My Senior Year of College Ch. 02

The day after I slept with Bobby was great right from the start. After he left I imagined I could still feel his cock in my ass, and I could almost taste his cum on my tongue while I showered and got dressed. Normally I dress to avoid attention at work, but today I was feeling sexy and desirable so I dressed accordingly. The dress code for the wait staff was casual, so long as you wore black, but feeling as I did I decided to dress up. I picked out a black blouse with sheer sleeves and a black pinstripe pencil skirt with black tights and a pair of black patent pumps with four inch heels.

I had only been on hormones a month, so my breasts hadn't developed yet. I looked forward to the day I would no longer need to put those damn breast forms on. After they were on firmly I hooked my pushup bra beneath them and spun it around so the cups were in front, then settled them around the breast forms. I put on the matching panties, then sat on my bed and gathered one leg of the tights together and pulled it up my leg, repeating the process with the other leg. I fixed the seam on the toes and stood up to pull it the rest of the way over my hips. I stepped into the skirt and pulled it up, zipping up the side and pulling at it to straighten it. I stepped into the pumps, then went to my vanity to put on makeup. First was foundation to disguise the seam of my breast forms, then powder on my face, followed by eyeliner and mascara. I finished off with a little maroon lipgloss. My fingernails were trimmed and neat, but only had clearcoat on them. I glanced at the clock, thinking I might put polish on, but there wasn't enough time before I had to leave for work.

I put on the blouse and cinched it with a thin white leather belt. I finger brushed my hair, tilting my head back and shaking it so the hair would fall out straight. That gave me just the right tousled look. My hair still wasn't as long as I would like it, but it was in great condition and it always looked just how I wanted without having to do a lot to it. I gave it a little hairspray and was ready to go to work. On the way out the door I grabbed my denim jacket and put it on.

As I walked the five blocks to the bar I felt like I was on cloud nine. The click of my heels on the sidewalk was a constant reminder of my new femininity, and the stares from the men I passed told me how sexy I looked. I breezed in the door, grabbed my apron, and started to work.

The evening passed in a dream. Instead of feeling dirtied by the constant flirting and, as the men got drunk, the rude come ons, I felt empowered. All these men wanted to fuck me, and I had to admit, a small part of me wanted to fuck all of them. I smiled at them when they complimented me, I flirted with some of the cuter ones, and halfway through the night I had more in tips than I had ever made in a full shift.

I went to the storeroom for my break, sitting on a full case of beer and taking off my shoes to massage my feet. I hadn't been so smart with my shoe selection as I had been the night before, and although they looked hot, they were not comfortable for waitressing. But it was almost worth the pain, I said to myself as I thought about the tips I'd made.

As I sat there rubbing my feet, Jessie came in the storeroom. "Hey Ev," she chirped as she sat on a box next to mine. "How's it going?"

"Pretty good, thanks," I replied.

Jessie was wearing black boot cut pants that were tight around her hips and thighs, but flared a bit at the hem. She wore them with low heeled leather booties. She had topped it off with a thick cotton sweater that fell below her hips. Her long blonde hair was pinned back out of her eyes, but hung straight down her back.

"You look great tonight," she said. "That's a very pretty blouse."

I smiled. "Thanks."

"Feet hurting tonight?" she asked, nodding at my feet in my hands.

"Yeah, these shoes look great, but they weren't made for this kind of work," I said, scrunching up my face.

Jessie grinned, then scooted closer and held out her hands. "Here, let me do that." She took hold of my left foot and massaged it. She started at the toes and rubbed them for a minute, then dug her thumbs into the ball of my foot.

A soft moan escaped my lips as my eyes fluttered shut. Her hands worked away all the aching soreness from my feet - the ball, the arch, the heel, the ankle. In just a few minutes my left foot was done and I felt like I hadn't been standing all afternoon in heels. Jessie did the same for my right foot, and when she was done it was like the tension had been massaged out of my entire body, not just my feet.

"Oh, your hands are magic," I said when she put my foot down. "Thank you so much. I owe you big time for this."

"My pleasure, Ev," she said with a grin. "Say, do you have plans for after work? Maybe we can hang out and have a few drinks."

"Okay, sure," I replied. "That'd be great."

She smiled and stood up. "I've got to check on my tables. I'll talk to you a little later."

