This story is a work of fiction intended for adults only. It tells the tale of a young man who discovers a new life as a transvestite when he moves out of home. Please read the first three parts so you can fully appreciate the story.
All feedback is appreciated - email me: spaceboy_4192@hotmail.com
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Amy's New Life: Part 4 by Spaceboy
"You look like you've never been kissed before," Robert said, gently.
"I... haven't," I whispered. "I mean... I have, but... not by a guy."
Without saying a word, he took my hand and lead me over to the deckchair. Robert sat down and stretched out along the full length of the chair. I bit my bottom lip as he motioned for me to join him. Slightly unsure of what he wanted me to do, I perched on the edge of the chair next to him, before he quickly grabbed me around the hips and pulled me up onto his body.
Now I was lying on top of him, my head level with his and my little stiff cock pressing deep into his hard stomach. He kissed me again, cupping the back of my neck with one hand while squeezing my ass cheeks with the other. Feeling his hairy chest with my fingers, I kissed him back with more passion than before, moaning quietly as I did so.
He pulled away from my mouth and held his middle finger up to my lips. Recognising the cue, I licked it at first then took it into my mouth, sucking it slowly as he moved the large digit back and forth. The subtle flavour of the sweat on his skin had my saliva glands working overtime. He was delicious.
As he withdrew his finger from between my lips, we resumed kissing. I felt his hand return to my ass, but this time his spit-covered finger crept underneath my thong and traced a moist path between my cheeks. When he reached my tender hole, I tensed up, grabbing a handful of his chest hair.
"Just relax, sweetie," said Robert, kissing me softly on the forehead. "I'll be as gentle as can be."
His finger circled my hole, easing me open ever-so-slightly with the aid of my own saliva. I pushed back and felt the tip of his finger pop inside me. I shivered. Robert was looking directly into my eyes now. I nodded acquiescence and his finger slid deeper into my ass.
Once he'd entered as far as the second knuckle (no more than two inches), he pulled back and began to work up a steady but slow rhythm. My moans grew louder as he finger fucked me. Almost without thinking, I started grinding my cock against his stomach. The twin pleasures in my ass and on my cock were more intense than anything I'd ever felt.
"Baby, you're so hot," Robert encouraged me. "Daddy loves your tight ass."
Daddy? My cock spasmed as he uttered that word.
"Let me taste it," said Robert, although he didn't wait for permission. He half picked me up as he sat up, then placed me down on my back. He gripped my legs under the knee and lifted my ass into the air. Now holding my g-string aside, he licked from my tight balls all the way to my hole.
I felt his tongue prise me open once more. Just as it had tickled my face when we had kissed, I could feel his stubble rubbing against my smooth ass cheeks. It felt so good. His tongue continued to work my hole, sending shivers of pleasure throughout my entire body.
Soon his tongue was replaced by his finger, only this time the extra lubricant meant it slid in with ease. His fingered fucked me faster, harder and deeper, massaging my prostate with every movement. My moaning grew louder and louder, just as my breathing became shorter and shorter. Moments later, one... two... three spurts of creamy cum shot from my cock and landed on my tummy.
I looked down at Robert to see his face break into a wide grin. His finger still motioned in and out of my ass, but much slower now. I didn't want him to ever stop.
"I'm thinking that's the first time you've done that, too," he grinned again.
"Uh-huh," I replied, too high and out of breath to speak properly.
"Well, I feel honoured to be your first. And it looks like you enjoyed it."
"Oh, I did. That was... amazing."
Robert slipped his finger out of my soaked hole and readjusted my g-string. "Perhaps there's more I can teach you as well."
I nodded in agreement, straightening out my legs and half sitting up.
He chuckled. "Can I get you a tissue?"
"Oh! Yes, thank you. There's a box in the kitchen."
While Robert went inside, my thoughts immediately turned to what else he could possibly teach me. Does he want to suck me? Does he want to have sex with me? Can I really have sex with a guy? Of course, he'd just fucked me with his finger, but his cock would be so much bigger. His cock... oh please, I thought, please let me see his cock tonight.
Robert returned with the tissues and also another drink for each of us. He waited for me to clean myself up before joining me on the chair. We both lit cigarettes and sipped on our drinks.
"So tell me how long you've been dressing like this."
"Uh... about four years, I think."
"How old are you now?"
"20. My 21st is in a few weeks."
"Damn, now I feel old!"
We both laughed. "I'd guess you're mid to late 30s?"
"Close. And thank you for being polite. I'm actually 45."
Okay, I thought, that makes him older than my Dad. Which means he wasn't wrong when he said Daddy before. And what does that make me? His son? Or his daughter?
We chatted through another few cigarettes and at least one more drink. Robert told me how he'd been married - twice - before realising he wasn't really cut out for that sort of lifestyle or commitment. When his second marriage ended three years ago, he had moved into this apartment on his own and decided he was simply going to enjoy himself. He'd had dozens of sexual partners since, mostly women but increasingly more and more men, especially boys around my age.
