tagTranssexuals & CrossdressersJulian Falls in Love

Julian Falls in Love


My name is Julian, about 5' 8", slightly built, and with long shoulder-length brown hair and rather effeminate features. At school, I was what you would call a loner. I was shy and lacked the confidence to approach girls. However, I did develop an interest in the clothes they wore. The girls looked so good in their short, pleated grey skirts, black tights and light blue blouses. As time passed, my desire to dress like them grew ever stronger.

I think my interest in girls' clothes really started one day when, aged fourteen, I was left alone in the house while my parents and sister were away visiting relatives in another part of the country. I was rummaging about in my sister's wardrobe and found her underwear. Trembling with excitement, I undressed and put on some panties, stockings and a white slip. Immediately, I had an erection. I had to masturbate several times to relieve my feelings and wore the underwear all day, savouring the unaccustomed softness and lightness of the material against my skin.

At first, I didn't consider myself gay, but gradually my masturbation fantasies changed. From imagining I was having sex with girls I knew at school, I began to picture myself dressed as a schoolgirl and being undressed then penetrated by a man. These feelings remained entirely private. I felt so frustrated that I couldn't carry out my wish to dress like a girl, although I did send away for several pairs of panties from a mail-order catalogue and wore them from time to time whilst masturbating.

I left school at 18 and started a job at a firm of architects. To take my mind off the lack of love in my life, I started to go running long distances and became quite good, athletics being my favourite sport. I would even go running in my lunch breaks in the local park. It was there I had the encounter that would change my life.

I was jogging around the park, when I heard someone call out to me. I couldn't see anyone at first. Then I heard the cry "over here!" I walked down a grassy incline in the direction of the voice and saw a man sunbathing out of sight of the public. He was naked apart from a pair of underpants. I recognised him as the personnel manager from my workplace. He was in his mid-thirties and was a friendly sort. I walked over to him and he asked me if I wanted to take a rest, which I was glad to do, since really it was far too hot to run. I was amazed he had the nerve to lie in a public place in just his underpants! We chatted for a few minutes and I felt strangely comfortable with him. He seemed a really nice guy, not to say good looking. I couldn't help but notice his well toned body, the result of many sessions at the gym. But he was not overly muscled. He was also refreshingly forward - after a while I was astonished to see him remove his underpants. He lay there, stark naked! He also asked me to do the same, but all I would take off was my top. I remember blushing when he said I had a lovely slim body. For the next few days, I met him at the same place, sunbathing as it was a particularly hot summer, and we got to know each other really well. One day he asked me if I would like to go for a drink. I fancied him like mad and readily agreed.

I met him after work at a pub near his house. I didn't drink too much because I was trying to stay fit. However, even after a couple of glasses of wine in that blazing heat, I felt light headed and I lost my inhibitions. He invited me to his house for coffee before I headed home and I thought why not? We got to his place, which I was very impressed with as it was so clean and tidy, and sat on the sofa to watch a comedy video. The video was absolutely hilarious, especially in the slightly inebriated state I was in, and I felt utterly happy to be in Lawrence's company. At some point, he placed his hand on top of mine. It was as if electricity were running through my body. He looked me intently in the face and asked if he could kiss me, and I said yes. We kissed passionately as he held me closely in his strong arms. After a while he got up and said "I have a little film I think you'll appreciate!" He picked a DVD from his collection and put it in his player. I sat on Lawrence's knee and watched transfixed as two gorgeous boys made love. After undressing and french kissing one another for some minutes, one bent over the arm of a sofa and allowed the other to penetrate him. The active partner was thrusting really hard as he neared climax, so much so his thighs slapped against his lover's buttocks. They were both moaning passionately. After a few minutes, the active partner ejaculated inside the other. I had never seen anything so erotic.

He asked me if I would like to come upstairs. I smiled at him and replied "I wouldn't mind."

He then commented "but I'm old enough to be your father."

"I don't care," I replied. He led me by the hand and led me upstairs to his immaculate bedroom, where he put on some soft music. I started to take off my clothes but he stopped me and said he wanted to undress me himself. Very slowly and deliberately, he unbuttoned my shirt then unfastened my trousers.

But I had forgotten that I was wearing panties, the only article of women's clothing I dared to wear in the office! "So do you wear these normally? he asked."

