My Senior Year of College Ch. 01

I was sitting on the edge of my bed, wearing just my blue panties, a matching bra, and a pair of black platform pumps. My dress was in a puddle on the floor where it had fallen as we kissed. Bobby's shirt was off, exposing his hard stomach, and his jeans were around his ankles. His cock was just inches from my face, throbbing with the beat of his heart. This was one of the sexiest moments of my life, I thought, as my hand reached out and wrapped around his shaft. I gave it one stroke, and another, then leaned forward to kiss the tip. A drop of precum stretched between my lips and his dick as I pulled away. I looked up into his eye, smiled, then opened my mouth and let his hard cock slip between my lips for my first ever blowjob.

I placed my hands on his hips and drew him toward me. The head of his cock pressed against the back of my throat and I gagged a little, but when I pulled back I was fine, so I kept sucking. Each time it hit my throat it bothered me less, and after a while there was no gagging at all. I tried to open myself to deep throat him, but I couldn't manage it. That was fine, though, because the feel of his shaft passing over my tongue as he rocked his hips back and forth made me feel like a real woman.

After a few minutes of this, Bobby grabbed a handful of my hair and pulled my head into his crotch. I felt his cock pulse at the same time I felt the first spurts of cum splash into my mouth. His hips bucked as he came, and his cock bumped my throat. I swallowed some of his juice, but he came so much that a lot of it dripped out the corners of my mouth. It tasted salty and musky, and I closed my eyes in ecstasy, savoring the flavor, rolling it around my tongue, feeling it slip down my throat and drip from my chin.

When Bobby finished his orgasm, he squeezed out a few last drops by grasping the base of his dick and pushing toward the tip, then he pulled it out of my mouth. I gazed up at him, my first sexual encounter as a girl, and smiled. He smiled back and reached out a finger to wipe some of the goo off my mouth. I grabbed his wrist and put the finger in my mouth, tasting him afresh, sliding my tongue around his knuckles. I pulled my head back and his finger popped out of my mouth with a wet noise.

Bobby sat next to me, kicked off his jeans, and put an arm around my shoulders. He pulled me close and kissed me, his tongue pushing past my lips as his cock had just a few moments before. He must have tasted his own cum, and the idea of it made me even hotter. We kissed for a time, then he looked into my eyes with our noses almost touching.

"Do you want me to do you now?" he asked softly.

I nodded, too nervous to say anything. Bobby smiled again, slid off the bed, and went to his knees before me. He slid his big hands up my thighs to the waistband of my panties, hooked his fingers around them, and pulled them down. My little cock sprung out. I had never seen it so hard and swollen. Bobby slid my panties down my legs and I lifted my feet so he could pull them off completely. He leaned in and licked my hairless shaft from base to head, then positioned his mouth over the tip. He raised his eyes to meet mine, then opened his mouth and took my entire penis into his mouth in one motion.

It felt so good, so much better than when girls had done it. I tangled my fingers in his short hair, not to direct him but just to feel more connected to him. I let him control the speed he sucked my dick. I stretched my legs out to either side of him, resting my feet on the heels of my pumps. Bobby slid one hand around to the small of my back, caressing my skin with his fingertips, rubbing around in small circles. I was so hot and excited that I couldn't last. In less than a minute I was cuming. A small feminine squeal escaped my lips as my seed pumped out. Bobby swallowed it all, and when I was done coming he slid his body up mine, pushing me back on the bed until we were face to face.

"That was fantastic," he said. I could smell my cum on his breath. "Can I stay here tonight?"

"Yes," I whispered. "I'd like that." My arms wrapped around his neck and I pulled his face down for a long, passionate kiss. I kicked off my heels and we both lay down on the bed. Bobby pulled the sheets up over our bodies, and I fell asleep wrapped in his strong arms.

I woke as the sun was coming up. A shaft of golden light came through the gap in the curtains of the window in my bedroom and fell across my face, partly blinding me. For a moment I didn't remember last night, but then I noticed Bobby's arm draped over me. I smiled fondly at the memory of him cumming in my mouth. I must have rolled over in the night, because although I was still in his arms, Bobby was now spooning me. I could feel his soft cock pressing against the small of my back. It made me feel warm inside, knowing he stayed the night with me.

