tagTranssexuals & CrossdressersTrained by the Neighbors: Seduction

Trained by the Neighbors: Seduction

bybottomsatx©

I'd always been small for my age, a trait I inherited from my mother. She was positively tiny, and I barely reached her height and didn't grow much more beyond it. While it made her indescribably cute, being so small didn't fit me as a male.

My father left when I was still in second grade and mom married Jim, my step-dad, just before my 12th birthday. If she was tiny, he was huge...at least, compared to us. He was just over six foot tall, and very broadly built. The difference in their height made it almost comical to watch them walk together, holding hands. It looked more like father and daughter than husband and wife.

Even though I wasn't his biological son he spent a lot of time with me, mainly just hanging out. I thought it was because he wasn't able to father a child of his own due to an injury early in life (but that thought turned out to be wrong). He was very strict with mom, however. You could sense that he loved her deeply, but he almost controlled her every move. I assumed that was because of the big difference in their ages, since he was about 12 years older than her.

They were good friends with the neighbors. Sam and Debbie had lived in the neighborhood before we moved in. They had a daughter who had moved away to college, and now it was just the two of them. Sam could have been Jim's brother: They had the same build, the same mannerisms, liked the same sports teams, and got along famously. Mom and Jim spent as much time over at Sam's house as they did at ours.

One Thursday after my 18th birthday, I heard mom and Jim arguing about something. I couldn't tell what it was, but it was surprising for mom to argue with Jim at all. I could tell that he won the argument when I heard mom calm down and go back to her normal meek voice. Shortly after the argument, Jim came to my room and told me that he and Sam were taking Friday off to fix Sam's fence, and that they needed me to stay home from school and give them a hand.

We went next door about 7AM the next day. Mom disappeared into the house with Debbie, and the three of us began tearing down the old fence and putting up the new one. To be honest, I wasn't much help. Either one of them could carry more lumber in one trip than I could in four, so eventually my task was to hold boards so they could nail them in place, and run into the house to get them beers.

It was a hot day, and Sam declared a stop for the day around 2PM. All three of us were hot and sweaty, and we grabbed the shirts we'd taken off earlier and went inside. I didn't see mom or Debbie, so sat on the couch next to Sam and Jim popped into the kitchen and came back with three beers. I was flabbergasted when he handed one to me, but he told me that I'd done a good job and was just as hot and sweaty as they were. I wasn't, but I'd never had any alcohol of any kind before, and wanted to try it.

Jim and Sam watched me as I drank my beer. My small size, my empty stomach (we'd worked through lunch), and my inexperience with alcohol made it go straight to my head. I finished the first and a second magically appeared in Sam's hand. Jim and Sam just grinned at me when my speech started slurring and my eyes glazed over a bit while I drank the second beer.

By the time I had finished the second beer, I was really woozy. So woozy, in fact, that I could have swore that I saw Debbie come out of the bedroom stark naked, walk to the kitchen, then return to the bedroom. I didn't say anything, and Sam acted like nothing ever happened. I looked around to see if Jim gave any indication of seeing what I saw, but he was nowhere to be found. I had almost convinced myself that I was seeing things when she came back out of the bedroom, still nude, and walked towards the couch that Sam and I were sitting on.

Debbie is about 8 years older than mom. The most charitable thing you could say about her face would be "harsh". In more blunter terms, she's almost ugly. However, she had an absolutely perfect body. She had a slim body with large, well rounded tits that didn't sag very much at all for a woman in her 40's, perfect belly, long legs, and a nice bubble butt. As she got closer, I saw that her pussy was shaved.

I shifted uncomfortably, as my dick was growing in my shorts. I'd only seen two women nude in my entire life. I accidentally walked in on mom while she was getting out of the shower once, and just recently, Jim had left a porno magazine on the kitchen counter that I found. Both times, my dick grew and I had to masturbate to make it go down.

Sam leaned over, put his arm around me, and whispered "She's fucking awesome, isn't she? Damn, I'm glad I married her." My dick was twisted in my underwear and was becoming almost painful as it got harder. I tried to be sly about moving it to a more comfortable and less obvious position, but the beer had made me clumsy and it was obvious what was happening to me.

Debbie saw it, and giggled. She walked up to me, her large breasts swaying with each step, and said "Poor baby. Do you need some help with that?"

I was shocked when she dropped to her knees in front of me, unzipped my shorts, and fished my dick out. I tried to stand up, but Sam's arm was still around me. Before I knew it, she'd slid her mouth over my cock and started sucking it.

