Study Group Surprise Pt. 02

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James embraces being a femboy.
5k words
4.78
47.9k
110

Part 2 of the 2 part series

Updated 06/10/2023
Created 09/14/2021
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James19999
James19999
342 Followers

This is the second part of a story I published in September. You can click my profile to find the first part. Because it was so long ago, I worked a recap into the first part of this installment. I didn't intend for this to be a series, but the first one got a good reception and I was struck with inspiration lately, so I decided to write a sequel. I might publish more installments, or I might not.

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I was sitting across the table from Mandy and Tana. It was funny how just three days after the first study session, so much and so little had changed. Just like last time, my heart was racing head was swimming with sexual fantasies, making it hard to focus on the organic chemistry we were supposed to be studying.

But last time, my urges had been directed at Mandy, the classically beautiful blonde cheerleader. Now, I couldn't stop thinking about what had happened last time after I was left alone with her roommate Tana, the things she had done and made me do. Maybe it was wishful thinking, but it seemed like she was too, the way she kept flashing my knowing little smiles when Mandy wasn't looking and the way her foot kept brushing against mine under the table.

"Going to the bathroom. I'll be right back." said Tana, standing up from the table and crossing behind me to her bedroom. I stared at her longer than I should have, admiring the way her high-waisted shorts and floral patterned crop top showed off her bulging thighs and powerful shoulders.

Realizing I should probably stop staring, I turned back around and faced Mandy, who was now leaning across the table and looking at me with a twinkle in her eye and a sly grin.

"I think Tana likes you." whispered Mandy as soon as Tana was out of the room.

I opened my mouth but froze, not sure what to say. There's really no good way to tell a girl that her roommate made you wear one of her bikinis and pegged you. So all I managed to say was "Really?"

"Yeah!" she replied quietly but excitedly. "I'll tell you what. When we're done studying, I'll go out for a run and leave the two of you alone so you can ask her out."

My heart started racing as I thought of being alone with the aggressive, dominant Samoan girl again. My butt was still a little sore from the last time, and I felt a strange mix of fear, guilt, and arousal wash over me. I realized Mandy was still looking at me, expecting a response.

"Thanks," I managed. Mandy giggled, clearly enjoying playing the matchmaker. A couple minutes of awkward silence passed until I heard Tana's door open and she returned to the table.

The last fifteen minutes of the study session dragged on even more than the first half-hour did. My heart raced with nervous excitement, knowing that I was about to be alone with Tana again, wondering what she would do this time. I remembered how it felt to be pinned underneath her weight as she thrust into me over and over and over, my dick growing hard with anticipation even as I felt a twinge of fear.

Finally, Mandy released me from my torment. "I think that's enough for today." She said, standing up from the table. "I think I'm going to go for a run." She flashed me a grin and winked as she turned and walked to the apartment's door.

Unlike last time, my eyes didn't linger on her too long as she left. It was funny; Mandy was the kind of girl who some guys would kill for a night with. Shapely legs, thigh gap, pretty face, blonde hair, blue eyes, thin waist, flat stomach, round butt, c cup breasts large but not huge. But I couldn't imagine those slender arms pinning me down or her hourglass frame on top of me or those hips driving a strapon into me. I couldn't imagine that golden hair falling all over my head and shoulders, couldn't imagine those pink lips pressed to my earlobe, whispering demands that I admit I liked being pegged.

Tana stood up from the table and stretched. The motion showed me the outline of her abs, the striations of the muscles of her shoulders, and powerful mass of muscle in her thighs. Her eyes followed Mandy until the cheerleader shut the door behind her, then turned to me, a mischievous smile forming on her face.

I stood up from the table, words catching in my throat. Tana must have been almost six feet tall, standing several inches taller than me. I couldn't meet her gaze and turned away nervously, my heart pounding in my ears. I noticed her making her way around the table toward me. Some instinct in me made me back away like a gazelle trying to get away from a lion.

"Wait!" I said. "Can we talk?"

Tana stopped and looked at me, a slightly puzzled expression appearing on her face. After a moment that felt like it dragged on forever, she shrugged and sat down on the couch.

"About what?" She asked, patting the spot next to her on the couch. Starting to tremble, I walked over to the couch and sat down a foot away from her. She scooted closer but stopped just short of brushing up against me. Sitting right next to her highlighted just how much bigger she was than me, her thighs nearly twice as thick as mine.

