The (slight) Feminization of Tommy Ch. 03

Story Info
Role playing comes with a cost. We need to talk.
1.9k words
4.53
5.1k
3
1
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Corjix
Corjix
182 Followers

Here is the third chapter of: The Slight Feminization of Tommy.

This is a gentle and kind story of two young men having their first time - together. The emotions and sex are really sweet, and fun, and fine. If you are looking for something more hard core...please keep looking. All are welcome to read.

********

"Tammy? Really?" I thought I would do anything to keep my boyfriend Buck happy...but now, for the first time, I have some doubts. With his nut starting to subside, and his breathing starting to return to normal, Buck sees the way I feel. I've stopped riding his cock. He's still inside of me, though. Hey, at eighteen, we both stay rock hard even after we cum!

"Uh, it just slipped out." His puppy eyes don't work on me this time.

"You called me Tammy, Buck. I can do this dress up for you. I can wear the panties, the earrings, even the lipstick. Hell, the perfume you bought is wonderful! But it's my name, Buck. My name is Tom. Tommy. Not Tammy."

"Sorry."

I suddenly realized that I want Buck to want ME...not some distorted idea of his about being with a 'girl' so he does not have to face his truth about being gay. All through high school I had this fantasy of being with Buck. It was no secret that he played the part of the jock...and I was the introverted nerd. But this hurts.

"I won't do it again." He is looking at me with a serious face. No. This whole dynamic is not good. Not for me; and not for any future we may have together.

"Look, Buck..." I'm slowly pulling off of him, and standing on the floor, looking down at my naked boyfriend. "...Role play can be fun, but not if it's used to hide behind. Roll over, lover. You said I should fuck you, and I'm ready." I have been taking off the earrings as I stand and talk with Buck. These tissues are removing the lipstick. "We might use this stuff again, Buck. But right now, if you're ready, this man is going to take your cherry ass for a ride. This man will pump his cock deep into your hole. This man is going to fill his boyfriends ass with a big hot load of milk. You ready?"

"Uhuh." I see tears in his eyes. Settling my body down next to him, we hold each other close. I want to help Buck get over his fears, not break him.

"I think they know." He's wiping his eyes. I give him a puzzled look. "My folks. I think they know I'm gay." There it is.

"Is that what you are?" After a quick kiss, I give him a big broad smile.

"Yeah. I'm a gay guy, Tom. Just like you."

"So..."

"So I'll drop the girlie thing. You're not a girl. You're every bit a man - my man. I really never wanted to be with Bunny, or with you as a fake chick...but admitting to myself that I am gay is not easy to do, Tom." Another quick kiss, and we need to talk more.

"Oh, Buck. I know how hard this is for you. Look, your folks know you better than you do!" That brought a smile back to his cute face. "Mine knew way before I came out to them. It's just the way it is."

"I guess." One more kiss won't hurt.

"We can stop for now." I've been gently stroking his muscular chest as we talk.

"Let's do it! I've beat off lots of times with you in my head, Tom...in my mouth...up my ass. Let's make it real."

Part 2 -

"I have something to give you first."

"What is it?" I'm getting off the bed and going to my dresser. As I open the drawer I keep it in, I wonder for a second if it's the right time. It is.

"This is something I had made for myself the first week of high school, right after I saw you at practice. I wear it, a lot, to feel like you're with me. This kind of role playing will be good for the both of us. Put it on, please." With a shake of my hands to unfold it before his eyes, Buck is now all smiles.

"No way! My football jersey...number and all!"

"I made it into a crop top. It was sexier that way."

"You're sexier this way!" Ooookay! Damn he's a strong one. Practically lifted me off the floor and on top of him. "I love it! Thank you, Tom."

"Put it on." Oh, the joys of watching my guy lift his arms...and seeing those hot hairy pits!

"It fits good. You wore this? Where? When?" The look I'm giving Buck says it all.

"No way. It's your jerk-off jersey?" Just a casual nod from me will do.

"Every time I put it on, you were there...in my mind, at least, with me. It cast an instant spell on my mood, getting me all into fantasies of being with you...making me horny and hard as hell in an instant."

"You're the best, Tommy."

"Like I said, Buck, some role play can be fun, for the both of us. Let's leave it on while I fuck you. Headline: 'Nerd fucks player stud right on the field after practice.' What do you think?"

"It's a lot better than what I put you through. I'm really sorry, Tom."

"Don't tell me, show me! Make it up to me, Buck. Lift those hunky legs of yours so I can line myself up with your goal post! Take it from me, lover...bottoming is the bomb. Applying the lube. He sees the target. He lines up for the goal. Not a defender in sight! He reaches the ten, the five,.....He's in! Tommy Masters has just sunk himself into his goal! TOMMY MASTERS SCORES!!!!!"

"Fuck you're big!" His face looks like he isn't sure whether to be in pain or in pleasure.

"Not really. It just that way at first. I'll hold still until you tell me that you've adjusted to having my monster sized man-meat up inside your guts."

"Dufus."

"Buck?"

"Yeah?"

"This feels like destiny."

"What do you mean?"