I glanced at my watch, and realized my break was almost over. I got up too and went back to work.

It was strange having Jessie invite me out that night. She had never even looked at me before. Not that she was rude to me, or ever snubbed me, it just seemed like I didn't exist for her. But after talking to her a bit, I was looking forward to getting to know her better. As I took care of my tables, I noticed her looking over at me whenever she was around. Every time I caught her looking, she flashed me a smile.

Finally our shift ended. I grabbed my jacket found Jessie waiting for me outside.

"Hey Ev", she said coming over to me. "Ready for those drinks?"

"Yeah, I sure am." Fifteen minutes later we were in her apartment sipping vodka and cranberry drinks on the couch. We chatted about work and boys, and I told her about my night with Bobby.

"Oh," she said with a mischievous grin, "Is that why you're all dolled up today?"

"Yeah," I admitted sheepishly. "I was feeling pretty and sexy today, so I dressed the part."

"Well you look the part," she said, sliding closer to me. Jessie put her hand on my knee. "You look gorgeous tonight."

I took a big gulp of my drink, feeling uncomfortable and excited at the same time. Jessie was a beautiful girl, but what would she think when she found out I was still a boy down there? "Um, look Jessie --"

She put her fingers on my lips. "Shh, I know what you're going to say, and it's okay. I'll only go as far as you want me to go."

"No, it's not that, it's --"

"Shh, just relax." She leaned in and planted a kiss on my mouth. Just a soft kiss, our lips barely touching, then she drew back.

I was stunned and breathless. I panted to get air into me, my chest rising and falling. Jessie was a tall, curvy blonde and looked as sexy as I always wished I did. But there was the little problem of my penis.

"Jessie," I began, but she put her fingers on my mouth again. They lingered there, caressing my lips. My eyes fluttered and I took a deep breath before she leaned in and kissed me again. This time it was a more forceful kiss. She ran her tongue along my lips, but didn't quite push it in, even when I opened my mouth.

She pulled away and looked at me, gauging my desire to go further. I put my hands out to stop her from kissing me again, but in my buzzed state I instead placed them square on her breasts. They were firm and large under her bulky sweater, and now she was breathing heavy along with me. I could feel my dick stirring under my skirt, and I knew I had to stop and explain before she found out.

She leaned in to kiss me again, her lips parted already, but this time I managed to stop her. "No, wait. I have something I have to tell you." She didn't listen to me, coming in for the kiss. I turned my head away, but she just nibbled on my neck, tracing her tongue along the line of my jaw.

"Oh, Jessie," I moaned. She pulled away far enough to look into my eyes, our noses touching.

"What is it you want to tell me, Evelyn?" she asked huskily.

My mind was foggy from the alcohol and the kisses. Jessie's big green eyes bored into me. "I have a penis," I whispered.

She pulled her head back. "Huh?"

"Don't be mad, I just didn't expect this to happen, and you're so pretty I couldn't stop it, and I don't --"

She stopped my words by planting her lips on mine again. "It's okay, Ev," she said. "You just took me by surprise, that's all. It's actually kind of a turn on." She smiled at me and said softly, "Can I see it?"

I nodded and stood up. I was almost fully hard, and it was uncomfortable tucked away between my legs. I unzipped my skirt and let it fall to the floor. Then I reached into my tights and panties and pulled my dick free. I tucked my underwear beneath my balls and stood there in my four inch pumps with my cock pointing straight at Jessie.

Still sitting, she reached out a hand to grab it, wrapping her fingers around the little shaft. "It's so cute," she said. "Do you want me to suck it?"

I nodded and took a step closer to her. Jessie pushed a strand of her long hair behind her ear and leaned in. Her breath was warm on my dick as she paused. She looked up at me, our eyes locking together as her mouth opened and she took me in. I watched as her red lips slid up and down my cock, from the rim of the head down to the base.

After a few minutes she let me slip out of her mouth and she stood up. Without a word she took my hand and led me to her bedroom. She pushed me down on the bed and straddled my legs with my little cock was trapped between us. She started grinding her hips, rubbing her pants on my dick. She pushed on my shoulders until I fell backwards, then she got on her hands and knees and, still straddling me, kissed me. She forced her tongue between my lips and swirled it around my mouth, her long blonde hair falling over my face.

