Boobs-R-Us - Pt. 02

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A guy, a some boobs, some unexpected life changes.
18.8k words
4.78
6.3k
16

Part 2 of the 2 part series

Updated 05/24/2024
Created 05/20/2024
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A big thank you to Kenjisato who was kind and motivated enough to edit another of my stories. I appreciate them and all of their talents and time! People like them are what makes the lit community great. Thank you, Kenji.

This is the second part of the story and jumps right in. I'd suggest you read the first part, well, first. I wrote this as one continuous story but realized that it was a bit too long for a single story on this platform, so I split it down the middle. Please forgive me if this frustrates you.

All characters in this story that engage in any kind of sexual activity are consenting and over the age of 18. If you don't enjoy stories where the characters end up with body parts that generally belong to the opposite sex and then enjoy using them, this probably isn't for you. All characters are fictional, we just wish this could actually happen.

Boobs-R-Us Part 2

---

The next morning, I awoke to golden light filtering in through the curtains. An arm stretched across my body and a hand gently cupped my boob. Behind me, I could feel breasts pressing into my back and a pair of warm thighs pressing into my ass as Rebecca spooned me.

It was the most wonderful way I could ever remember waking up. I sighed in contentment. The previous night, I learned that I was two people. One was James, the man, the other was Jessica, the woman with a bit extra. I felt whole knowing that both possibilities existed inside me.

I felt much better than I had the previous morning. I was glad that I'd only had two and a half glasses of wine. I wanted to lie here and enjoy the moment, to enjoy the warmth of Rebecca's body snuggled up to mine.

I could see the silhouette of a pair of panties tossed into the comfortable-looking accent chair in the corner. I was pretty sure they were mine. Nearby, my outfit hung from the curtain rod. Rebecca had oh so carefully hung each garment on a hanger before teaching me what it was like to have sex as a woman with a woman.

My mind drifted, I could almost feel her hands and mouth as they roamed my body. This time, it didn't feel like it happened to someone else; Jessica may have been in the driver's seat, but as it turns out, I am Jessica.

-

Rebecca's room was the picture of warm comfort. A large four-poster bed with a fluffy-looking comforter was the centerpiece of the room. A comfortable armchair sat in the corner next to a stack of books. Her closet door was slightly ajar, revealing shoes neatly hung from the back. She pulled me in for another kiss before spinning me around to gently remove my unbuttoned blouse, which she promptly hung up. Her hands seemed to fly as she unbuttoned my slacks, and slid them down over my hips and legs.

I honestly had no idea that someone removing my clothing could feel so sexy. Her fingers glided along my skin as she removed each piece. Her touch felt electric and new, somehow different than any other sexual partner I'd ever had.

She paused and had me sit on the armchair, while she removed my heels. Again, I found the way she did it an incredible turn-on. A constant low buzz ran through my nervous system. As she removed my heels, I got a good look down her shirt, my mouth watered as her breasts came into view. I couldn't wait to see them.

When she stood, I realized how much taller than me she was. She took my hand and helped me out of the armchair. I stood for a moment, taking in the fact that she stood at least five inches taller than me, even without shoes. She leaned down and lifted my chin to give me another kiss. Her hands started unbuttoning her blouse. I tried to help, but she moved my hands so that my arms rested around her neck. I missed my first view of her breasts encased in their bra, as she kept my lips pressed against hers.

She unbuttoned her jeans and pulled away from our kiss so she could push them down her generous hips. I moved to help, and she let me, so she could rid herself of her shirt. I got a glimpse of her breasts as I pushed her pants down. They were full and round, not huge, but more than a handful for me. I didn't stop to stare, I noted the maroon bra and moved on. Her pants were down far enough that I could see the tops of some silk panties that looked like they might match her bra.

Her jeans were tight and took a bit of tugging, but once they made it past mid-thigh, they gently slid to the floor to join the blouse already there. I moved to pick them up like she had done for my clothing, but she grabbed my hand and pulled me toward the bed. I followed and ended up wrapped in her arms. She was warm. Her breasts were just below my chin, she lifted my chin up again and kissed me. I got lost again in her soft lips. She was probably the best kisser that I had ever experienced.

When she pulled away again, it was to remove my bra. Somehow, without me knowing, she had undone it, and her magic fingers had moved it so when she tugged between the cups, it fell to the floor. I felt out of breath and excited all at the same time. The buzzing in my nervous system had increased, as though the current had been turned up.