I met Bobby last night at a party. It was the first weekend of the fall semester, and this was the first time I was attending school as a coed. I had come down and rented this apartment in June, got a job as a waitress at a bar, and registered for classes all as Evelyn instead of Evan Ross. I was feeling lonely, so when I saw a flyer for the party I decided it would be fun to go out and meet people as a girl.

I had been a small boy my whole life, and puberty hadn't changed that. I was small and boyish, so when I started wearing women's clothes as a teenager I looked less like a crossdressing man and more like a boyish girl. All through high school I dressed up whenever my parents were out of the house, and when I went to college I got a job and an apartment after the first semester so I could have more privacy than I did in the dorms to wear women's clothes.

After two years of part time crossdressing and a few mediocre relationships with girls, I realized that more than anything I wanted to be a woman. I went to therapy for a year, and in the Spring was finally ready to start my transformation. Now starting my senior year of school, I felt more alive than I had before, although more alone than before, too. I hadn't had many friends, and the few I had made in the first three years of college stopped returning my texts and emails when I started my transformation.

The party was in a house shared by some lacrosse players. It was only a few blocks from my apartment, so I felt that if I wasn't enjoying myself or if I felt uncomfortable I could always just leave and be home in a few minutes. I dressed carefully, knowing this would be my first night out as a girl. First I warmed my breast forms, and put them on, hiding the seam where they met my skin with foundation. When that was done, I put on a blue lace bra and matching boyshorts, and put on my makeup. I never wore a lot of makeup, just a little foundation and blush, then eyeliner and mascara. Tonight, though, I followed that with dark eyeshadow and pink lipgloss.

My dress was a dark blue knit a-line dress with short sleeves and pleats in the skirt. It had a scoop neckline, and I chose a silver chain with a heart pendant to go with it. I put on silver hoop earrings, then picked out a pair of black platform heels which were comfortable enough to stand around in all night. I looked in the mirror one last time, finger brushed my hair behind my ear and put on a white sweater, then headed out.

When I walked in the first thing I noticed was all the boys staring at me. I experienced that at the bar sometimes, but here it was different. At work it was creepy, with all those strangers seeing me as a piece of meat whose only purpose was to look good and bring them food and beer, but here at the party I felt sexy. The eyes of all those boys on my body made me feel desirable instead of dirty, and I really liked the sensation.

I drank and danced for a few hours, feeling good about myself as a college girl. Then just as I had decided I'd had enough and was ready to leave, Bobby came in. He was tall and muscular, with short blond hair that had just enough bangs that I felt I needed to brush it away from his light brown eyes. He must have felt my eyes on him, because he looked over at me and smiled. I smiled back and dropped my gaze, light headed and with butterflies starting in my stomach. When he came over and asked me to dance, I couldn't find my voice. I just nodded and smiled shyly at him.

Soon we were dancing, and when the music changed to a slow dance we started kissing. Lightly at first, but then with more passion. Soon we were barely swaying to the music, just rocking back and forth, our arms wrapped tightly around each other as our tongues entwined. When Bobby suggested we go somewhere more private, I hurriedly agreed. We left the party hand in hand, only stopping long enough for me to grab my sweater from the couch by the door.

Once outside I remembered I wasn't really a girl. Being in Bobby's arms had felt so good that my thoughts and feelings had been entirely feminine, and I forgot about my secret. I stopped short half a block from the party as it hit me - if he knew that I was still physically a boy, he would probably be disgusted with me.

"What's wrong?" he asked, turning back to face me.

"I, I ..." I couldn't find the words to explain what I needed to explain. I felt tears welling up in my eyes.

Bobby put his hands on my shoulders. "Evelyn," he said, "it's okay. I know you used to be Evan."

My eyes went wide and I gasped. "How did you know?" Here I was priding myself on how girlish I had become, and the very first boy I kissed saw right through me.