I grabbed her hips, then slid my hands up under her sweater. I caressed her back as she pressed her lips against mine, until she sat up and pulled her sweater over her head. She was wearing a white satin bra with a pink bow between the cups. I reached up and unclasped it, letting her full, milky white breasts fall free. The nipples were small pink nubbins, fully erect, with a small areola around each one. I pulled her torso down so her nipples were close enough that I could stretch my neck and fasten my mouth around one perfect little bud. I rolled her nipple around in my mouth, eliciting little grunts and moans from her.

Then Jessie rolled off me and stood next to the bed. "I want you to eat my pussy, Ev," she said as she pushed her pants down to reveal white satin panties with a pink bow at the waist, a match to the bra that now lay on the floor. She sat on the edge of the bed, pulled off her boots, and finished removing her pants.

I got to my knees as she lay in the middle of the bed on her back. I put my dick back in my panties and crawled between her legs. My fingers rubbed the top of her pussy gently through the satin, and I leaned forward. I pulled the gusset to the side, and planted a kiss on her neatly shaved mound. Then my tongue snaked slowly up her slit, and I tasted the moisture in her cunt.

I hadn't gone down on a girl since my last girlfriend at the end of my Freshman year, three years ago. I was nervous at first, and my licking reflected that. My tongue was tentative as it ran up Jessie's pussy, and I paused between strokes, not really getting a rhythm going. But then Jessie took control.

"Put your tongue on my clit, Ev," she said, and I did. She gave a gasp and pushed her hips up to meet my mouth.

"Stick your finger in me." When I did, she gave a long sigh and arched her back, allowing my finger to get deeper in her cunt. I crooked my finger, pressing against the top of her insides, and she cried out, "Oh yes, Ev, right there." She hooked her fingers in the waistband of her panties and pulled them down to her knees. I grabbed them and took them the rest of the way off her legs, then put my head down to her pussy again.

I pressed my tongue to Jessie's clit and lost myself in the moment. I no longer felt anxious about eating her. All of a sudden it felt like I had been doing this forever. I pumped my finger in and out of her, occasionally curling it to press behind her clit. Soon Jessie was writhing and her hips bucked, and she yelled out, "Oh, I'm coming!"

My finger was suddenly drenched with her moisture, and even though her gyrations took her clit out from under my tongue I felt her pussy clench around my finger as she orgasmed. Her shaking slowly subsided, and I let my finger slide out of her cunt. I planted a kiss on the scant pubic hair above her crotch and looked up at her. She was smiling down at me.

"Evelyn," she said, "that was fantastic. Do you eat out girls a lot? You must have a lot of practice."

I blushed a little. "No, actually this is the first time I've been with a girl in three years."

"Well I couldn't tell," she said, propping herself up on her elbows. "That was the best orgasm I've had in a long time."

I grinned, and moved up so I could kiss her. I took the finger that had been in her cunt and licked up one side of it, tasting her pussy juices all over again. Then I held it to her mouth and she took the finger between her lips and slurped it clean, her eyes closed in pleasure.

When Jessie opened her eyes again, she looked right into mine. "I hope you're not too tired, Ev," she said. "I've got something else I want you to do."

"Oh?" I asked. "What is it?"

"I want you to fuck me."

"Okay." To be honest, I had been so absorbed my eating Jessie's pussy that I had forgotten all about my satisfaction. Now that she brought it back to my attention, I could feel my cock straining at my panties, yearning to get out.

I kicked off my heels and pulled down my tights and panties. Then Jessie helped me unbutton and remove my blouse. When I was sitting in just my bra I became self conscious. I didn't want to take my breast forms off, but if I took off my bra they might slip off on their own. Jessie saw me hesitate.

"Come on, Ev," she said. "You've seen all of me, now I want to see all of you."

I explained my dilemma. "So what?" she said. "Take the things off. I told you I want to see all of you, and that means I want you totally naked."

So I turned away from Jessie and reached behind my back to unclasp my bra. I dropped it off the side of the bed, then pried my fingers underneath the breast forms and took them off. When they were on the floor as well, I turned back to Jessie with my arms across my chest.

"Put your arms down, Ev," she commanded. I dropped them to my sides, and I felt her eyes rove over my body. "You're so pretty, Ev," she said finally. "Your body is almost boyish." She giggled at her inadvertent pun. "Oh, right."

