Study Group Surprise

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James explores his feminine side with his crush's roommate.
4.6k words
4.73
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Part 1 of the 2 part series

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

"Thanks for coming over, James. This was really helpful. See you next week?" said Mandy as she stood up, tanned legs visible below the cutoff of her short jean shorts. She looked down at me, smiling with her pure white teeth. I looked at her for a little longer than I should have before I realized I was supposed to reply.

"Yeah, definitely. I think this is going to be a good study group." I replied, feeling a twinge of embarrassment that I couldn't find something smoother to say. Mandy turned and walked toward the door. Once again, my eyes lingered on her, admiring her long blonde hair as it flowed down the back of her delicate figure.

"Have fun with Brad," said Tana. My heart dropped a little as I remembered Mandy already had a boyfriend. I could feel a wave of insecurity in the back of my mind, recalling that Brad was a D1 baseball player with a chiseled jaw and probably a body like a Greek statue. I was certainly no athlete.

"I will!" called Mandy as she walked out the door of the apartment. I couldn't see her face, but I could imagine her smile, and it filled me with jealousy to know it was meant for someone else.

After the door closed, I turned back around, looking at Mandy's roommate, Tana, across the table from me. The two of them couldn't have looked more different. Mandy was a stunning, classically beautiful girl with blonde hair and blue eyes, and a slim but curvy figure like you'd see on a Hollywood actress. She was always the hottest girl in the room, and I couldn't help but feel my heart flutter whenever I saw her.

That wasn't to say Tana was ugly, but she wasn't the radiant beauty Mandy was. Tana was a big Samoan girl, almost six feet tall with long black hair, mocha-colored skin, and a broad, flat nose. Today, she was wearing a tank top that left her large, round shoulders and thick arms exposed. I'd always found her a little intimidating, but today, as she looked across the table at me, I saw a trace of amusement in those brown eyes of hers.

"You sure like looking at her." she said, that same amusement in her eyes appearing in her voice now too. I felt my cheeks heat up a bit. Was I that easy to read?

I looked back at Tana for a moment, trying to come up with a clever reply, but my mind stayed frustratingly empty. Tana let out a little giggle.

"What?" I asked, accidentally letting a hint of annoyance creep into my voice.

"That's why you started this little study group, isn't it?"

"Hey, organic chemistry isn't easy, I thought it would help to have someone to bounce ideas off of." I knew it sounded unconvincing as I said it, but I couldn't help myself. I've always been bad at poker.

"I mean, you're not wrong about that. And I learned a lot today too. But I just don't want you to get your hopes up too high and get disappointed." She gave a suggestive glance toward the door that Mandy had just left through. "You know Brad, right?"

I did know Brad. I knew his perfectly square jaw line, his angular facial features, his bulging arms, the way he towered over me, and worst of all, the way Mandy looked at him so adoringly. "What are you getting at?"

"Mandy has a type." Tana looked me up and down. "And you're...."

Not it. She didn't say it, but I could tell what she meant, and it stung. I looked back at her, irritated but knowing deep down she was right, which only made it worse.

"You never know."

"Come on, she likes athletes. Strong guys." Tana paused for a moment, a slightly mischievous look on her face. "I bet $20 you couldn't beat me at arm wrestling."

I felt my cheeks heat up. I couldn't just let her challenge me like that.

"Oh yeah?" I blurted out. "Let's try it."

Tana grinned and slid her arm across the table, pushing our books and notes to one side before putting her elbow on the table, hand reaching across to me. I set my own elbow down and grabbed her hand. Looking at our arms, I immediately realized I had made a mistake. She was right; I hardly ever worked out, and I definitely wasn't a strong man. Her upper arm was much thicker than mine, and it wasn't just fat. Seeing her biceps flex as she positioned herself, I was more aware than ever that there was a strong layer of muscle there.

But now it was too late to back down. "Ready?" She asked. "Let's go." I replied, trying not to sound nervous.

My teeth clenched and my scrawny biceps flexed as I tried to pin her hand, pushing it toward the table with the strength I could muster. She looked directly back at me, her face hardly showing any strain as she slowly but surely forced my hand the other way. Within just a few seconds, I could feel the back of my hand hit the wood. She flashed that amused smile at me again.

"Fuck." I said, reaching down toward my pocket with my unpinned hand.