Bobby looked in my eyes. "We were in freshman orientation together. I remember seeing you and thinking it was a shame you were a boy. I thought you would have been better as a pretty girl than as an effeminate boy." He grinned and wagged his eyebrows. "I didn't realize just how pretty you would be as a girl, though."

I rolled my eyes at his lame flattery, but inside I was singing. I didn't remember him at all, but that was to be expected. Orientation at a school with twenty thousand students was a big class. I still appreciated the sentiment. I smiled, grabbed his hand, and we went back to my apartment.

Now here I was wrapped in his arms, with his cock pressed against my back. I snuggled back, closer into his embrace, and sighed contentedly.

My motions woke him. He ran his hand up my arm and across my shoulder to my neck. His dick started getting stiff as he brushed my hair away from my neck and planted a kiss in the hollow below my jaw line. I drew in a shuddering breath as his hand slid down my side to my hip. It traced little circles there before moving around to my front and playing with my cock. He was hard before I was, and I felt him shift to get more comfortable while he jerked me off. I got fully hard soon after I felt that, and before long my cum was dripping from his knuckles as I shook in orgasm. He held his hand up to my face, and I licked his fingers clean, savoring the taste of my own cum.

By now Bobby was rock hard. "Get on your stomach, Ev," he told me. I rolled over and rested my head on my folded arms. I closed my eyes as he propped my hips up with a pillow. I knew what was coming next, and I was nervous. I had never had anything up my ass, and I knew his penis was going to be too big and would hurt as it went in. But I wanted it so bad, my whole body ached so much with the desire to have his cock inside me, that I was going to grit my teeth and bear up with the pain.

Bobby spread my cheeks and kissed along the crack of my ass. When he reached the bud of my asshole, his tongue snaked out across it, sending shivers up my spine. Then he continued kissing up and down the crack, each time licking the hole as he went past. I was breathing heavy, and I could feel my cock stirring, even though I had just cum. When Bobby stopped kissing and just concentrated on licking my hole, I moaned with pleasure.

He ran his tongue around the rim for a while, and started poking at my hole with his stiffened tongue. In short order his tongue was past my sphincter, swirling around the inside of my ass. The sensation was incredible. When he pulled his tongue away I whimpered and pushed my ass up toward him for more attention. He complied by slipping a finger inside and pumping it in and out. I felt him dribble saliva down my crack, and then felt a second finger probing at the entrance. It was tight at first, but I soon relaxed and his fingers were gliding in and out with ease.

By the time he used a third finger I was moaning and humping my hips against the pillow beneath me. I was ready for his cock and I told him so. He removed his hand from my bottom and I was left empty and gaping, but only for a few seconds. I felt him get up on his knees between my legs and then the tip of his cock was pressing where his fingers had been. I tensed up, but he made comforting sounds and kissed the back of my neck until I relaxed again. Then he pushed.

When the head entered me I screamed in a mix of pain and pleasure. Bobby stopped so I could get used to the size, and when I was ready I pushed my ass back toward him. I felt his shaft slowly enter me, that same sensation of hurt and ecstasy driving my libido crazy. It seemed to take forever, but eventually he was all the way in, his crotch pressed up against the curve of my ass.

He paused again, then started to pull out until only the head was inside me, then he pushed back inside. His strokes came faster and faster, and soon his hips were slapping against me, driving my face into the mattress. My hands clutched the sheets, holding on tight as Bobby fucked my ass. I grunted every time he pounded into me, as then I felt him stiffening. His thrusts became irregular, and then I felt his cum drench my insides. With a long, loud groan Bobby came and came, then collapsed on top of me, his dick still deep in my bowels.

We lay like that a while, his weight pushing down on me, and a deep throbbing in my bottom. He softened, and when he popped out I let out a little grunt of disappointment. Bobby rolled off of me, and pulled me into his arms.

"Oh, Evelyn," he said, "that was fantastic." He kissed my forehead, then my lips.

I put my arms around his neck and squeezed him tight. "Thank you Bobby," I said into his shoulder. "Thank you for making me a woman."