I giggled at that, and we leaned toward each other and hugged. She kissed me, then pushed me away. "You know, I was going to have you fuck my pussy, but I think I want something else, instead." She got on her hands and knees and faced away from me. "Lick my asshole, Ev."

I turned to face her butt and put my hands on her cheeks. I pulled them apart slightly, just enough to bring the brown hole in sight. I moved my head closer, totally under her spell, and caught a whiff of the rank odor of her ass. I stuck my tongue out and licked it feeling Jessie shudder beneath my hands, but for my part the taste was off-putting. It was musky and bitter, and reminded me too much of the bathrooms at boys' summer camp when I was young. But I continued licking, spurred on by her groans and the way her hips gyrated in pleasure. I felt the tight muscle loosen under my tongue, and after a few moments I was able to drive the point of inside her ass. When I did that Jessie let out a yelp of pleasure and pushed her ass back into my face.

I made a hard point of my tongue and drove it in and out. I was getting used to the smell and taste, and it didn't seem so bad any more. I took one hand off her ass and reached beneath to touch her pussy. As I continued licking, I rubbed her mound, eliciting more and louder groans from Jessie.

I lost track of time as I rimmed her ass and rubbed her pussy, but eventually Jessie pulled away from me. "I want you to fuck me now," she said. "Put your cock inside me, Evelyn."

I got to my knees behind her and spread her cheeks again. Her ass was too high for my cock, so I reached my hands between her legs and pushed them apart until her hole lined up with my dick. I pressed the head against the brown ring and felt her tense up. I rubbed my dick head against it, dribbling saliva down the crack to lubricate her. I pushed as she relaxed, and before long the head popped in.

"Ouch," said Jessie. "Don't move, just wait a minute." I stayed still with the head of my cock in her asshole, feeling her clench and unclench her sphincter as she got used to having me in her. "Okay," she finally said, relaxing. "You can push it the rest of the way in."

I slowly slid my little dick in her tight ass, feeling it grip my shaft like a soft rubber ring. When I was all the way in, her soft ass wriggled against my hairless crotch. "Mmm," she moaned. "More, Ev." I pulled out until only my head was left in her, then thrust my hips forward. I found a rhythm and she matched it, pushing her ass back onto me as I pushed forward. It was incredible. Even as a male I had never fucked anyone up the ass, and I found I liked it.

All too soon, though, I felt my cum rising from my balls. I grunted, then squealed as my orgasm burst out of me. I felt like I hadn't cum in months. My dick pulsed over and over until I was drained. I pressed myself against Jessie's ass and held myself there, waiting to come down from the rush.

I pulled out and saw my seed leaking out of her and dripping down her leg. "Evelyn," she said sternly, turning her head to look at me over her shoulder. "You came too soon. I still need another orgasm."

"Oh, I'm sorry Jessie," I said embarrassed.

"That's okay, Hun. I'll get there soon." She wagged her ass at me as she looked me in the eyes. "Lick your cum out of me."

The sight of my jism running down her leg excited me, but thinking about licking it up off her excited me more. I eagerly put my head down at the level of her ass and stuck out my tongue. I licked her brown rosebud first, tasting the mixture of my cum and her musky, bitter rectum. My tongue slid inside her easily, and I slurped up as much of my cum as I could before I had to come up for air. The runnels had reached the inside of her knee at that point, so I directed my attention to that. The taste was the same, but not as intense. Salt, musk, and just a little bit of sweetness. I cleaned up her leg and returned to her asshole, sticking my tongue inside her again.

Jessie was moaning loudly by now. I knew her orgasm was close, so I didn't stop my licking. reached under her to rub her pussy and pushed my tongue in and out of her ass. Soon she clenched the muscle, trapping my tongue for an instant as she came. Her body heaved a few times, and she let out a high pitched keening that went on for a full minute. As she relaxed, I pulled my mouth away, and Jessie's entire body went limp. She collapsed onto her stomach, her face pressed into the sheets, and she lay there panting.

I moved my body up alongside her and put my arm around her shoulders. I smoothed back her hair and planted a kiss on her temple. She turned her head to me and smiled. I returned the smile, and we both rolled onto our sides facing each other. Our arms wrapped around each other's bodies and we shared a long, slow kiss. I snuggled closer to her as she reached down to pull up the sheets. I was already asleep, safe in her arms, when she turned out the lights.