God, it felt fantastic....MUCH better than when I jerked off. Her mouth was warm wet velvet, and her tongue was doing wonderful things to the bottom of my cock. While her mouth was working magic on my cock, Sam's hand slid down and started toying with my nipple while his other hand stroked his cock. The combination of her mouth and his fingers proved too much, and I started cumming, shooting wad after wad of cum into Debbie's mouth.

Debbie looked up at me and pulled my cock from her mouth. Using one finger, she pushed what little cum had escaped her lips back into her mouth, and said "Mmmm...yummy." She rose, letting her tits slide up my legs and belly, and kissed me. I could taste my cum on her lips, and I didn't care. I was so relaxed from the orgasm and the beer that it didn't matter.

When the kiss broke, she stood up and stepped back. Sam was still playing with my nipple and stroking his cock. He said "Well, now we have a problem. My wife gave you a blowjob and since I should have gotten it, now you owe me one. Fair's fair, right?"

In my half-drunk, orgasm relaxed state, it made perfect sense. Debbie pulled me up, helped me take my shorts and underwear off, and maneuvered me between Sam's legs. Debbie pushed down on my shoulders, and I dropped to my knees. Sam's cock bobbed in front of my face.

Debbie kneeled down behind me. I could feel her tits pressed against my back as she whispered into my ear. "Go ahead, suck daddy's cock. I'll teach you how."

Sam slid his hand around the back of my head, and gently pulled my face towards his cock. My mouth opened of it's own volition, and the head of his cock slipped between my lips. Slowly, he pushed his cock into my mouth. I didn't know exactly what to do, but the act was making my dick hard again.

I inexpertly moved my mouth up and down his cock, mainly at his urging. Debbie kept up the encouragement, telling me how I should move my mouth, how much I should take in, to take it out of my mouth and tongue the head of his cock. I wasn't doing a good job, however, and eventually she told me to move over and nestled in between Sam's legs with me.

She told me to watch her, and then began sucking Sam's cock in earnest. After a minute, she told me to try it. I did my best to copy her moves, and was rewarded with a slight moan from Sam. We traded off with her sucking him and showing me how to, then me trying it. Sam was enjoying the hell out of it.

Debbie told me it was her turn again, but this time she was going to bring him to the edge. "I'll get him ready and you can make him pop. Make sure you swallow all of daddy's yummy cum." She took his cock back into her mouth and really worked it, her head bobbing up and down as Sam started breathing in short shallow gasps.

I missed the signal that Sam gave Debbie, but suddenly she pulled her mouth off of his cock, and forced my head down onto it In a second, my mouth was being flooded with shot after shot of Sam's cum. Instinctively, I swallowed and swallowed and swallowed. Even half drunk, I loved it. I don't know whether it was the taste or the act, but I knew it was something that I wanted to do again.

Sam eventually subsided and started softening, and his cock plopped out of my mouth. "Good girl!" Debbie exlaimed, "Isn't it yummy?"

I started to say that I wasn't a girl, but she stood me up, turned me around, and kissed me deeply before I could get the words out. I could feel Sam's hand cupping my asscheeks while Debbie held my face and shared Sam's cum.

"C'mon," she said, "Let's let daddy recover and go do girl stuff." She grabbed my hand and led me off to the bathroom.

Again, i started protesting about being called a girl, but she ignored me. Once we got in the bathroom, she told me to start the shower. I refused, and told her that I wasn't a girl. She grabbed my shoulders and looked me in the eye. "You just sucked a man's dick, baby girl, and from what I could tell, you liked doing it. Let's be honest...you don't have the body to be a man. I think you'll make a much better girl than a boy."

The alcohol was wearing off, but her words did make some sense. I would never be "manly", I was too small for that. Plus, my dick was small. I would measure it as 5 inches, but an inch of that was vanity. Add on top of all that the fact that I did love sucking Sam's cock. My shoulders drooped as I realized that she probably was right.

"Don't feel bad," she grinned, "we girls can still play. I'll go down on you if you go down on me. Now start the shower."

Feeling defeated by the realization, I started the shower. We both entered it, and she washed me while I washed her. I loved washing her tits. Things started happening faster now, and I couldn't keep up to protest.

