A Boy Whore's First Fuck

A Boy Whore's First Fuck

or, Turning Timmy

by Mistress Tawny Suede

I have had two significant interactions with Timmy Anderson.

The first one began with him turning to look at me and hesitantly saying, "Mr. Hagenauer, will you kiss me?"

I looked at him. He was dressed as a girl. Wig, makeup, a dress. He was not trying to pretend to be a girl. But he looked cute. I told him, "Sure, Timmy. I'd like that." But what I really meant was, in for a penny, in for a pound, I'm going to fuck you! Who looks a gift horse in the mouth? Not me.

I should back up and put this in context.

My name is George Hagenauer. I was a happily married man for several years until I started to get urges towards other men. I stepped out of the marriage bed a few times into the beds of some men of about my own age and found I much preferred sex with those men than with my wife. I eventually ran out of excuses for my absences and my wife divorced me. I still like her, as a person, but not so much as a bed partner. I've discovered I like my cock in an ass rather than a pussy, and I like kissing a partner while wearing a bit of leather.

My wife, Linda, got custody of our daughter, Mindy, who is in the final year of high school and will be going to college next year. I have visiting rights one evening a week, one weekend a month, and two holidays a year. But I have to promise not to have any men friends staying overnight when Mindy stays over. I bought a condo apartment a fifteen minute drive away since I did not want to lose Mindy from my life. Close enough I could get to her easily, but far enough away that neither she nor her mother might pop around unexpectedly and surprise me when my dick is down some guy's throat.

Timmy was the son of my friends Carol and Richard Anderson. I'd watched him grow up. There were several families in the neighbourhood with kids of similar age who all hung out together, or squabbled with each other - the kids I mean. The parents all got along fine with frequent barbecues and evening parties. Timmy had a couple of brothers and sisters who did well at school but Timmy was a bit of a disappointment. He struggled at school and was kept back a grade at least once. He was reasonably athletic, but shy, and he just didn't try. No university for that kid.

So when he asked me that question, I knew he was of legal age for anything I might want to do with him, or to him.

Timmy ended up sitting beside me in my car because my daughter had called me. I'd made a deal with her a long time ago. If she was ever out late and did not feel safe getting home on her own, she could call me and I would pick her up and take her home, no questions asked. It was Hallowe'en night and because of circumstances I do not need to go into I did not have any company that night, so it was easy for me to hop in the car when she called. Fifteen minutes later I texted her that I had arrived at the address she gave me, and a minute later she and two other girls came out of a townhouse. There was some jostling for position. Mindy dressed as Wonder Woman and Snow White ended up in back and the fairy princess was in the front passenger seat.

Mindy thanked me, but did not explain. She asked me to drop Joanne off first since she was on the way and then Timmy. "Timmy?" I asked and then took a closer look at the princess beside me. I had not seen Timmy in over a year but I did recognize him once he was addressed by his name.

Mindy explained that there were several guys at the party dressed in drag, but for some reason a group of guys had started to become hostile to Timmy so they called me.

"Are you okay Timmy? No one hurt you?" I asked. He muttered that he was fine, but he smiled at me. He liked that I was concerned. The three girls... well, the two girls and Timmy... all seemed a bit drunk, but no one was in danger of being sick, or so I thought.

We dropped Joanne off, but immediately after that I caught Mindy and Timmy exchanging a glance and then Mindy said she was not feeling well. "Drop me off next please, Daddy!" she said. "I think I might be sick!" I didn't know what she was up to, but I decided to play her game. I dropped her off and then started to drive Timmy home. He lived just two blocks away

But a block from his house Timmy asked me to pull over. He wanted to talk. As I stopped the car, he pulled off the wig he was wearing, and tried to wipe off his lipstick with a tissue. He got most of it, but smeared some of it around his chin.

He fidgeted for a moment and then said, "Mr. Hagenauer, will you kiss me." and he lifted his head up with his eyes closed.

"Sure Timmy I'd like that!" I said and leaned in, giving him a kiss on the forehead.

He opened his eyes, in frustration. And I saw he was about to cry. I took his hand and squeezed it, then I leaned in and gave him a kiss on the lips. He sighed, pulled back, then leaned in and kissed me harder. I could feel his tongue pushing and I opened my mouth slightly and let it in. We kissed harder and I sucked on his tongue and then he sucked on mine. Then he pulled back, and giggled, and rubbed his lip with his finger. "Thanks, he said" Then he added, "Your mustache tickles!"