Rebecca gently caressed my breasts and softly asked, "Are you ready to feel like the woman you are?"

"Yesss..." I didn't mean to moan, but the incredibly girlish and wanton sound came from my mouth anyway. I sounded like someone in heat.

She smiled and pulled me gently to the bed.

Once I was comfortable, she undid her bra, freeing her breasts in a simple, practiced motion. They were as perfect as I had hoped. Perky, pale, with dark pink nipples that verged on light brown. They were already hard, thick, and seemed to prove her womanhood more than any other feature about her I'd seen.

She straddled my hips and grinned at me. "I'm going to make you scream without ever touching your clit..."

Scream I did. I can't describe all of the things she did to me. All I knew was that her hands and mouth seemed to know every spot to gradually bring the buzz in my nerves to a crescendo. Much of what she did was to my boobs and nipples, but also my hips, my neck and around my ears. When I finally reached the limit, something inside of me exploded, like it had never happened before. I had heard that dry orgasms were possible, but never could have imagined the waves of pleasure that consumed me. She never once touched the parts hidden in my panties. She traced around those parts and gently pressed on my rosebud, but never under the fabric.

I screamed her name and then panted and screamed again, as another wave spread out from somewhere between my hips. There was no doubt that I was having an orgasm. How she had done it was a mystery.

She lay next to me and gently caressed my skin, while I recovered. Once my breathing was back to normal and I was able to open my eyes, she spoke softly, "So how are you with your tongue? Getting you there... got me all worked up..."

-

My tongue is magic. Yes, I'm bragging. But ask any of my exes since Ashley. I spent so much time dressed as a girl, between her legs, that I knew her bits better than I knew the back of my hand. I really enjoy it. It's so intimate. The buildup, feeling her squirm as she gets to the edge, and pulling back, at the last moment, to keep her there until she is a hot mess.

Then the climax. The truth is, I came once just getting a girl off with my tongue. It was a little embarrassing, but her reaction was so hot that I blew my load just as she clamped her legs around my head. I covered by getting her off again. She didn't complain at all.

I've probably spent four times as much time between my exes' legs since Ashley, as I have inside them. When you give head as good as I do, they start to expect it every time. I can't say I've ever minded.

-

"Let me show you," I purred, and shimmied down her torso.

She had lost her panties at some point. When exactly, I couldn't recall. She had trimmed nicely, but still had quite a bit of hair in a lovely V, pointing right where I wanted to go. She smelled heavenly. A hit of vanilla and honey overlaying her more womanly musk.

I spread her legs gently and spent a little time getting to know her bits.

-

No woman actually has a porn-star pussy. Every pussy is different, and each is a joy to learn. Most guys dive in and go right for the sensitive bits. I'm sure that works for some women, but I like to take my time. The tease starts with getting to know what makes each woman tick. A tickle here, a lick there. Pay attention, and she will be moaning before you know it.

-

Rebecca was within a few minutes. I hadn't even touched her clit, and she was already shoving her lips into my face.

-

I couldn't be certain then, but I know now that when I'm Jessica, I enjoy eating pussy even more than when I'm James. I think it was Rebecca's that somehow solidified that forever in my psyche.

-

After I'd gotten to know her intimate bits and enjoyed teasing her for a while, it was finally time to make Rebecca climax. Her thighs were a quivering mess and I could tell that she needed it badly. A quick tongue into her honey hole and I, at last, moved to her clit which was still nicely hidden. A few circles and then a consistent, slow flick across her lips caused it to appear.

I blew on it, and her legs drew up off the bed. Two slow licks around it and then a light flick across it, was all it took to elicit a scream from her as her legs shook. I kept up my work around her clit to keep her rolling before moving back to the other pleasure spots I had found. She recovered for a moment before I moved back, positive I could bring her back to the brink once again.

This time, I kept her clit covered, swiping back and forth, but never applying direct contact. She quivered and panted above me. My nipples dragging on the sheets were a delight that urged me onwards. I picked up the pace of my tongue swipes and slid a single finger inside her to seek that spongy bit known as the G-spot. I wasn't sure she had one, not every woman does, but I got lucky. Just past my second knuckle I brushed a spot that caused her to pull her thighs closed and utter a hot, "FUCK!" from above me. I started slow circles around that spot with moderate pressure, while I alternated patterns with my tongue.