"About..." I started, not sure I could say it out loud. I could feel her eyes burning into me as I looked down at my feet. "About last time."

"What about it? I thought you liked it."

My cheeks burned as I tried to sort through my tangled jumble of feelings. Humiliation at the way I had been overpowered by a girl, forced to dress in a bikini, and fucked in the ass. And shame at how Tana had shattered my masculinity by making me like it. I had even called her daddy. But I had liked it. Even with the way my butt was still sore, I could remember being rocked by that full-body orgasm, and how gorgeous I looked in the bikini.

"I did, it was just really... intense." I finally replied.

She gave me a sheepish grin, and if her skin weren't brown, she might have flushed red.

"Sorry. There's just something about you that drives me wild." said Tana.

Now it was my turn to blush. Growing up, I had always been weak and scrawny, bullied by guys in school and ignored by girls. Now that I was in college, I didn't get bullied anymore, but my luck with girls hadn't improved at all. At least until three days ago, if you could call that luck.

"Ah, so Mandy was right. You do like me." I said playfully, turning to humor to try to salvage some of my dignity.

Tana laughed. "I guess I'm not so hard to read."

"Yeah, you were so subtle last time."

Tana laughed again, then reached down and took my hand, face turning serious.

"Listen, James..." she said, looking down at me. I turned to look at her and saw her brown eyes staring into my eyes. "I really, really want you."

I stared back, not sure what to say. No one had ever told me anything like that before. And deflecting with another joke felt wrong. We stared at each other for a moment, and then Tana broke the silence.

"It's just... you have a really pretty face. And the way you're so shy and get flustered so easily is adorable." Tana paused for a moment, then cracked a wicked smile. "Not to mention that ass." True to form, I could feel my cheeks flush with heat. She placed her other hand on my cheek, holding my head still and forcing me to maintain eye contact. "I really want you to be mine."

I stared back for a long moment, my hands and face in her hand. I couldn't help but admire the way her bicep bulged as she bent her arm, and the thickness of her shoulders. My heart raced, but there was something comforting about being held by someone so strong. But despite her strength, I could feel her trembling with nervousness.

"Okay." I finally said, softly. "You can have me." I turned my head slightly in her hand, kissing her fingers gently. Her face lit up and she grabbed me by the waist, pulling me onto her lap. I let out a slight yelp of surprise as I found myself sitting on her bulging thighs, feeling the powerful muscle just underneath me. She leaned in, hungrily kissing my neck, her hand sliding off my cheek to tug at my shirt. I lifted my arms to try to help her get it off me, not nearly fast enough. She grabbed the collar and tugged, striations visible in the muscle of her forearm, and I heard my shirt rip.

"Oops." She said, pulling her lips off my neck. "Looks like you're going to need a change of clothes."

Her other hand reached down and unbuttoned my jeans. I stared at her, breathing fast, not sure what to say.

"I left a little present for you on my bed. How about you go change into it?" she asked playfully.

"You were planning that, weren't you?"

She shrugged, but the smirk didn't vanish from her face. "Well, get to it."

I gave an exaggerated sigh, matching her playful energy, and stood up off her lap. My jeans, unbuttoned and unzipped, fell to my ankles.

"You can leave those here." She said. I stepped out of the jeans and turned toward the door to Tana's bedroom. Before I could take a step, I felt her hand grabbing my boxers. "Those too. And the socks." I felt nervous about stripping in the middle of the living room, but we were alone and I didn't want to argue, so I took off my socks and underwear, leaving them with my jeans and my shirt on the floor. Tana wolf whistled as I walked away, but she couldn't see me blush with my back turned.

I stepped into her room and looked over at the bed, the same one she had fucked me on just days before. There was a shopping bag on top of the covers, and my heart skipped as I wondered what was inside. I could feel an intoxicating mixture of shame and excitement as I realized I would be dressing up as a girl again for Tana. Reaching into the bag, I pulled out a small dress and a pair of lace panties.

I started with the pair of black lace panties, stepping in and tugging them on. With my erection tugging the material to the front, they barely covered half my ass cheeks, leaving the pale, round outer part of my butt exposed. Next, I unfolded the dress and held it out in front of me. It was a white sundress with spaghetti straps and no button or zipper. Never having worn a dress before, it took me a minute to realize I was supposed to pull it on over my head.