"So what was that all about?" I asked him.

He looked at me. "Is it true? Well, I shouldn't ask that. I know it's true. I guess. You're gay, right? You used to like women, but now you like men? For, umm... for sex I mean."

I smiled at him. "For sex yes, I prefer men. But also for going out drinking, or going to a movie, or for holding hands on a moonlight stroll." I was choosing my words carefully now. Not wanting to chase him away, and not wanting him to have an excuse to quickly say goodbye. I needed him curious. As I said earlier. Once I decided I would kiss him, I had decided I was going to fuck him.

"Do you prefer men or boys, Timmy? To girls I mean." I was holding his hand and stroking the back of it with my thumb, slow circles. It always gets them.

"Um, yes, I think so. I like girls. Well, I'm supposed to like girls, aren't I? But when I look at other boys, cute boys, my heart starts racing. And when I see older men, I start to wonder what it would be like to snuggle up beside them. To have them put an arm around me. To... to kiss me. I don't know if I should say it, but my penis gets so hard when I think about a man holding me against his chest. I think I might die if that happened."

I started the car and pulled away from the curb. We went right past his house. "Where are we going?" he asked.

"I thought we'd go back to my place," I said, putting my hand on his thigh. "To test whether or not you will die when I put my arm around you, pull you close, and then kiss you."

"Oooooo..." Timmy moaned and he gripped my hand tightly.

"Did Mindy put you up to this, or did you arrange this yourself? You and me, in the car, alone?" I asked him.

"A bit of both. I told Mindy about my feelings months ago. Not about you. Just about boys. I figured she might understand, because of who her dad... who you... are. I don't know that either of us could say who got the idea first that maybe I could ask you to kiss me. But yeah, we did set this up, together. You don't mind?" Timmy admitted.

"Fuck no. You're cute. I don't mind kissing cute. If you want to neck for a bit that's fine with me."

I lit a cigarette and offered him one, but he declined. "Those things will kill you. And I'm told they taste yucky!" he said.

"The first couple, yes. But then you really enjoy it. Just like kissing a man. The first time you are uncertain, then you know you like it. Had you kissed a man before?" I asked him.

He looked down at our hands, and then back up in my eyes. "No never. That was my first time. And I did like it. And I only kissed a girl once before. I didn't know what I was doing and we bumped our teeth together, hard. She didn't want to do it again after that."

I parked in my underground garage and got out of the car. Timmy sat there for a minute. I looked back in and said, "Coming? If not, I can take you home." He hesitated a bit more and then got out, following me to the elevator lobby.

In my apartment I went to a drawer and pulled out a joint and lit it. I needed Timmy a bit more relaxed. "Have you smoked weed before?" I asked him.

He took the joint from me tentatively, then sucked on it, coughed a bit then inhaled again. "Just once. It was okay, I guess." It took a couple of minutes, but I could see him relax. I held his hand and led him around my apartment showing him paintings and knick knacks, and then when we got to the end of one room and we were turning back, I turned it into a little pirouette for him, and then pulled him close and kissed him again.

He returned the kiss enthusiastically and I held him very close very tight. I ran my hand up and down his back and then held it hard against his ass, pulling him against my groin and I could feel his hard cock and ground it with mine. He let out a soft oooooooooooo and almost collapsed. I led him over to the couch where we sat side by side continuing to kiss.

As we did, I reached for his groin and rubbed his cock through his dress. He moaned some more but did not stop me. So I bunched up his dress and reached underneath where I found his panties to be sopping wet. Yes, panties. No boy underwear under that dress. I reached my hand further in and grasped the bare flesh of his firm prick.

"Oh, Mr. Hagenauer! Oh, you shouldn't! No... please." But his protests were weak.

"You dress like a girl and ask me to kiss you. You accept an invite to my apartment and then you say no? I don't think so!" I said before I began kissing him along his neck and his jaw.

"Oh Mr. Hagenauer, that feels so nice!" he said. I wasn't sure if he was talking about the kisses, or my fingers teasing his cock. I stood us both up and quickly pulled his dress up over his head. At the same time I undid and kicked off my pants and then my underwear. Timmy's eyes almost bulged out when he saw my cock and he tried to step away from me. He was in much deeper than he had expected to be. I pulled him back, pushed him down on the couch and quickly got his panties off of him. His dick was a nice size and very wet.