As we continued to chat, I found myself again lying on top of Robert, running my fingers across his chest as he held me in his arm. My thigh rested against his groin and I could feel the heat and shape of his cock through his jeans. I told him about my ex-girlfriends and how my sexual relationships had been incompatible with my desire to dress as a girl. The correlation between my lack of interest in sex with my girlfriends and my fascination with the men I saw in porn was very high.
Now thoroughly at ease in Robert's embrace, I looked up into his eyes and said, "You know when you said Daddy before...?"
He nodded.
"Well... I... liked it."
I felt his cock stir against my thigh.
"So... can I... call you Daddy?"
His cock moved again, growing harder and beginning to press into my leg.
"Babe," he said, planting a big kiss on my forehead, "Of course you can."
I smiled and held him close. Subconsciously, I think, I began massaging his groin with me thigh.
"Hmm," Robert grunted, with obvious pleasure. "I'm wondering if there's anything else Daddy can teach his daughter tonight."
I drew a sharp breath at the way he emphasised the word "daughter" and my cock went wild, instantly returning to full erection.
"Kiss my chest," Robert urged. I did, relishing the sensation of fur and muscle against my face. "Lower..." I ran my tongue down his torso, my hands clutching at his sides. "Lower..." I had reached the top of his jeans. This was it. All I could see was the large bulge of his cock straining against the denim.
Robert stroked my hair, encouraging me further. My nervous fingers clumsily undid the button before hesitantly sliding down the zip.
"You are wearing something under here, after all," I teased him as his open fly revealed boxer briefs. Outlined by the white cotton was his thick piece of meat. Gingerly, I touched it, tracing its curved length with my fingertips.
Robert tucked his thumbs under the hem of his boxers and pulled them down, the quick release causing his cock to spring up and slap against his stomach. He slid his underwear and jeans down so I could see the entirety of long shaft and large, hairy balls. He was clearly much bigger than me, almost twice as long and twice as wide. His uncut foreskin was thick and bore pubic hair from about halfway along its length before matting around his low-hanging balls.
"Have you been this close to a man's dick before?"
I shook my head slowly, reeling in awe at what had just happened. The heat and musky smell rising from his crotch was intoxicating.
"Touch it."
As my hand wrapped around his shaft I was surprised to discover it was too wide for my fingers to meet my thumb. I slid his foreskin down to reveal the blood-red head coated in glistening pre-cum.
"Taste it."
My nostrils filled with his scent as I edged closer. My tongue flicked out, licking the large drop of pre-cum that was leaking from the slit before tracing a circle around the head. Growing bolder, I opened my mouth wide and slid my lips down over the entire head. So soft and yet so hard, I couldn't believe how incredible it felt, nor how delicious he tasted.
Glancing up at Robert, he smiled down at me then placed his hand on mine. "Use your hand while you suck. Like this."
Soon I had synchronised my mouth and hand motions, going down when I exposed the head then pulling back to let my hand bring the foreskin back over the glands. As I built up a steady rhythm, I could hear Robert's breath begin to get faster. His hand moved to the back of my head, clutching my hair to push and pull me up and down.
I was sucking his cock. My first ever cock. I felt so submissive, on my knees between his legs, my bare ass poking out and totally exposed to the night air, my lips and hand wrapped around the first real man's cock I'd ever seen. I wanted nothing else than to please him. To please "Daddy". I was loving it. I didn't want it to end.
Suddenly Robert's thighs tensed underneath me and he quickly wrapped his other hand around mine, his large fingers grasping his cock tightly. A few swift strokes later and he came, a thick rope of cum shooting straight up and into my waiting mouth. Instinctively - or was it his urging behind my head? - I took him back between my lips as another two then three streams of cum hit the roof of my mouth. As he relaxed I gently ran my tongue over the head, extracting every last drop of semen before swallowing.
"Come here, baby," Robert said as he pulled me back onto his chest and wrapped me inside his arms. He touched his finger to my chin where some of his cum remained and held it out for me to lick. I swallowed again, savouring the sweet taste.
"Looks like you've enjoyed tonight's lessons," he said, caressing my naked thigh.
"You're a good teacher," I replied, cirlcing his nipple with my finger.
"And you're a fast learner!"
I blushed. Resting my head once gain on his firm, hairy chest, I reflected on how comfortable I now felt in his presence. Could this man really be my "Daddy"?
"You look tired, sweetheart. I'm thinking we both should be getting some sleep," said Robert.
"Mmmm..." I made sure he could see my pout of disappointment.
"Oh, don't worry, there'll be plenty of time for more of this in the future." He lifted me up as he rose from the chair, then paused to tuck his now flaccid - but still huge - cock into this boxers and readjust his jeans.
Robert leaned in once more and kissed me. "Thank you for a wonderful evening."
I went to bed that night with the taste of his cum still on my tongue.