Jessica

I was a late bloomer, sexually. I never had any girlfriends in high school; in fact I was too painfully shy to even talk to girls. As a result, I was still a virgin in my second year of an honours biochemistry/physiology degree, at the age of 19, when I met the woman who would come to dominate my life.

Jessica was a 35 year-old grad student, doing a PhD in biochemistry. A statuesque woman with long auburn hair and green eyes, she was always slinking around the campus wearing something tight-fitting and sexy. It was obvious from her sleek, well-muscled body that she worked out regularly in the gym.

I'm only 5'9", and Jessica is over 6', so she seemed to tower over me. I'd been having wet dreams about Jessica since I'd first laid eyes on her. I knew she worked as a Teaching Assistant in the chem lab, so when I started second year, I deliberately signed up for one of her labs.

As usual, though, I was way too shy to strike up a conversation with her, or even ask questions about the lab assignments. Perhaps she was attracted by my shyness, though, because she took a special interest in me. She began to help me personally with my assignments, often staying after the lab to give me special tutoring. She would lean over, making sure I got a good view of her cleavage. Needless to say, I soon started getting top marks in biochemistry!

After a few of these after-class sessions, she invited me to join her for a drink in the campus pub. After a couple of pints, she began to ask personal questions, particularly whether or not I had a girlfriend. "I've never had a girlfriend," I blurted, "I'm still a virgin".

She greeted this assertion with a coy arching of a sculpted eyebrow. "Let's continue this discussion at my place," she said, so we finished our beer and left the pub. She took me by the hand as we walked out the door. Her apartment was just a short walk off campus, so the walk only took a few minutes.

She poured a couple of glasses of red wine, put on a Siouxsie and the Banshees CD and indicated that I was to sit beside her on the couch. She told me she enjoyed tutoring me in chemistry, and we drank a toast to my continuing good marks. Then she leaned over and kissed me full on the mouth. She wrapped her arms around my shoulders and slipped her tongue between my lips. Well, I'd never been French kissed before, the only kisses I'd ever had were a few chaste pecks on the cheek from my aunts and female cousins. I must admit I recoiled, my body stiffening in shock.

Jessica chuckled and said, "you've never been French kissed, have you, Chris?" Too embarrassed to speak, I just shook my head. "Well, do you want to continue, or have I embarrassed you too much?"

All I could do was nod enthusiastically, which she interpreted correctly as a signal to continue. She enveloped me in her arms and kissed me deeply, exploring the inside of my mouth with her tongue. She ran her hands down my body and rubbed my erect penis through the fabric of my jeans, then unzipped my fly and pulled out my penis. She traced the edge of my glans with her ruby-red fingernails, then began to gently stroke my member.

"Why don't you do a little strip-tease for me?" she asked, so I stood and made up a bump-and-grind routine while Siouxsie sang "Swimming Horses". I clumsily peeled off my clothes and danced naked in front of her, my engorged penis slapping against my belly.

She held out her arms to me, and I slipped naked into her embrace. I snuggled my head between her ample breasts while she gently massaged my penis. I was so aroused, it didn't take long before I came in a thunderous orgasm.

That was the end of our first evening together. Jessica said she had an early class the next day, so she needed her sleep.

"You'd better put your clothes on now, Chris, and I'll see you again in the next chem lab."

I cleaned myself up in her bathroom, she kissed me goodnight at the door, and I returned to my room in the student residence with my head spinning, filled with all sorts of wonderful fantasies. That night in my bed, I masturbated furiously while running the evening's events in my mind.

I didn't see Jessica for a couple of days, but there she was, as usual, in the chemistry lab on Friday afternoon. She gave me a wink and a sly smile as I sat down in my usual seat at the back of the class. I could hardly concentrate on the lab exercise, and I was afraid to stand up because everyone in the class would see the bulge in my pants.

After the class, I slowly packed my books into my backpack and waited for the other students to leave. Fortunately classes empty rapidly on Friday afternoons, as all the students are anxious to get to the bars.

Jessica came over and said, "why don't we skip the bar tonight, Chris, and just go straight to my place?"

I eagerly agreed to this proposal. When we got to her place, Jessica asked me to pour a couple of glasses of wine while she put on a Norah Jones CD. She sat on the couch and sipped her wine.

"Do your little dance for me again," she requested.

I gyrated and shed my clothes piece by piece while Norah sang. I danced naked in front of her until she said, "come here and drink your wine, Chris." I sat beside her and took a sip, then snuggled up against her warm body.

