "Oh baby, you want it really badly, don't you sissy boy?" "Yes I do Raymond; I feel like the girl I really am meant to be!" With this he teased his hard cock head all over my buttocks. I whimpered more and said, "Oh darling Raymond, make me your wife!" "Yes baby, yes!" He pressed his cock against my anus and very slowly slid inside me. He took a lot of time, making sure it wouldn't hurt me. He really knew what he was doing. Inch by inch I could feel him enter me, until his balls were resting against my little balls. He was still and he leaned down as kissed me on the back of my neck. He said, "You are now mine, sissy boy, and I love you more than a man loves his female bride!" He then playfully, gently bit on my ear lobe. What a masterful lover! "I am going to start screwing you now, darling. Let me know if it hurts." He started with slow, small thrusts. It was wonderful! I moaned in a high-pitched sissy voice, "Oh Raymond darling, do me honey, do your sissy-boy girlfriend!" "I haven't ever been this excited Wendi honey! You are a wonderful sissy!" With this he started to thrust a bit faster. I moved my ass back against each of his thrust. I knew I was meant to be an effeminate, transvestite sissy for a real man like my wonderful new friend, confident, and commanding lover! "Does it feel good baby?" asked Raymond. "Oh yes, yes, it does.faster and harder honey!" He increased his tempo and the sound of his groin slapping against my ass cheeks, along with the bed springs squeaking, now filled the room. He began to chant, "Oh, yes, yes, yes, oh, fu.fu.fu.fu.fuck baby, take my cock!" I felt so sexy, so demure, and so submissive. I was now pinned under the constant onslaught of his rapid and deep thrusts. I was simply now his feminine vessel for his urgent manly needs. And, I loved yielding and submitting my body to him, to be his sexual conquest, to be his, to take his wonderful, urgent ejaculation just like I were a hot young woman giving her vagina to her man! I cried out, "Honey I am going to shoot on the sheets! Eeeiiiii yes!" "Oh yes sissy cunt lover, cum for me.cum for me! I flooded the sheets with my intense spurting of sissy cum as I felt his short strokes flood my boy pussy with his man seed! I was so in love with him!