"Wait." replied Tana, still holding my right hand down on the table. I looked at her, the smile on her face widening just a bit. "You can keep your money. There's something else I want instead."

I could feel a wave of unease coming over me as I watched her face, noticing a distinct look of mischief in her brown eyes. My own eyes narrowed, and I stopped reaching for my pocket.

Tana stood up, letting go of my hand and turning to walk toward a door at the side of the room. My apartment had the same floor plan, and I knew the door led to the closet with the washer and dryer. I stood up and walked around the table to get a closer look at what she was doing. She reached into the drier and tossed me a red bundle.

I caught it and looked at it more closely. It was stretchy and smooth, some kind of polyester. I unfurled it a bit more and realized I was staring at a bikini.

"Try it on."

"Is this Mandy's?" I asked, amazed I could manage to get words out at all.

"Well, I don't think one of mine would fit you." replied Tana with a smirk.

My heart was pounding now, and my cheeks were burning. I couldn't believe she was asking me to do this. I shook my head.

"Nevermind, I think I'll just give you the $20." I said.

"Come on..." wheedled Tana, looking at me with a pout. "I bet you'd look good in it."

I opened my mouth to say no, but something stopped me. I thought of Mandy, and how I'd love to see her in this skimpy swimsuit. Tana was right, though: Mandy did have a type, and she wouldn't wear something like this for me. Maybe putting it on myself was the closest I'd get...

"I promise I won't watch you change." said Tana, walking over to the front door and stopping right in front of it, hands on either side of the frame. There was no way I'd be able to walk out of her without her permission.

Fuck it, why not. My heart raced as I unzipped my jeans and stepped out of them, and then my boxers. I slide the red bikini bottoms up my legs, pulling them over my privates. My dick hardened at the twin thrills of wearing something of Mandy's, and the transgression of doing it without Mandy knowing.

Next, I pulled my shirt off over my head and looked down at the white polyester bikini bra in my hands. I put the cups over my flat chest and grabbed the strings, pulling them around my back. I fumbled around blindly with them for a few awkward moments, not getting any closer to tying the knot.

"Need help with the strings?" I noticed Tana had turned around and was looking at me, a grin on her face. I flushed bright red as she looked me up and down, grin growing wider and a little more wolfish.

I tried to stammer out a reply, but nothing useful came out. Tana crossed the room, stopping just a few feet ahead of me. She was a good three or four inches taller than me, looking down into my eyes.

"Turn around." she said. I looked up at her for a moment but couldn't take her brown eyes fixed on mine. Besides, I was getting nowhere with the strings. I turned around, looking toward the window. Thankfully, the blinds were down, so no one could see in.

I felt Tana's touch on my back as she tied the strings in a few adept motions. Then, I heard her giggle.

"What's so funny?" I asked, feeling more than a hint of nervousness.

"You have a better ass than Mandy."

I spun around to face Tana. She was holding back another giggle, I could tell.

"Now you're just making fun of me." I said, feeling ridiculous in the tight white bikini, practically naked in front of a woman I knew was much larger and stronger than me.

"I'm not!" she replied, her early pout returning to her face and voice. "Let me show you." Before I could respond, she slipped her hand onto the small of my back and turned me toward her bedroom. She gave me a very gentle push, and I started walking, her hand still on my back as she walked beside me.

Tana guided me into her bedroom. We stopped in front of a full length mirror on the wall. I closed my eyes, scared of what I might see. After pausing to take a breath, I made myself open my eyes.

There I was. I saw the red bikini hardly covering any of my slim figure, my pale skin practically all bare, my thin blonde body hair barely visible. My waist tapered so it was just a little thinner than my hips, hardly any hair visible on my flat stomach. My thighs were slender and had a gentle curve to them. I turned a bit, and saw how round my butt looked with the bright red polyester leaving the outer part of the cheeks exposed. It probably didn't help that I had a full erection pulling the skimpy material of the bottoms toward the front, even if it was only four inches long. To my shock, my face was not quite as red as the bikini, but I was blushing.

Tana stood behind and beside me, looking like a giantess in contrast to me. Although she was only four inches taller than me, her shoulders were easily as broad as mine, and her bulging upper arms were almost as big as my thighs. She didn't have a manly face, but her broad, flat nose and thick lips did strike a real contrast to my own delicate facial features. Her long black hair flowed down, my light brown, almost blonde hair shining in the light.

She slid her right hand from the small of my back around to my side, mocha-colored fingers digging into my soft, pale skin as she pulled me closer. Stepping up just behind and beside me, I felt my back pressed against her chest, only the cloth of her tank top standing between my skin and hers. I could feel her breast against the back of my left shoulder, and my butt against her thigh.

My heart beat even faster, and Tana smiled as she looked at us in the mirror.

"See? You may not be Mandy's type, but you are mine."

"Wha-" I started, before I felt her abruptly spin me around. She pressed herself against me hard, and I lost my balance, falling back a couple inches until my back hit the wall next to the mirror. I reached out for something to steady me, my hands catching her shoulders. Under a layer of fat, I could feel her powerful delts under my hands as she pressed herself up against me, pinning me to the wall. My body rubbed against hers, feeling strong, heavy muscles pushed up against me.

Tana leaned her head down, and before I knew what was happening, her lips were on mine. She hungrily kissed me, teeth brushing against my lower lip. Her hands ran down from the bikini strings across my sides and down to my hips. Before I could pull away, she grabbed the undersides of my thighs and lifted, and I found my legs wrapped around her waist. I could feel her obliques on the insides of my thighs and the contours of her abs on my dick.

She stepped away from the wall, carrying me with her. With her hands under my legs, my lower body was steady, but I could feel my upper body falling. Before I even knew what I was doing, I threw my arms around her neck, coming to a rest on her sloping traps, pulling me tight against her for stability. Not a single part of me was touching anything but her, but she carried me effortlessly. I felt helpless and disoriented, but also somehow safe pressed up against her strong, solid body.

The kiss ended and she pulled away, her eyes meeting mine. My heart fluttered as I saw her smiling. She turned around, my legs still wrapped around her waist and my arms still around her neck. I caught a glimpse of us in the mirror, my pale, slender body clinging tightly to her solid form. Then, she gently set me down on her bed, letting go of me but still leaving my legs around her waist.

She leaned into me, pinning me onto the bed, her waist between my legs. My heart raced and my dick was like a rock as she leaned down and kissed me again. I unwrapped my arms from her neck and ran my hands down her arms, feeling her bulging triceps under her smooth skin as she pressed herself down on me. After our lips were locked again for a moment, she pulled back again and stood up, easing out from between my legs and leaving me lying on the bed.

I sat up, looking up at her. Sitting down while she stood, she towered over me even more. In the mirror, I could see myself sitting propped on my elbows, looking dainty and small next to Tana's powerful standing body, still dressed in her tank top and jeans.

"I have a surprise for you." she said. "Lie face down on the bed and close your eyes."

"What is it?"

She snapped her fingers and pointed at the pillow. Although my heart race pounding so hard I could hear it, I obeyed her and rolled over, pressing my head into the pillow and closing my eyes.

I heard her footsteps padding away from me on the carpeted floor. After a moment, curiosity got the better of me and I turned my head and opened my eyes. She had walked across the room to her dresser and was standing with her back to me. She lifted the tank top off over her head, the thick muscles of her upper back dancing under her skin with the movement.

I couldn't take my eyes off her as she reached down and unbuttoned her jeans before sliding them down. Her thighs bulged, and although the layer of fat over the muscle gave them a smooth, rather than toned, appearance, I could tell they were extremely strong. I was mesmerized by her body, which managed to have a femininity about it even though she looked strong enough to wrestle a bear.

Without bothering to take off her bra or panties, she began wrapping a harness around her waist. I leaned up on one elbow, trying to get a better look. Forgetting her earlier order to lie down with my eyes closed, I watched her intently for a few seconds.

She turned around. Her bra was still on, obscuring what were probably B or C cup breasts. The way her body twisted, I could see the centerline of her abs, though the full shape of the six-pack wasn't visible under the layer of fat. My eyes ran down her torso to her hips and went wide as I saw what the harness was for: a six-inch black strapon.

"Didn't I tell you to lie down?" she asked, taking a step across the room toward me.

"What is that?" I asked, eyes fixed on the strapon.

"What does it look like?" Another step.

I sat up on the edge of the bed. "What are you going to do with that?"

"You're the smart one in the study group, you tell me."

I gulped as I stared at the six-inch toy. She was still walking toward me, only a few steps to go. I was sweating now and my heart was pounding, but I felt frozen and couldn't bring myself to move. Tana approached further and finally stopped, her hips brushing the inside of my knees. I sat on the bed, eyes still fixed on the strapon.

Tana slid her hand under my chin and tilted my head up, looking down into my eyes.

"Well? What am I going to do with it?"

"You're going to fuck me," I blurted out, half question and half answer. She smiled at me wickedly.

"Well well, you always do have the right answer. Now, lie down like I told you." She slid the hand that was on my chin down my neck and onto my shoulder. My heart was pounding in my ears. But for some reason, my erection seemed even stronger.

"Wait!" I said, breathing heavily. Tana paused for a moment and looked down at me quizzically. I hesitated and tried to open my mouth, but nothing came out. I tried again; a useless stammer was all I could manage. Finally, after what felt like an eternity, I was able to make the words form.

"Be gentle." I said, shocked at what came out of my mouth. Not "no," not "I don't want to do this," but "be gentle?" What the hell was wrong with me.

Tana giggled. "I don't know..." she said playfully. "You didn't listen when I told you to lie down. I think I need to show you who's boss." She flexed her quads, showing off the powerful muscles.

"Wait!" I said again. She still look down at me, clearly waiting for something again. Acting on an instinct I didn't even realize I had, I slid down from the bed, kneeling at her feet. The strapon was eye level with me, just a few inches from my face. In the mirror behind me, I could see my small, slender form kneeling in front of Tana's huge legs, each of her thighs almost as thick as my waist.

I bent down and pressed my lips to the top of her bare foot. Then I kissed her ankle, and started working my way up. I felt the rock-hard muscle of her calves under my lips, then her quads and hamstrings as I kissed my way up her leg. As I got near the top, I rested my lips against her hip, leaning my whole body against that tree trunk of a leg, looking up into her eyes.

"Please."

"Well, since you asked so nicely..." she said, grabbing me under the arm and pulling me to my feet. She gave me a gentle push onto the bed.

"Now, roll over for me."

Without hesitating, I did as she commanded, rolling over on the comforter, my face buried in the pillow and my dick rubbing against the top of the bed. She climbed on top of me, her thighs straddling my waist and her hands touching my shoulders. She reached down and grabbed the bikini bottoms. Instinctively, I lifted my hips to let her slide them down to my thighs.

I felt her let her whole weight down onto me, her thick torso pressing me down into the bed, her legs straddling me from behind, and the tip of the strapon teasing my ass cheeks. Her long black hair fell down around my head as she leaned down and kissed my earlobe.

"Ready?" she whispered. I let out some kind of noise between a grunt and a whimper, and I felt the tip of the strapon enter me. I couldn't help but let out a little gasp of pain as it stretched me. It went in deeper, and my gasp became louder. Finally, I felt her hips pressed against my buttocks. It was all the way in.

Tana slid her hands down my arms, then interlaced her fingers with mine. Another soft kiss on the ear, and I could feel her pulling slowly back out. Then, sliding gently but firmly back in. I let out another little gasp, this one softer than the one before. Although I could still feel a bit of pain as the strapon stretched me, the way Tana held me made me feel oddly safe, as if cocooned between the softness of the bed and the softness yet firmness of her body.

She began to thrust in and out at a gentle rhythm, and a wave of pleasure radiated from my butt outward toward my dick, which was also being rubbed against the bed as her thrusts pushed me down. Before I knew it, a moan escaped my lips.

"Who's your daddy?" she asked.

"Uhh" I moaned back, eyelids fluttering.

She thrust in a little harder, bringing a spike of pain but also of pleasure.

"You are!" I almost shouted in shock

"Good girl" she purred, resuming the previous rhythm, letting out the occasional grunt as she used her powerful hips to drive the strapon into me again and again. Soon I found myself moaning again, the pleasure from her thrusts making my whole body feel light and tingly. Tana picked up the pace just a little more, and I realized I hadn't managed to shut my mouth for the last minute.

A sudden spasm wracked my body, and I realized I was already almost at orgasm. I clenched for a moment and then gave up, surrendering to the gentle but firm thrusts deep into me, pounding my prostate. I let out my loudest moan yet as my whole body shook, and felt a sudden splash of heat on my groin and lower stomach, dimly aware that I just came. My eyes rolled back in my head and I trembled, feeling the orgasm through my whole body.

James19999
James19999
342 Followers
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