"Ok, lets get rid of that nasty hair and make you smooth like mommy," she said, grabbing a razor. I wasn't sure what hair she was talking about until she lathered up my pubic hair and drew the first stroke with the razor. I wasn't very hairy at all, with no arm or chest hair, and very little leg or pubic hair. In a minute she was done and my groin was hair free.

She showed me how to shave my legs, and we finished showering. After we dried off, she told me to wait while she went to get something. In a minute, she was back with a nightgown. "It's my daughter's that she left when she went to college," she explained, slipping it over my head. "It'll probably be big on you, but it's all we have until we can go shopping."

I didn't understand the "shopping" part, but the nightgown felt awfully good on me. It was very silky and sexy. She caressed my body through the nightgown, and the sensation was indescribable. She said "I bet Sam is going to love sliding his dick into your tight little ass," giving it a squeeze.

I gave a start when she said that. "Oh, yes," she said, running her hand through my hair. "Daddy is going to fuck your hot little ass, and if you're good, mommy will suck your dick afterward. Now hold still." She started applying makeup on my face, telling me "Make a kissy face" when she put lipstick on me. In a few minutes, she was done and stepped back away from me. "How do you look?" she asked, proudly.

I looked in the mirror and saw a pretty girl looking back at me. Mom was really modest with makeup since she really didn't need much to be beautiful, so I'd never seen anyone wear very much. It was a bit on the slutty side, I thought, but that made it even the more exciting. I said, "I DO look like a girl, don't I?"

Debbie kissed my cheek and said, "A very pretty one, I think. Let's go see if daddy thinks so too."

She put on a robe, and led me out of the bathroom by my hand. She led me back into the living room, where Sam still sat on the couch, and presented me to him. "Taadaaaa!" she said, moving behind me and urging me forward.

"Wow," Sam said. "You're a hot little bitch, aren't you? Come here and let daddy have a better look." I could see his soft cock twitch, waking back up.

The alcohol was rapidly wearing off, and I was starting to feel more self-conscious. My head bowed and my hands covering my crotch, I stepped forward. Sam grabbed my hand, and pulled me into his lap. "Very nice," he murmured, running his hand over me.

He began kissing and nuzzling my neck while one hand stroked my nipples and the other caressed my ass. I instantly got hot, my little dick tenting the nightgown. His hand turned my face towards him, and his lips pressed against mine.

As he kissed me, he slid his arms under me and stood up, carrying me. The kiss broke, and my arm went around his shoulders as he carried me to the bedroom. Once inside, he laid me on the bed and then laid down on top of me. My legs spread of their own volition, and I could feel his hard dick pressed up against my inner tight as he kissed me again.

Sam kissed me again, then began to kiss and suck on my neck. He then pulled the front of the nightgown down and started licking and sucking my nipples. A voice in the back of my head said "so THIS is foreplay!", but it died down as his mouth excited me more. My dick was ready to explode, pressed up against his belly through the nightgown. As his mouth left my nipples, he said "You're very pretty, but you need MUCH bigger titties, girl."

Debbie came into the bedroom and dropped her robe. She sat on the edge of the bed, leaned over and started kissing me while Sam moved off me. I laid there, accepting her kiss and returning it. I could feel Sam move around on the bed.

Debbie broke the kiss, took my dick in her hand and started stroking it, and asked me "Are you ready for daddy to fuck you?" I hesitated, and fear made tears well up in my eyes. "I don't know," I stammered.

Debbie leaned over and gave me a quick kiss. "Don't be scared, baby girl. It'll hurt a little bit at first, but it will end up feeling wonderful." Her hand kept stroking my dick, which had started to go soft because of my fear.

Sam was laying on his back, with his cock doing a flagpole imitation. It was all wet and shiny from a lubricant he had in his hand. He motioned me to get up, and got onto my knees. He spread the lubricant all over my asshole and crack, then told me to straddle his legs.

"Sit on my cock, baby," he said. I sat down and his cock was nestled in the crack of my ass. Sam laughed and told me, "No...sit on it so that it goes in your ass."

I slowly raised back up, and Debbie took Sam's cock in hand. She lined it up with the bud of my asshole, and pulled me down by the shoulder. His cockhead pressed against my asshole, then slowly began spreading it open.

"OW...IT HURTS!'' I cried. Debbie let me move off his cock until it was only pressed against my asshole. "It will at first, but remember that it'll feel very good later," she said.

I moved back down until his cockhead started spreading me again. Again, the pain hit, and I cried "OW!" again, and pulled back up. I tried again, only getting a little bit further than before before the pain hit again.

