First Fuck of a Beautiful Young TS

The gallery opening was not very crowded, so I quickly noticed the slender young woman examining one of the better paintings. She was of the type I find most appealing: small in physique, almost flat chested, with bright gray eyes and soft chestnut, slightly wavy hair below her shoulders. Her skin had a warm glow; her expression was serious, almost grave. She was dressed in a ribbed sweater and a simple skirt covering a trim bottom and slim, shapely legs in dark stockings.

We struck up a conversation about the art. She evidently had some knowledge and made some insightful comments about it in her low, husky voice. This and her lively, sensitive play of expression impelled me to invite her for a cup of coffee next door. I was pleasantly surprised when she consented, and was soon able to examine her from across a table as she sipped her cappuccino. She had told me her name was Emily. It was after a good deal of conversation that I understood -- in spite of narrow shoulders, slender, graceful hands, and virtually no adam's apple -- that she was not quite what I had at first assumed her to be.

My sudden realization must have been apparent, for she asked in a concerned voice if something was wrong.

"No, not at all...I just..."

"You thought I was a girl. Are you disappointed?"

"No." And indeed I was not. I'm in my late thirties: not conventionally handsome, but several others have been good enough to say I am easy on the eye. I'm of independent means through unearned good fortune, but try to give back, and stay busy, by volunteering and study. Apart from a couple of early experimentations, I don't have sex with other men; I'm not attracted to beards and hairiness.

But this was an exquisite creature, of androgynous beauty. Yet she appeared both shy and sincere; she projected a warmth along with a slight lack of confidence that I found appealing.

"No, really. Not at all."

We met twice more, for coffee and lunch in a pleasant bistro; she always offered to pay. She lived with her stepfather, she said; a shadow seemed to pass over her expression as she said his name. She had been "transitioning" for the last two years. With each meeting I found her/him more attractive and appealing. I was delighted when she agreed to come over to my condo the next week for carryout and movies; we shared similar taste in film. We kissed for the first time when we parted -- her soft, full lips felt wonderful, leaving me eagerly awaiting the proposed time alone with this very appealing young person

A soft knock came at my door; the doorman had called to tell me of her arrival. She was dressed as she had been when we first met, and looked exquisite. Her hair shone, her eyes sparkled; her teeth were white and straight, her breath fragrant. She slipped off her low heels; she was a head shorter than me; and we kissed gently.

It quickly became apparent that we had other things on our minds than eating Chinese carryout and watching Death in Venice -- a favorite of both of us. We sat on the wide couch and kissed with increasing ardor. She opened her mouth to me and her flickering tongue caressed mine. I sucked her sweet lips; the kisses intensified as we embraced, our breathing intensifying.

By now my cock had hardened inside my slacks, and I ventured to slip my hand under her skirt. Her thigh was silky smooth; I progressed upwards till I touched a firm bulge beneath soft panties. We commenced a mutual stroking that for me was intensely stimulating; Emily was also clearly becoming highly excited.

Slipping my fingers inside the leg of her panties, I felt her penis for the first time; an indescribable thrill. Its velvet smoothness and warmth increased my ardor even more; it grew appreciably as I fondled it. Her kisses became still more passionate; while she kept one arm affectionately around my neck, she employed the other to unzip my slacks, grope inside and release my pulsing cock from its confines. We continued to kiss and embrace as we fondled each other, delivering me intense pleasure; to judge from her sounds and throbbing dick, she wasn't minding it either.

Suddenly she broke off the kiss. Leaning into my lap, she pressed her lips to my cock's head, causing a near orgasmic thrill through it, then licked it teasingly. Parting her lips, she took the entire head inside her mouth and stroked it delicately with her tongue. Looking down at her slowly moving head, with its soft shiny hair and white, vulnerable nape was the most erotic experience of my life so far. She was stimulating the frenulum, that center of pleasure nerves, with a succession of lingual caresses; I could do nothing but groan in delight, which stimulated her to even more exquisite attentions.

But our position on the couch now meant that I had to relinquish my grasp on her own delicate shaft.

"Let's go in the bedroom." Just as well, since in another sixty seconds I would have exploded. And I like to make it last. We repaired to the darkened bedroom, and I turned down the sheets while she -- in spite of her delightful dick, that was how I thought of her -- slipped into the bathroom. A few minutes later, she came out, now totally naked.

In the subdued light Emily was a sight to be seen. Her breasts were only bumps, but had a beautiful softness and lovely nipples that perked upwards. Her belly was equally soft and appealing, but flat and fit. Her soft hair fell past her shoulders; her lips were parted in anticipation, I hoped, of a continuation of our previous activity.

Her body was smooth and shaved, except for a vee over her surprisingly large cock. The combination of her feminine beauty with her erect penis and tight ball sac was intensely erotic. She was smiling sweetly as she came into my arms, and pressed against me sensually, kissing me deeply as I stroked her long smooth back and caressed her small, soft, round bottom.

Then, feeling an unexpected bumpiness on her perfect buttocks, I glanced in the full length mirror and saw that that tenderest of skin was striped with pink weals.

"What happened to you?" I was shocked and indignant. Who had abused this sweet young doll so brutally?