I slipped into the dress, guided the straps onto my shoulders, and straightened out my hair, then looked into the mirror. My heart skipped a beat as I looked myself up and down, and I couldn't help but grin. I looked good. Damn good. I was a scrawny guy; I could never really fill a shirt, and my clothes always looked baggy and shapeless on me. But here, my slender frame was an asset. I couldn't help but admire the way the straps sat on my narrow, delicate shoulders, or the way the midsection of the dress hugged my thin waist. And I certainly couldn't complain about the skirt of the dress falling to my mid-thigh, showing off slender but round legs that just seemed to look right in a skirt. Smiling with a confidence in my appearance I wasn't used to having, I walked back out the door into the living room, eager for Tana's reaction.

"Oh hell yes!" said Tana, still sitting on the couch. I grinned as I saw her face light up, incredibly pleased that she liked how I looked. "Do a twirl for me." She said.

I obeyed, spinning in place and letting the skirt of the dress fly up, exposing my upper thighs and the panties. But my excitement at feeling the dress fly up turned into stone cold dread when I saw the window with the blinds up behind me.

"Oh, shit." I said, realizing that anyone outside the window could see me like this. I hurriedly rushed toward the window and grabbed the cord of the blinds. But before I could pull, I felt Tana grab my wrist. She pressed her body against me from behind, left arm wrapped around my waist, pulling me up against her. I felt helpless in her arms.

"What are you doing?" She asked, leaning in so that her lips brush against my ear.

"Closing the blinds. I can't let anyone see me like this!"

"Relax," she purred. "We're six floors up. No one can see your face from down there. All they'll know is that I'm scoring a hot piece of ass."

I turned to face her, my back pressed against the glass of the window. She leaned in even closer and cracked a smile.

"If you're that worried about privacy, the blinds are all closed in my room." said Tana suggestively. I looked up at her for a moment, unsure of what to say.

"Come on." She said, pulling me away from the window. I felt her give a quick slap on my ass and started toward the bedroom with a jump. I darted inside, still scared of being seen through the window. Tana followed me in and closed the door behind her. She licked her lips and my heart raced as I thought about what she had done with me last time we were alone in her room.

"Looks like I've got you all to myself." she said, padding over to me. I watched her, my mouth hanging open slightly, waiting to see what she would do. I trembled as she ran a finger over my shoulder, then stepped behind me. Frozen in place, I watched us in the mirror across the room.

Just like last time, I was struck by the sheer contrast between our appearances. She was tall and powerfully built, her high-waisted shorts and crop top leaving little to the imagination. The layer of fat over her muscles was thick enough that I couldn't see the exact outlines of her musculature, but thin enough that it didn't leave any doubt that most of her weight was lean mass, not flab. Her thighs were like tree trunks, and her arms were almost as thick as my thighs. I stood in front of her, small and pale in comparison. She was showing much more of her skin than I was, but she radiated a confidence and a strength that made it obvious who was the dominant one here. This was not a relationship of equals.

She stood behind me, running her hands down my thin arms and leaning down to kiss my ear. Her left arm wrapped around my waist again, pulling me up against her solid, hard body as she showered kisses on my cheek and ear from behind. I moaned softly and leaned back into her, feeling safe and totally caught up in her embrace. She ran her right hand down my side and gently grabbed a handful of my ass before sliding it down my thigh.

She leaned back and sat down on the bed, pulling me with her onto her lap. I sat on her lap happily, feeling her powerful thighs underneath my soft legs. I closed my eyes and sank into her, her arm still wrapped around my waist, my body touching nothing but hers. We sat like that for a minute, her lips still kissing my cheek and my scalp gently.

"God, I love how soft you are." she finally said. I opened my eyes as I felt her turning us around, laying me flat on my back on the bed. She parted my legs and slid between them, wrapping my thighs around her hips as she leaned down to kiss me on the lips. I kissed back eagerly and closed my eyes, Tana's weight pressing down on me, pinning me to the bed and yet making me feel safe at the same time.

I opened my eyes to find her smiling mischievously at me again. I almost asked why before I noticed that my erection was poking at her from under my dress. I looked up at her sheepishly and blushed. She giggled.