He tried to get up, to get away, but I pushed him back again. Then I fisted his dick a couple of time before I moved my head down into his lap and I took his cock into my mouth. He tried to push my head away with his hands. "No, no, don't do that!" he protested. "I just wanted to try a kiss. I didn't want this... oooooo" Timmy trailed off as he lolled his head back. My tongue on his glans was feeling so good to him!

When I discovered I liked fucking a man's ass more than a woman's pussy, I also learned that I really liked having a dick in my mouth and over the years I had gotten very good at making men, and boys, squirm in pleasure. As I ran my hand up and down his slick cock, and twirled it around his glans, I asked him, "Has anyone ever sucked your dick before?"

"No never!" he replied and then pushed his hips up, encouraging me to continue. I could feel him trembling. I knew he would cum soon if I did not stop. And I had to stop. If he came, he would lose interest, and I would lose him.

"Have you ever sucked a dick?" I asked next as I sat up.

"No, never. I've never wanted...". he said. But I grasped his head in my hands and pushed his head down into my lap. My dick made contact with his lips. He opened his mouth to protest, but my cock filled his mouth and he sputtered. He flailed about trying to lift his head! I let him rise a teeny bit and then pushed him back down, letting my cock ride shallow and then deep into his mouth.

"You wanted to know what having sex with a man is like. Well this is part of it!" I told him. I pulled his head up, kissed him on the lips and then pushed his head back into my lap. This time he did not protest as my cock entered his mouth, and he settled down a bit. Soon he was slurping and sucking on my cock with no coercion from me. His hand took hold of my dick and he stroked me as he sucked. "Good boy!" I told him as I stroked his head. "Good boy."

He made contented mewling noises as he sucked me. He wasn't doing a very good job of sucking, but it was okay for a first unenthusiastic attempt. In time he would get better, if he decided to keep sucking dick. I suspected mine would not be the last.

I noticed that his free hand was wanking his own dick.

I wet my finger in my mouth and reached behind him and teased his asshole. His eyes opened in alarm and he tried to pull off my dick in protest, but I pushed his head back down until he started to choke a bit. He got the message. I slowly worked my finger against his pucker until I could get it inside him to the first knuckle. He again shook his head and this time managed to evade my hand. He rose up off of the couch and took a couple steps away, looking around, seeing what his option were for fleeing. He reached for this clothes, but that gave me a chance to grab him around the waist and lift him up. I threw him over my shoulder and carried him to my bedroom. His fists pounded on my back, but I ignored that, just as I ignored his crying.

"Mr. Hagenauer, no! What are you doing?!?" He cried out as I threw him on the bed, on his back. I reached into my side table and pulled out a bottle of lube.

"What's it look like, kid. I'm going to fuck you!" I said as I raised his ass. He squirmed and tried to turn over, to get away. I took hold of his legs and twisted him back onto his back, then I pushed his legs back so that his knees were near his ears. Ah, the flexibility of youth.

"I don't want to be fucked! You can't do this! All I wanted was to see if I liked being kissed by a man!" he protested. He looked fucking cute with tears in his eyes. But I would have fucked him even if he wasn't cute. At the moment, he was just a boy hole for my dick.

"You came on to me, remember? And if you run crying to anyone, remember Mindy knows that you were coming on to me. She'll tell whatever story I want her to tell!" I bent down and ran my tongue across his anal pucker. I swear, the damn thing winked at me, urging me on. I kept my weight on his bent back legs as I licked his perineum from that delightful asshole, up to his balls. I briefly took his hard cock back in my mouth and he groaned again.

But I wanted that asshole of his. I licked it again and then wiggled my tongue at the entrance and used my finger to again probe inside. "No, no," he protested feebly.

"So you're just a tease, is that it?" I raised my head and looked at him.

"What? No...!" he said, then gasped as my finger slipped further inside his ass. I wiggled it and he squirmed. "I... I just wanted to kiss. Really! I'm not... I don't know if I'm... "

"Gay?" I finished for him. "You don't need labels kid. You just need to lay back and enjoy your first fuck, because this IS happening. You want this. I can see it in your eyes. I can feel it in here!" I slowly thrust my finger in and out of his ass and twirled it. "Your mind may not know it yet, but your ass sure wants this. Your asshole is sucking my finger. It wants my dick and damn if I'm not polite enough to say yes!" I poured some lube along his ass and my probing got a lot easier. I then worked a second finger inside him. He groaned.