Jessica took me in her arms and we French kissed while she stroked my penis gently with her red-nailed fingers. She played with my testicles, then drew her fingernails lightly up the length of my penis and stroked my glans. She kissed me again while she gently pinched my nipples. She unbuttoned her blouse and released the front clasp on her bra, revealing her full, firm breasts. Her nipples had small barbells placed horizontally through them, and there was a butterfly tattooed just above her left nipple. Jessica pushed the nipple toward my mouth, indicating that I was to suck on it. I kissed her nipples and played with the little barbells with my tongue and lips, while Jessica moaned with pleasure.

Jessica slipped off her panties, hitched up her miniskirt and spread her legs.

"Kiss me on my vagina, Chris," she requested.

I slid to the floor between her legs and placed my face under her miniskirt. I'd seen naked women on stage at the peeler bars, and close-up pictures of vaginas in magazines and on the Internet, but I'd never been this close to a real, live pussy before!

A small ring with a bead peeked out between the lips of her hairless vagina and there was a tattoo of a hummingbird sipping nectar from a flower on her mons. My already stiff penis began to throb painfully. I had no idea what I was supposed to do, but Jessica patiently explained to me how to lick her and play with her clitoris with my lips and tongue. I traced the edges of her labia with my tongue and circled her clitoris. I tugged gently on the bead with my lips. Her clitoris was much larger than I expected a clitoris to be, standing fully two centimetres when erect.

After about 20 minutes of licking and kissing her vagina and sucking on her great big clitoris, Jessica began to moan softly and she rhythmically pushed her vagina against my mouth. Finally, she let out a long breath and shuddered slightly, then relaxed.

"Thank you, Chris," she said. "You brought me to orgasm. You're not very good at it yet, but you'll improve with tutoring". So now Jessica was not only my chem lab TA, but my sexual instructor as well!

After her orgasm Jessica held me in her arms and kissed me. She stroked my penis until I squirted thick milky sperm all over my belly. She scooped some up on her fingers and smeared it on my lips. I'd never tasted sperm before, but I licked it all off my lips. At first I didn't like the sickly sweet taste of it, but Jessica fed me some more. As I sucked on her fingers, I began to enjoy the taste of my sperm.

By this time it was midnight, and as she had an early squash game on Saturday, she had to get some sleep. She told me to put my clothes back on, but she kept my underwear and told me not to wear underwear any more. She said she'd call me Saturday afternoon, and I could come over to see her again. I spent much of the night frantically masturbating and fantasizing about Jessica. I thrust my penis in and out of my pillow, pretending it was Jessica, and fell asleep wondering when she would let me put my penis inside her beautiful vagina.

Some buddies called me the next morning and we went over to the rink to play a game of hockey. After the game, while we were having a beer at the pub, Jessica called me on my cell phone, so I told my buddies I had to leave. By this time, it was pretty obvious to all the guys in class that I had something going on with Jessica. My friend Will teased me about being "teacher's pet", but I just grinned suggestively.

"I'm getting what I deserve", I replied.

I ran over to Jessica's place as fast as I could, eager to learn what we would do next. I called her on the intercom, and the lobby door buzzed as she opened it for me. I went up the elevator, and knocked on her apartment door. Her eye appeared in the peephole to confirm that it was me, and the door opened.

"We'll skip the dancing today, you can just take your clothes off," she requested.

I quickly shed my clothes and stepped naked into her embrace. She probed my mouth with her tongue and rubbed the cheeks of my ass. She took me by the hand and led me to living room, where a glass of wine waited on the coffee table.

We kissed on the couch for a while and Jessica caressed my penis. "I've got a little surprise for you, today," she said. She reached into the drawer of the end table beside the couch and brought out a slim silvery vibrating dildo and a tube of KY Jelly. She told me to put my feet up on the armrest of the couch and spread my cheeks. Then she squeezed some lube onto her fingers and reached around beneath my buttocks. She massaged my sphincter and then slipped a finger into my anus and lubricated me with the KY. She worked her finger slowly in and around my rectum to relax the sphincter muscles, then turned on the vibrator and slid it into me. The buzzing of the vibrator against my prostate gland was the most incredible sensation I had ever experienced! I began to masturbate in time to her thrusts and soon I exploded in an incredible orgasm.

As before, she scooped up my sperm and fed it to me. I licked most of my sperm off her fingers, and then she handed me a Kleenex to wipe up the rest of it. She rubbed some KY Jelly on my penis and massaged me while we kissed. Pretty soon I was having another orgasm. By this time, I was all covered with sperm, lube and sweat so Jessica said she would have to give me a bath before we went out for dinner.

Jessica ran the water and poured in sweet-smelling bath oil and I slid into the hot, scented water. She lathered me all over with soap, massaged my penis and probed my anus with her finger. Then she told me to sit on the edge of the tub and open my legs. I wondered what was next when she got out a pair of scissors and a disposable razor from the drawer.