"When you were inside of me yesterday, how did you feel?"

"Great! Like it was exactly where I was meant to be. It was like my cock knew it had found its home; and I knew I had found the one right person to be with. With you, Tom."

"Exactly. That's what I mean by destiny. I bet when you came inside of me you knew what I'm getting at, right?" Before he can answer, I'm bending down for a kiss. As I start to straighten up, Buck grabs me by the shoulders and holds me steady. His eyes are plunging into mine.

"It was all I could think of, all I could hope for, all I ever expected, but more. It felt like my whole body was only good for one thing, to transfer all of me into all of you. Weird, huh?"

"Beautiful, Buck. Not weird at all. You ready for me to fuck us both into nutting?" He nods.

Part 3 -

Buck is releasing his hold on me; and I can straighten up now. As this is my first time inside of him, of any man, I want to take it slow. I want to be totally in this moment; and noticing each and every tiny activation of each and every nerve cell in my body - especially the ones at my crotch!

"Why are your eyes closed? I thought you liked watching me."

"I do, that's for sure. But they are staying closed, so I can just feel how your body and mine are melting together. Right now, before I move inside of you, it feels like I've been given a permanent sheath to keep my permanent erection nice and warm. Man, this feels good!"

"You feel good to me, too, but a little thrusting might make it even better...?" One very deep breath taken in...and very slowly exhaled. The scent of us together...of our bodies...of the perfume Buck gave me...of the heavy musk of our sex together...it's all making my head swim in the most wonderful way possible. Eyes opening now. My belly and the back of Buck's thighs are in view. As I look a bit lower, what I can see of my pubes makes me shudder with excitement. The total reality that my cock is inside of him just hit me!"

"You mean like this?" I couldn't even see the root of my dick, it was so deep up his hole. Now that I am very slowly pulling it out - just a few inches - it glistens with the same wetness that I loved seeing when Buck was fucking me. His ass crack is a hairy one, and I love it. As I start to push in again, my eyes close once more to the incredible sensation of my skin rubbing against his. It feels like my body is on autopilot now. I just want to cum inside of him. My thrusting is timed to the clock - in one thousand, out one thousand in...exactly a second for each movement. The rhythm has me hypnotized.

"Fuck this feels good. Guess we're both verse, huh Tommy?" My eyes are staying closed. I nod my agreement. There's probably a lot of technique we both need to learn about fucking, but for now, I'm good. Real good!

"Mmmm." Without opening my eyes, I reach down and my hand finds Buck's cock - rigid, warm, and wonderfully wet with his precum.

"Fuck, yeah. Oh, fuck. Pounding my ass and fisting my...it feels...it..."

"I'm close, too. Hold on for me. Let's blow together!" Twice as fast now, that's my new pump speed. Man, my nuts are slapping on his cheeks, and the sound is hot! It feels to me like all of my inner plumbing has just opened up somehow. Is that my milk I feel gurgling inside of me? My fist is keeping time with my thrusts; and with eyes now open, I see that Buck is just as close as I am.

"Sure. Maybe. If I can...if I... TOM!" He yelled my name and it burst through my body like a tidal wave. I want to hold him close. I need to feel his... "ANGHHH!!" He's nutting and the muscles inside his ass are gripping down on me! Ooohhhh. So good. So tight and warm....What's this? This feeling is new. I never... everything is going into slow motion. My balls are throbbing. My taint is throbbing. The muscles inside my crotch are pumping a super load through my cock...and it all feels surreal. Nothing is gripping my mind like it should - like it always has done before, whenever I cum. This just feels like I'm on some kind of wonderful drug that is automatically milking me. I feel happy, yet inexplicably calm. Amazing!

"Oh, man. That was intense! I made a fucking mess - look at my chest!" He's wet with his own cream. I'm just about emptied out myself.

"Nice...looks nice. Need a second here... AHHhh! Good. That was my last rope."

"You look like an angel." Buck has his hands on my flanks.

"I was somewhere strange - with you, for sure, and also not quite with myself. I can't explain it." He looks like he knows.

"You don't have to, Tom. I felt the same way yesterday being with you. I think it's something that is beyond just raw sex and physical needs." This is a new side to Buck.

"You hit it just right. That's what it is. It think there's a real good word for it."

"What is it?" He may think it's way too early to hear it, but here goes:

"Love."

to be continued...

Corjix
Corjix
182 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
1 Comments
CorjixCorjixover 1 year agoAuthor

I think there will be one more (closing) chapter for Tom and Buck. They have helped me to experience what might have been in my own life...and I want them to finish their journey.

Share this Story

Similar Stories

Wrong Number? Maybe Not! Ch. 01 A misdial leads to the best sex of his young life.in Gay Male
The Slutty Femboy Next Door Older man fucks a bratty naughty femboy.in Gay Male
My Secret Initiation A gay initiation fantasy based on real experience.in Gay Male
My Wife's Fucked up Family Pt. 01: Lily's Clit Wife's family has no limits, her sister has a giant clit.in Gay Male
Two Old Men Make Me Their Bitch A trip to Palm Springs sends me down a point of no return.in Gay Male
More Stories