She exploded.

Her legs clamped down on my head and juice splashed out onto my face. Each time my tongue slowly pulled across her clit, her abs contracted, causing my nose to dive into her pubic hair. I slowly removed my finger and relaxed my tongue. She panted out, as aftershocks ran through her, causing her legs to spasm gently. After her thighs slowly fell apart, I climbed back up her torso to let our boobs mesh and give her a Rebecca flavored kiss.

When I let her lips pull from mine, she breathed deeply. "Jess, holy shit. You're better than almost any woman I've ever slept with. Unngghh. That was fantastic!"

"I'm glad you liked it. I have had a lot of practice." I smiled at her. It was true, and a girl likes to be told she's good in bed. Doesn't matter who her partner is.

We lay there for a long moment. I caressed her breasts as I watched them rise and fall. Eventually, Rebecca's breathing slowed and her hand found the bulge in my panties that we had been ignoring.

"Jess? I think I want to see your clit."

"Really?"

"Yeah. I'm not a fan of dicks, but since we're all girls here, I think I'd like to see it."

"Okay..."

I let her pull down the two sets of panties until my clit pulled free from between my thighs. The head was slick with my juices, I knew there was a big wet spot in my panties. She moved, so she could see it. Her thumb ran across the head for a moment while she gripped the shaft.

"I think you should put it in me." Her face looked thoughtful. "This is a one-time thing, but I think I'd like to know how it feels..."

"You sure?"

"Yes. I'm not usually into trans girls, but with you? It feels right. Just... don't cum in me. Pull out or something."

"Okay. Do you want to be on top?"

She thought about that for a moment. I really wanted her to be. I felt like that was the only way I should be allowed to be inside her. She still needed to be in control.

"Yes. I do."

We shuffled on the bed until she was hovering over me. The view was pretty erotic. My boobs partially blocked my view, but I could see the head of my clit pointing up, waiting to fulfill Rebecca's request.

I didn't even hesitate to call it a clit. Rebecca had called it that and it had seemed right. James had called it many things over the years, but never a clit. But, I wasn't James right now-- I was Jessica, and she has a clit.

Rebecca shifted her hips up and with her fingertips, pushed my clit into her warm tunnel. Somehow, it felt like the first time all over again. In a way it was. Jessica had never done this before, only James. Jessica had lost her other v-cards while pretending to be Jackie. Rebecca, here, was taking her last.

"Hmmm, this feels nice..." Rebecca began grinding her hips while lifting gently. I let her guide me and met her thrusts with my own, being careful to let her control the depth and pace.

She leaned down and kissed me while continuing to rock her hips, pressing her clit into me, as my clit moved in and out of her. The way our boobs touched felt so much more electric than when I had been in this position as James.

She sat up again and reached down to stroke her clit as she increased her tempo. I watched her capture a bouncing breast and pinch and roll her nipple. Her eyes closed and she moaned.

I was tempted to follow suit and play with my own boobs, but I was worried that any extra stimulation would send me past the point of no return. I was having a hard enough time keeping it under control as it was. I had promised, and as Jessica, I didn't want to blow it by having a short fuse my first time with a girl.

Rebecca was really getting into it. Her moans increased in volume and her thrusting increased in tempo. I couldn't help but feel like she was getting off more on her own fingers than she was on my clit. The little voice that was James wanted my clit to be the focus; Jessica just let Rebecca find her own rhythm and pleasure.

When her vagina clamped down on me and she stopped thrusting, I knew she had reached her peak. I closed my eyes and tried to imagine the look on her face as she finished with two hard thrusts and her moan escalated until she panted heavily. I was close, but I was sure I could hold off if I didn't focus on how erotic it was for Rebecca to be riding me right now.

The night before had been lust and alcohol-fueled sex. It had been a prelude to Jessica's coming out. This night felt like it was Jessica's coming out party. Slow, hot, and romantic.

Rebecca finally slowed and placed her hands on my boobs. I could feel her heavy breathing through her hands and her hips. I opened my eyes to see her smiling down at me.

"That was pretty fun! Definitely a better connection than with a dildo. I'm glad my first time was with you. You didn't come yet, did you?"