"When I pegged you last time, was that the first time anyone ever, uh..." her voice trailed off, thinking about the right way to ask the question. "The first time anyone fucked you in the ass?"

"Yeah" I replied, a little shocked at her bluntness.

"Really?"

"Is it that surprising?"

"I mean, yeah. You're kind of built to be fucked."

"What?"

Tana rolled off of me and lay next to me. I looked over at her, waiting for her to explain. She gave me a nudge. "Roll over."

I obeyed, rolling over onto my stomach but still looking over at her. She reached over and lifted the skirt of the dress up, exposing my ass, only half-covered by the lace panties. Tana playfully slapped it, watching it jiggle under her hand and I jumped a little in shock.

"Come on, you can't deny you have a really nice ass. That plus the soft skin, the cute face." I blushed bright red.

"I guess I do have a nice ass." I conceded.

"And so submissive too." she continued. "Not like you try too hard to keep anyone out of it."

"What?" I asked, bolting upright.

"The first time we were alone in a room together, I had you wearing a bikini and taking it up the butt within fifteen minutes."

I opened my mouth to argue, but realized I didn't have a comeback. I really had let her peg me without much of an argument. Seeing me flustered, she smiled again.

"What about you?" I asked. "Have you pegged a lot of guys? Who just keeps a strapon lying around?"

Tana giggled. "Want to hear something funny?"

"What?"

"Come closer."

I rolled toward her, my side brushing up against hers.

"Closer."

I sighed and crawled on top of her, my head near hers. She leaned in and brushed my ear with her mouth.

"You're the only one." she whispered. "I bought the strapon just for you."

"Wait, what?" I asked, bolting up and looking down at her. She didn't even bother to hide her glee, giggling as I stared at her.

"Like I said. There's something about you that drives me wild. And I figured you'd probably put out without too much of a fuss. And I was right."

I didn't even realize it was possible for me to turn so red. She laughed again and reached up to stroke my cheek. I looked away, humiliation washing over me. Tana sat up, rubbing up against me.

"Hey, it's okay. I like that you're submissive. It's nothing to be ashamed of." She said. I let her pull me in close, kissing me on the lips again. She wrapped me in her strong arms and I eagerly returned the kiss, running my hands over her powerful delts and lats, feeling the muscles playing underneath the skin.

"I could use a massage." She said, looking down at my hands on her shoulders. Tana lifted her arms and I silently pulled the crop top off over her head, revealing b cup breasts sitting on a sturdy chest. She turned and lay face down on the bed.

I straddled her waist from behind and dutifully began kneading the muscles of her upper back. It was the leanest part of her body, and I could see and feel her rippling muscles under my hands. Finding a knot, I pressed down on it. She let out a moan of satisfaction as I released the tension. I leaned down, feeling small and delicate on top of her powerful body, and kissed the back of her shoulder. Tana turned her head and smiled.

I continued the massage for a few more minutes before Tana grabbed my hand. "I needed that." she said contentedly. She rolled over again, my legs still around her hips, and I found myself lying face to face on top of her, my hard erection pressing against her groin, still covered in the jean shorts.

"Getting a little eager, aren't you?" she asked. I nodded, and she sat back up, taking me up with her so that I was on her lap again, this time straddling her from the front. She ran her hands down my back, letting them come to a rest on my ass.

"Go fetch the strapon." she said. My heart skipped a beat.

"I thought..." I started, but then looked over at us in the mirror. There she was, powerful and strong and dominant, and there I was, soft and weak and submissive. Of course she belonged on top. I stood up and walked over to the door, watching Tana over my shoulder sitting up at the edge of the bed. I open into the drawer I had seen her pull the strapon out of three days ago.

As I reached down into the drawer to grab the strapon, I could hear her unbuckling her belt and dropping the shorts to the floor. I hurriedly grabbed the bottle of lube, my heart racing, and made sure to completely cover the strapon with it, adding much more than she had used last time. Then, taking a deep breath, I turned back to Tana. She was fully nude now, nothing hiding her powerfully-built body from me.

"Come help me put it on." She commanded. I obeyed without any argument, approaching her and kneeling at her feet, her thighs like tree trunks in front of me. I wrapped the belt of the strapon around her waist and began fastening it, looking up at her face. She smiled down at me approvingly.

James19999
James19999
342 Followers
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