"It's starting to feel good, isn't it. Especially right... there." He moaned as I ran my fingers along his prostate. No man can resist a good prostate fingering.

"Oh god!" he cried out. "Oh yes, right there. Fuck Mr. Hagenauer."

"No, fuck YOU!" I grinned as I got to my knees between his spread thighs. I greased up my cock with more lube. The kid was going to be tight; they always are their first time.

"You liked the kiss, right?" He nodded at me as his eyes widened as my cock approached his anal pucker.

"And you liked me sucking your cock, yeah?" He said a quiet yes and shivered as I ran my cock head through the lube that coated his asshole. I pulled it back briefly and a string of cum connected my dick head with his pale star. I ran my fingers around that star and slowly pushed one inside. He was ready.

"And you liked sucking my dick?" He shook his head. "No" he replied! "I'm not gay. I just wanted to explore a bit."

"Well, kid, you're going to be fucked now. Welcome to being gay! This is going to hurt a bit at the beginning. Cry if you need to. The walls are thick enough you won't disturb my neighbours."

My first two pushes got me nowhere, but on the third attempt his pucker widened a bit and I breached his defenses. I kept up the pressure and my dick head slid into his ass. The brat did cry at that point. "Take it out! Stop! Don't do this!" he whined. Didn't he realize I was doing this for his own good? The kid clearly needed to be fucked!

I pulled back a tiny bit and then pushed in a bit further. Timmy threw his head back and cried out, "It hurts. Stop!"

"Just until you get used to it, kiddo." I said to him. He had stopped resisting me. His hands were splayed out on the bed, gripping the bed spread.

I pushed and pulled, thrusted and retreated for the next ten minutes, slowly working my cock deeper and deeper into his ass pussy. He wasn't the first young man I had fucked before anyone else, and he wouldn't be my last. I usually preferred someone more experienced and less resisting, but there was something special about being a boy's first fuck!

"Mr. Hagenauer, please.... "

"Please what kid? Let you go? Keep fucking you? What do you want?" I grinned down at him. He had stopped protesting about the pain in the last minute or so. I now saw the glazed look of pleasure in his eyes. Well, pleasure and weed.

"Please.... please fuck me! Oh god, I feel so full!" he mewled.

"Almost there, sport!" I told him. With a final thrust, I got the rest of my cock inside him. "Now you are truly fucked, Timmy. You're no longer a virgin. Or at least, you lost your ass virginity!" I wiggled my hips and he moaned as my cock slid around in his ass.

I suspected that after this fucking, he would never be looking to stick his dick in a girl. So that virginity would go untouched.

"That feels so... so nice!" he looked up at me, lust in his eyes. I released his legs. He lowered them enough to wrap them around my waist. He lifted his head and said, "Kiss me please!" I lowered my lips to his and we kissed hungrily as I began to pump in and out of his ass. I could tell you his ass felt like velvet as I slid in and out. But really, it felt like an ass. A delightfully tight boy ass, but an ass. It wasn't the best ass I'd ever fucked, but it was close!

I rolled Timmy over and put him on all fours at the foot of the bed. I stood behind him and slid my cock back into his ass. Smooth as butter now that I had opened him up. He turned his head to look back at me. He was panting, but his eyes were filled with lust. "Do you still want me to stop?" I grinned at him!

"No! Fuck me. Fuck my ass! Your cock feels so nice in there!" he grunted as he thrust his ass back at me. "Fuck me. Fuck me. Fuck me. Fuck me." he kept repeating. I reached my hand around and grabbed hold of his dick. He scrunched up his face and cried out, "I'm cumming!" As he pumped several strong ropes of cum onto my bed spread (shit, I should have taken it off of the bed!), his ass squeezed my cock tightly. I pushed fully into his ass and released my own jets of jizz into his ass.

"Oh fuck, I can feel you cumming in my ass!" he panted, his head collapsed onto the bed, his legs quivering from exhaustion. I fell onto the bed and my cock slipped out of his ass. He lay beside me, looked me in the eyes and said, "Mr. Hagenauer, will you kiss me?" Then he giggled, kissed my lips and then cuddled up to me, stroking my body with his hands.

We cleaned up and I drove him home. It was very late and so no one was looking as he gave me a long kiss before he got out of the car. As he was about to leave, I asked him, "So do you think you'll be getting fucked again soon?" He looked at me, shrugged and was gone.