"My stepfather. But I'll tell you that story later...please..." She fell to her knees and took hold of my rigid cock; I had taken my pants off, with no noticeable reduction in its horizontal condition. Stroking it tenderly, she opened her mouth and commenced to suck it again, this time taking it deeper and commencing a series of small sounds of enjoyment. I stood for a few minutes delighting in this fabulous sensation; my whole being was centered in my throbbing groin. Then with a great effort of will, I withdrew, picked her up and laid her lovely nude body, cock erect, on the sheet.

We lay entwined, exchanging kisses on each other's mouths, necks, nipples, fondling our cocks in tandem, pressing them together. Her warmth and fragrance were intoxicating, so that I kissed her the length of her flat belly for and the first time in my life took her beautiful, stiff, moist-at-the-tip cock into my mouth. She immediately reciprocated and we sucked each other slowly and deliciously.

Now as said, this was the first time I had had a dick in my mouth. But I'd had enough oral attentions from women, and seen enough porn videos, to be able to acquit myself reasonably. At any rate her moans and writhing seemed to indicate a satisfactory performance on my part. At one point she took me out of her mouth and I felt her tongue licking and probing my anus; a fantastic sensation. Then she resumed sucking my cock.

Did I feel gay, or perverted as I flicked my tongue around her unbelievably soft, cut head and took her entire length in my mouth, suppressing the urge to gag and causing her to utter a muffled squeal of delight? No; it was just an extraordinary extension of making love to a beautiful woman. Rather than experiencing any doubts, I redoubled my efforts to pleasure my exquisite partner, who continued to deliver the most wonderful sensations to my fortunate shaft.

Our mutual attentions created an electrical circuit of delight. Emily seemed to know exactly what pleased me, and the ecstasy she was delivering exceeded anything that had gone before. But it couldn't last. A surge of sensation drove through my shaft and I let loose an uncontrollable gush of come into her mouth, which she swallowed eagerly. A moment later, she ejaculated equally forcefully, and I gladly drank her salty essence. We slumped down in temporary exhaustion, moving only to realign ourselves and hold each other closely.

She rested her damp head on my chest, while I stroked her bare bottom, running my fingers down the soft divide. She squirmed pleasantly and pressed back against my exploring hand. I touched her tender anal bud, which felt unbelievably delicate; she pushed back harder and the tip of my finger slipped into her secret passage, which was as smooth as satin and which tightly gripped the intruding digit. She gave a long shuddering moan; I pressed in deeper. She reached down and gripped my cock; quickly she fondled it back into full erection.

Leaning down, she gave it a quick, delicious suck; then moved down the bed, raised her hips in the air, parted her legs and laid her head on the sheet. She looked back at me, her large beautiful eyes wide, inviting and submissive. The pink weals striping her beautiful bottom enhanced her vulnerability; her anus, fully in view, seemed to convulse. I knelt up; moved between her legs; and touching the head of my engorged cock to her winking entrance, slowly pushed inside, as her eyes widened and she gave a heartfelt sigh.

Her ass was tight and she cried out as I thrust deeper. Undulating her hips, she pressed her beautiful rear against me until my cock had entered her all the way. We froze in an exquisite tension, all of our consciousness focused on the joining of my cock and her ass. An amazingly sensual odor rose from her pores; I began a steady fucking of her ass, a series of three shallow strokes -- to stimulate the sensitive nerve endings at the entrance of the rectum, alternating with four deep strokes that reached to her innermost core, causing her to cry out each time I reached my fullest extension.

The slippery, sliding, perverse sensation was the most remarkable of my life; I fondled her stiff little cock in a reach around. She sobbed, moaned and writhed as I impaled her; an overpowering sensation was building in my groin, commencing at my balls and rising upwards. Her cock swelled under my fingers; a moment later she squealed in delightful satisfaction as her warm jissom poured over my fingers. I came furiously, deep in her sweet little passage, squirting an ocean of scalding come into her innermost, most sensitive sanctum. Then I collapsed on her soft, submissive, altogether delectable body, remaining inside her until my cock finally relaxed and slipped out of her, accompanied by a trickle of semen.

We lay hugging each other, exhausted and entwined, having the energy only to exchange light kisses.

"Will you tell me about this loathsome stepfather, now?"

"I've lived with him for the last year; my mother died a little while after they got together. Nobody knew she was ill. I had begun transitioning, and on my eighteenth birthday my stepfather told me I had to pay my way. He made me go and see a friend of his; a really horrible older man. When I wouldn't do the disgusting thing he asked, he complained to my stepfather, who made me strip and bend over. Then he caned me, hard. It hurt like mad; I think he was angry because the other man was going to forgive some money he was owed. My cousin lives with us too; she's transitioning as well, Clare, and he's just as beastly to her. You'd like her; she's littler than me, but prettier. We're afraid of him; he's violent and has some criminal friends, or says he does."

"Well, I have some powerful friends as well. They won't put up with any crap from your stepfather. We can easily protect you; they know how to deal with a prick like that. You know, Emily, I really like you. I have extra bedrooms here in the condo; why don't you come and stay with me for a while? No strings attached. Although you might bring Clare to visit; I'd like to meet her."

"Are you sure? I mean, we haven't known each other very long at all."

"Quite sure."