Looking back, I realize that Sam and Debbie were using incredible patience. Every time Sam got a little deeper into my ass, I would cry out and pull off. After about five minutes, Sam's patience ran out.

"Oh, goddammit...." he said, frustrated, grabbing my hips and shoving his whole length into me. The pain was incredible, and I started crying.

"Quit being a crybaby," Debbie said harshly. "You're ruining your makeup. If you don't stop right now, there'll be no blowjob for you, missy."

I tried to stop crying, but the pain was intense. Slowly, however, I felt a warmness that wasn't associated with the pain in my ass. My ass was getting accustomed to his cock, and Debbie's promise was starting to come true. Sam's patience had returned, and he didn't move his cock inside me at all, letting my ass stretch around him.

I sniffled, my tears stopping. The warm good feeling was getting stronger, and the pain was lessening. I raised my ass off his cock a bit as an experiment, and the pain twinged, but it wasn't as strong as before. In fact, it felt really good to feel him move inside me. I lowered myself until my asscheeks were resting on his groin. It was starting to feel really, really good.

"That's my girl," Sam said. "Bounce a little bit on daddy's cock." I raised again, pain even lesser, and ground my ass back down. I almost liked it, and ignored the pain. Raising and lowering again, the pain was almost gone and the warm good sensation was almost as strong as the pain was earlier.

"Mmm, take daddy's cock," Debbie murmured while her hands moved from my shoulders to my nipples. She started kissing my neck as I grew bolder and my ass started bouncing on Sam's cock faster.

After a few minutes of riding his cock, Sam said "Are you ready to be truly fucked like a girl?" I nodded, very much in the throes of lust. Without pulling his cock out, he rolled us over and pulled my legs up. It wasn't very comfortable, but I didn't want his cock to pull out of me.

Sam pulled his cock almost all the way out, then slowly slid it back in. I gasped, the sensation was incredible. He increased his pace, and within a few minutes was slamming his cock into my ass. I loved it...I wanted it...it felt so good and so right. My arms went around his neck and I tried to pull him closer to me and deeper in me.

Sam's face started to turn a bit red, and he slammed himself into my ass deep. I knew he was cumming in me, and I wanted to milk every last drop from his balls. I ground my ass against his crotch.

Sam's orgasm wore off, and he collapsed on top of me. He gave me a deep kiss, then pulled his cock out of my ass. I felt a raw sensation now that I was too turned on to notice earlier, and I felt his cum fall out of my ass and run down the crack of my ass to pool on the bed.

He rolled off of me, laying next to me. "Jesus, that was the tightest ass I've ever fucked," he panted. Debbie laughed and said "Better than mine?" He laughed with her and said "This little girl has a lot to learn before she's as hot as you, baby...but damn that's a tight ass."

Debbie helped me up and led me to the bathroom. She told me to clean myself up, clean off my makeup and then handed me a washcloth. "Get this wet with warm water and go clean daddy up." I did as I was told, Sam caressing my shoulders as I washed his cock off.

Sam dozed off, and Debbie led me to another bedroom. "This was my daughter's room. It's yours now. I already let your folks know you'd be staying here tonight. They said they'd come by tomorrow and see you."

My own dick was still rock hard, pushing out the nightgown and I glanced at it. Debbie gave me a disapproving look and said "No, nothing for you. You were a bad girl, crying like that and ruining all the makeup that mommy gave you. You can jerk off later." She rummaged through the drawers and found another nightgown and a pair of panties. "Change into these...that nightgown is all sweaty and has some cum on it."

I changed as told to, then Debbie told me to get in bed. She spent the rest of the evening teaching me how to lick pussy, orgasming several times. She let me masturbate while sucking my nipples. Finally, she got out of bed, gave me a quick kiss, and told me to go to sleep. As she was walking out of the bedroom, however, she stopped.

"You're a girl now," she said. I nodded. "Well, now you need a girl's name. What name would you like?"

I thought for a second. Debbie knew that this was the last step of turning me into a girl. If I picked a girl's name, then I would identify myself AS a girl.

"Mindy."

Report Story

bybottomsatx© 6 comments/ 55782 views/ 14 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartjt789, bigbearcouple and 12 other people favorited this story! 

Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous04/05/14

loved this sexy story wish some one would fuck me while dressed as agirl ilike sucking cock

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 6 User Comments  or
Click here to leave your own comment on this submission!

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel