Femboy Roommate (My)

My name is Brad. I'm in my mid-twenties, working my first job out of college in the big city. I'm fit but not big, 5'11" with short kempt brown hair.

I had been dating a girl named Amber for about four months now. She was a petite brunette with a bubbly outgoing attitude and the sex was great. Life was good.

My roommate Adam was moving out of our two bedroom apartment to take a job across the country. We hadn't been too close but he was a good roommate. The apartment complex would fill his room in time, however my next roommate was not what I was expecting.

Alex moved in soon after. We were the same age. She had chin length bleached blonde hair, green eyes and a tight body. She had pale skin, small tits, with a tight round ass to match. She was a bit effeminate. Alex was a sissy I'd guess you'd say. We got along fine, after the brief awkward new roommate phase. I was almost never home anyway, as I often stayed at Amber's a few nights a week.

Alex and I would chit-chat when at home, watch TV and joke like normal roommates do.

I got the feeling Alex was into guys. If the clothes didn't give it away, the make-up sure did, which didn't bother me. She mostly wore black or pink or both. Can you be goth and wear pink? I didn't know, shrug. She would wear eye liner and make her cheeks rosy. Alex would often put her hair in pigtails, like short springy tufts as she bounced around the apartment. Then there was the perfume. She smelled great and compared to a roommate that didn't do their dishes or laundry, sweet and tidy beats the alternative.

Alex would get dolled up when I was home to get a rise out of me.

She would catch me looking sometimes and would prance into the room asking, "How do I look?"

I would grin a grin that meant, I know what you're doing, and say, "You look nice."

In a pouty face and tone she'd comment, "Just nice?!" as she walked by, making sure I smelled her scent and saw the bounce of her tight curves.

On one occasion, Alex was dolled up in a sheer spaghetti strap tank top and mini skirt, with lace stockings. No bra. Her pink nipples were hard and hard on purpose. I was in the kitchen when she came bouncing in.

Our kitchen wasn't very big so she'd make sure to touch me in some way as she passed. Sometimes a hand on my lower back or on my shoulder. I'm not ashamed to say I liked the attention. Knowing that someone finds you attractive without saying the words, it was in the air. You could feel the sexual energy and she knew she had that power over me. She also knew nothing was gonna happen, so what does she have to lose in teasing I suppose.

Alex had the fridge door open and was bent over at the waist looking for something inside or waiting for me to notice. Her skirt rose up, almost revealing everything. This time I decided to play along. She sensed me approaching and I could see her ear wiggle, she was grinning.

"Oh excuse me, I'm just grabbing the OJ." I said.

She was still guarding the entrance to the fridge. I put my left hand on her waist as if to hold myself up as I leaned into her. My crotch now against her butt, my right hand brushing against her chest as I took the OJ. A girlish moan came from her lips.

"Hey watch it." she teased as she smacked my butt. (She knew she could get away with it.)

"Oh I am." I said as I gave her a wink and a smile.

I had never thought of her in that way but I had to admit she looked sexy right now.

Light flirting would continue through the weeks and I liked it. We had similar schedules and during the week Alex appeared androgynous to the outside world, wearing guy clothes. She hid her small breasts with heavy tops, layers or a jacket. We would both wear sweats and a t-shirt around the house. I would catch her checking out my ass as we passed each other and it would be hard not to notice her bulge waggle underneath her sweats.

Alex would often say, "I don't wear panties unless I have to."

So there wasn't ever much between her and me when at home. She kept me turned me on.

On another occasion, I was playing on my computer in my bedroom when she came in and plopped on my bed.

"I'm bored, play with me Bradly." Alex begged.

She was wearing socks up over her knees and a shirt that was too big falling down to mid thigh. I wondered what was beneath that shirt.

As if reading my mind, she pulled her right arm back into her sleeve and under her shirt. I swiveled my chair to watch.

"Do you want to touch me Bradley? I know you have a girl but that doesn't mean I can't touch myself." Alex teased.

She had my full attention. Her bright green doe eyes stuck on mine. She kept touching herself, underneath that shirt all while feigning normalcy.

"I always think about you when I touch myself Bradley." she whimpered.

What was happening?

She rose up on her knees at the end of my bed so that I could see and bent over, holding herself up with her left hand. She was ready for doggy-style.

Her shirt still covering her ass but inching higher with each movement, until finally her asshole peaked out. Her right arm was at work, stroking herself as she kept me in the corner of her eye. Was my jaw on the floor?

Alex moaned and writhed, simulating sex. She slammed her ass back into an imaginary cock. My cock. Rising back up, still on her knees, she turned her butt away from me. The front of her shirt came to a point, shaped by the tip of her dick and darkened by a small wet spot. I could see the slight motion of her rubbing her cock up and down. Her left hand now focused on her butt as she began fingering herself. Slowly she went, maintaining eye contact and biting her bottom lip in the cutest way.

Her forehead wrinkled with feeling as she moaned. My own sweatpants were betraying my poise. Before escalating further, she gave a long sigh.

"You tease me so Bradley, you're a bad boy. Goodnight!" she said and with a kiss on my cheek, she was off to bed.

Alex would say things, like "Where have you been?" with a smirk and fake jealous tone when I'd get home after a couple night stay at Amber's. "I've been lonely, I've missed you."

After a long weekend away Alex gave me a hug, and nestled her nose against my neck, taking in my scent. She slowly released me running her hands down my back. She had missed me indeed.

"You smell good." I said as she leaned back looking me in my face as she smiled, our waists still connected in the extended embrace.

She made sure to wiggle a little to make sure I could feel her, knowing that I knew she wore no panties.

"I have to smell good for daddy, I don't want to make him mad." Alex said.

She knew calling me "daddy" got to me, in a good way. Had I let this all go too far, I asked myself.

As we released each other I gave her a cynical "Mmhmm sure." A smile growing on my face.

"How do you like my outfit?" Alex teased as she spun and leaned back into me. She had her pigtails up, bouncing as she spoke.

"Good enough to eat." I said.

A sinister grin appeared on her face.

"Is daddy being naughty?" she pleaded.

She was wearing boy shorts with a v-neck tank top. Almost half of her pert ass hanging out of the bottom. Her pale skin was spotless and legs shaved clean. What else was shaved clean I wondered.

My dick jumped as she wiggled me in between her butt. Did she feel that, I thought. Her soft moan answered me. I slid my hands from her waist down into a V below her belly button, pressing her butt into me harder. This felt so good. What was I doing?

"I like when daddy gets naughty with me." Alex purred.

I released her, in a daze I plopped into a seat in the living room. She sat on the arm of the chair and put her arm around me, massaging my neck. I glanced at her chest as her v-neck tank top wasn't form fitting.

"You like what you see daddy?" she asked.

"Yea, I think you know I do, but nothing we can do about it." I said.

She sighed, in a teasing way, understanding what I meant. We were roommates and I had a girl. This didn't stop her from making sure I saw her ass as she went to her room, looking back to make sure I was looking. I was, she smiled.

It had been around the six month mark with Amber when our relationship just fell apart. We decided to end things mutually with no hard feelings. I decided to fill the void with a night out with some friends that weekend. I made it home around midnight. I was no lightweight, I wasn't sloppy, just had a real nice buzz.

Alex was up and a bit surprised I came home. She was beaming to see me and I was happy to see her too. Was she wearing my underwear? White Calvin Klein boxer-briefs, yep she was, and they looked perfect on her.

She could tell I was a bit tipsy and skipped over and jumped on me, squeezing me into her. She had a tank top on along with my underwear. She slid her hands into my back pockets as she leaned back taking me in. Our bottom halves still touching as she liked to do. She wiggled her waist against me.

"I'm wearing your underwear." she said.

"Yea, how come you wear them better than me?" I asked.

"Oh daddy, I don't know about that." she said grinning.

She moved her hands to the top button of my jeans. She gave a small gasp when she realized I wasn't stopping her. She looked up into my face as she unzipped me, a storm brewing in her blazing green eyes.

She nestled her nose against my neck as she had done many times before, her whispering against me, "Yes daddy."

My jeans dropped to the floor, Alex resumed pressing her crotch against mine. She slowly kissed my neck as she unbuttoned my shirt. My hands now grabbing her ass, pulling her even harder against me. I could smell her perfume and feel her heat.

With my shirt opened, she leaned back to take me in. Letting my shirt go, I spun her around, pulling her ass against me.

She moaned, "Yes." as my hands roamed underneath her shirt up her stomach, searching for her breasts. Her tits a handful, her nipples erect.

"I like to touch myself while wearing your underwear daddy." Alex confessed. "I've been bad, spank me please." she begged.

With my right hand I smacked her butt hard, the sound echoing through the apartment, and ending it with a handful as I squeezed her bottom.

"Mmmm." rose from her chest.

I lifted her shirt up and off as she swiveled around with her pouty eyes, a look pleading "I want you."

Her kiss was with intent, sweet and wet. Our naked chests flush, pressed hard against each other. I didn't want to be one inch away from her. We had waited a long time for this kiss, so it was only proper that it was a long make out.

Dry humping, our crotches rubbing intently against each other. Alex took her hands from around my back and slid them underneath the waist band of my underwear and dug her nails into my ass cheeks.

"Yes baby, I want you." fell from my lips.

Sober, I was now only intoxicated by her. She slipped one hand down my ass and found my asshole.

"I've never done anything like this." I said.

"I'll take care of you daddy." Alex breathed.

With her other hand she began to slip my underwear off and descend to her knees. Her left hand rubbing my asshole, her right hand on the base of my now throbbing cock, her eyes looking up to meet mine with pure hunger in her face. My mouth was watering.

My cock stood at attention at seven inches. She dove in eagerly, taking me into her mouth with a long moan coming from her throat. Stroking me now into her mouth, sucking hard, taking it slow.

With her left hand, a finger found it's way inside. I groaned in pleasure. After some time she stopped, knowing that the night was just getting started. The taste of my cock on her lips, she got up to her feet and took me by the hand.

"Let's get you to bed daddy." she purred.

Alex took me to her room. Me naked, her still wearing my underwear looking cute, her bulge enticing me. She turned, biting her lip in the cutest way, looking me in my face and slowly bending at the waist, sliding her underwear down. Her cock was just as big as mine and hard. I kissed her deep, our cocks pointing north, rubbing against our stomachs.

Alex crawled onto the bed on all fours, her ass pointing into the air as she leaned down on her elbows looking back at me. I grabbed the lube and stroked my cock with it from base to tip. Onto the bed I pressed the head of my dick to her entrance and rubbed it around the perimeter. Alex moaned deeply.

Slowly I entered, inch by inch, Alex moaning, "Yes daddy!" as I went.

I continued until I was in to the hilt. She felt so good. With my hands on her hips I stayed here until she was ready.

A slight "Mmhmm." and I continued back out and slowly in again. She was so tight.

As I picked up pace my balls began to slap against her. She began to push back into me, her ass greeting me hungrily. Light moans elicited from our passions, mingled in the air and danced together, mixing into a single note of pleasure.

After some time she stopped me and rolled onto her back so that we could see each other. I slowly pushed back into her as I took her into my hand, stroking her hard and pushing into her harder. Her perfume now mixed with our sweat.

"I want your cum!" Alex demanded.

The sensation arose and deep into her I came. Had time stopped? It had skipped at least as I began to see colors. Slowly I pulled out as she held onto what remained.

Both of our faces still filled with lust, I descended onto her. Taking her cock into my mouth, I stroked her and did what I knew would feel best. I didn't want this night to end. I choked, she giggled.

"I'm coming daddy!" Alex pleaded.

She tasted like candy. I swallowed her completely.

"I'd eaten Lemon Heads earlier." she explained.

I wasn't complaining. We laid there together, pulling the sheets over our tired bodies, arms and legs intertwined.

"You are absolutely singular baby." I affirmed.

"You're so silly Bradley." she teased.

We slept.