I shook my head. "No, I'm close, though, maybe I should pull out..."

"Oh? That close?"

"Yes." She moved a little and I gasped. "Don't move too much. I'm so close."

"Oh."

"Go slow..."

She lifted her hips slowly. Every inch got me closer to exploding. Once I slid out, my clit flopped down in a wet plop, and she settled her weight on top of it. I gasped, as I felt her lips slide along its length.

She grinned when she saw my expression. She started sliding her lips along the length, leaving the tip exposed on my belly. My hands grasped my boobs as I rapidly came closer to the point of no return. The moment my fingers touched my nipples, I felt the current jump to my clit and I exploded.

Jets of cum spurted from between her slick lips and onto my stomach and breasts. I couldn't help but moan. The girlish sounds that escaped my lips made me smile. It was the perfect end to the moment. I actually felt like I had climaxed like a woman.

Rebecca rolled off me, smiling again. I could get lost in that smile. "Jess. Thanks for doing that for me. I also appreciate you letting me be on top. It felt more... I don't know, like girl sex."

All I could think to do was smile back. I really felt like I was a teenager having sex for the first time.

We lay there for a moment before Rebecca spoke up. "Hey, do you like to be... umm, how do I put this? Be penetrated?"

I thought about Jackie's enthusiasm for taking Alex. I hadn't even had a finger up there before and I'd loved having Alex give me everything he had.

I nodded. "Yes. I do. I just found out actually..." I turned a little red as I admitted it. James was embarrassed; Jessica knew she loved it.

Rebecca's smile returned. "I think I have a treat for you."

She jumped up and walked into the closet. When she walked out, she was wearing a harness with a long, flesh-colored dildo sticking out from between her legs.

"Meet Jane. She tickles all the right places. You ready to ride?" She grinned at me in a vivacious way.

If I hadn't just cum, I would have been instantly hard. For the first time in my life, I wished I had a real pussy. The flesh-colored tube was definitely larger than what I had on my best day, but smaller than what Alex had filled me with. I wanted it. I needed it.

She saw the need in my eyes and strutted to her nightstand, where she pulled out a bottle of lube. "Okay, you little minx, how do you want it?"

I'd only done it missionary and doggy style with Alex. I considered it. On top sounded really fun, and she had just enjoyed the same position. Somehow, it felt right. This was my choice. This time I would control the pace and the depth, just, from the receiving end.

"Cowgirl, and I want you to play with my boobs."

A moment later, we were in the same positions we had been earlier, except it was Rebecca looking between her breasts at a phallus standing straight up, and I was the one to shift my hips up to mount the hard shaft. I think I surprised her with how readily I popped up, used a finger tip to aim, and speared myself. My clit jumped as she filled me and I let out a moan. Why had James denied himself this pleasure all these years?

I rocked my hips like Rebecca had. Her hands rose to meet my boobs as they started to bounce. This was heaven. A beautiful woman playing my boobs expertly, her thighs meeting my cheeks as she filled me. Jessica banished James for the moment, and I became the wanton sex goddess I had been the night before. My moans rose in volume. I didn't care if the neighbors heard. I was a woman reveling in her pleasure. Rebecca seemed to read my every move and met me, stroke for stroke.

Her hands and fingers played my body like they had before, my nipples telegraphing her intentions to my hips. All too soon, I felt the warm tingle build and expand. I closed my eyes and sang out. My clit drooled puddles on her abdomen and I clenched down with a few hard thrusts as my body shook.

With Alex, I had screamed out. This time, I moaned Rebecca's name as an orgasm that mixed what I'd experienced the night before and what she had given me earlier. It was focused deep inside me, it spread in growing waves. Each starting with a spurt from my clit and ended with a tingling in my toes and fingers, spurring me on to try to get her deeper, to scratch an itch I never knew I had. I wanted more, I needed more.

I'm not sure when or how it happened, but at some point, I passed out. When I woke up, still delightfully filled, she was drawing patterns on my back as she gently thrust her hips upwards. A gentle rumbling was traveling through the shaft into my ass and Rebecca was softy grunting.

I learned why a moment later, when she stopped suddenly, and her legs shook. Part of the dildo was inside her and she achieved her own bliss right after I had woken up. All I knew then was-- I felt like a complete woman. Being on the receiving end of release, and my partner taking theirs from penetrating me, somehow checked my box.