I felt my face go all flushed as I shamefully admitted "I would wear a lot more given the opportunity." To my relief, he smiled and didn't seem to mind at all. With obvious relish, he lowered my panties to my knees then sat me on the edge of the bed. He knelt on the floor in front of me and began to kiss and lick me between the legs. He really took the time to make me feel good and I felt gratified that he complimented me on the smoothness of my skin (for some time I had been shaving my pubes off completely). Eventually he took my erect penis in his mouth. It felt wonderful. Very quickly I could contain myself no longer and ejaculated into his mouth.

After kissing and caressing for a few minutes, he was hard and ready for me. He made me kneel on the bed whilst he explored my anal opening with his fingers, but decided I was just too tight to enter and he didn't want to hurt me. He brought a bottle of baby oil from the bathroom and I wondered what he had in mind. Pouring some into his hand, he rubbed it all over my thighs and belly. "Lie down, and keep your legs together," he ordered. After I did so, he lay on me and began to thrust his penis in between my lubricated thighs. He was very gentle and loving, and kept kissing me, telling me how gorgeous I was. After a good ten minutes of this 'frottage', Lawrence groaned and came profusely over me. He then sat me on his knee whilst he kissed me deeply and masturbated me to another climax. I curled up in his arms and slept like a baby. We made love again in the morning. I felt wonderfully secure and happy in his bed.

Before I left, Lawrence gave me an anal vibrator, which he encouraged me to use. It was uncomfortable at first, but I learnt to relax my sphincter so I could get it inside me. It felt highly pleasurable. I was determined to give my lover the maximum enjoyment the next time we had sex.

We arranged to meet the very next weekend, where Lawrence said he had a surprise in store for me. I was intrigued. On arriving at his house, we kissed. "Your surprise is in my bedroom," he said. "I think you're going to like it." Walking up to his room, there were several bags on his bed. I couldn't have been more excited by what I found. There were some bra and panty sets, as well as several pairs of tights; two mini-skirts; an assortment of pretty blouses, and a pair of heeled sling backs. He had even provided a bag full of make-up - lipstick, mascara, eye-shadow and the like. I hurriedly stripped off and put on a grey pleated skirt, white knee socks and white blouse, with white cotton lacy panties and bra underneath. I did the best I could with the make-up, knowing little about it. But I felt deliriously happy. The whole of my body was tingling.

Checking myself in the mirror, I thought I didn't look too bad and rushed downstairs. I flung my arms around my lover and thanked him for making my dreams come true. I would have liked him to take me there and then, but he said "slow down, angel, let's just take our time!" We had dinner and shared a bottle of wine, then curled up on the sofa to watch a film. It was a delicious evening. Finally, it was time for bed. Putting his arm around me, Lawrence led me to his room. We kissed passionately on the bed, whilst his hands reached up beneath my skirt to fondle my bum through my cotton panties. I responded by feeling his rock-hard cock, which was making an unsightly bulge at the front of his trousers.

"I think I'm ready to go all the way tonight, darling," I said.

"Good girl," he replied. It was so thrilling to hear him referring to me already as a girl!

Lawrence undressed and, as he lowered his boxer shorts, his cock sprang up and slapped against his belly. Evidently, he needed no further stimulation. I started to take off my clothes but he stopped me. "You look fine just the way you are," he whispered. He lay on his back and beckoned me to sit down on him with my back to his face. Taking a tube of lubricant, he hitched up my mini-skirt, tucked the hem in the waistband, lowered my panties and applied the lube liberally to my opening. After slipping on a condom, he said "just take your time, angel, and if it hurts too much, just stop, OK?" I grasped his cock and eased it into me, trying to relax and pushing as if I were attempting a bowel movement.

After several minutes of trying I got it halfway in. "It doesn't feel too bad, darling," I said.

Gripping me tightly by the waist, Lawrence turned me on my side and began to thrust, at first gently but gradually with more vigour. It was still a little uncomfortable but it was so good to know I could pleasure my lover in this way. His thrusting became increasingly urgent and I sensed he was about to come. "Oh angel, you make me feel so good!" he groaned as he lost control and exploded in orgasm inside me. It felt tremendously gratifying that now I could fully explore my femininity with this gentle and loving man.

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