"I'm just going to give you a little trim," she said.

I must have looked rather hesitant, because she assured me, "don't worry, it grows back!"

She cut off all my pubic hair with the scissors and then lathered me with shaving cream. She carefully shaved away the stubble around my penis and testicles and then had me stand up and bend over while she shaved around my anus. She removed all my underarm hair in a similar manner, and rinsed me down with the hand-held showerhead. I'd never been shaved in these places before, so the result was not exactly pretty. She hadn't nicked me anywhere, but the tender skin looked rather an angry, red, scraped mess. She rubbed me down with moisturizing lotion and said that if I shaved regularly, the skin would get used to the treatment, the same way the skin of my face had when I began shaving. I'd learned by then that Jessica's "suggestions" were really orders, so I understood that I was to keep myself clean-shaven from then on.

After my bath, I put my clothes on, and Jessica took me out to dinner at a local Thai restaurant. Will, from the hockey game, was there having dinner with his girlfriend Candace, so I gave him a wink and a thumbs-up sign as we walked by on the way to our table. Jessica recognized him as one of her students, so she gave him a quick smile too.

Will just shook his head as if to say, "You lucky son-of-a-bitch!" If only Will knew what was really going on! After dinner, Jessica drove me back to the residence and gave me a long deep kiss before letting me out. She said she'd call me, and reminded me about shaving regularly.

I was so excited I could hardly stand to wait for her call. I rubbed myself almost raw masturbating. After class a couple of days later, there was a message in my voicemail saying she was cooking dinner for us, and I was to appear at her door at 6:00 p.m. sharp.

I had a quick shower, remembered what she'd said about shaving, and after shaving the wispy bits on my chin, I gave my pubic area and armpits a quick once over with the razor.

When she opened the door, Jessica was wearing a short black miniskirt and a sheer, see-through top and nylons with garters. It was quite obvious that she wasn't wearing any underwear.

I quickly disrobed and we kissed and hugged. I poured a couple of glasses of wine, and went to sit in the living room with her. "Let me inspect your shaving job," she said, and she ran her hands all over my penis and testicles. I'd done it in rather a hurry, so it was a bit bristly in places.

"You'll have to learn to do a better job than that!" she said, with a disapproving frown.

She ordered me to turn over and place myself across her knees. As I lay there with my erect penis pressed against her thighs, she delivered ten swift sharp smacks with her open palm to each of my upturned cheeks. I hadn't been spanked since my mother last did it to me when I was about five years old, so my face quickly flushed the same bright red colour as my ass cheeks. I was so humiliated, I began to sob and sniffle. However, I found the stinging, tingling sensation and the humiliation highly erotic and my penis began to throb even more that it had before.

Jessica took me to the bathroom, lathered me up as I stood in the bathtub and gave me a thorough depilation. I'm not the hairiest guy in the world, so it wasn't a lot of work. As well as shaving my pubic area and underarms, she removed the little wisps of hair around my nipples and shaved my legs. Then she rinsed me down, dried me off and massaged me with moisturizing lotion.

Afterwards, as I lay in her arms, Jessica rubbed some lotion into my sore buttocks and told me everything was OK, she still loved me, but I'd have to learn to follow her instructions precisely if I wanted to avoid similar treatment in the future. I sheepishly promised to do better.

It was a little bit uncomfortable sitting on my chastised buttocks at the dinner table, but the warm glow reminded me of Jessica's stern love for me. After dinner, I cleaned up the kitchen while Jessica sat in the living room with a glass of wine. I loaded the dishwasher and wiped off the counter, then joined her in the living room. Jessica gave me another lesson in how to please a woman, and introduced me to the pleasures of anilingus. At first I was reluctant to do as she instructed, but I quickly came to enjoy the musky scent of her anus as much as I did the sweet nectar of her vagina. As she lay back on the couch with her buttocks up on a cushion and her legs spread, I put my head under her miniskirt and licked and probed her vagina and anus with my tongue.

These evenings of ours quickly established a pattern. I'd disrobe, pour a couple of glasses of wine, we'd retire to the living room and I'd put on a CD. Sometimes I'd dance naked for her for a while, then slide into her loving embrace. Jessica likes mellow music, and mainly female vocalists, lots of Sarah McLachlan and Cowboy Junkies, but sometimes she likes something a bit more punkish so I'll put on some Kim Deal or Sonic Youth. Her favourite song is Sarah MacLachlan's "Possession". Many times I've laid naked in Jessica's arms listening to Sarah's haunting lyrics. "And I would be the one to hold you down, kiss you so hard, I'll take your breath away, and after I'd wipe away the tears, just close your eyes, dear."

Often, Jessica would introduce some new variation. After we'd been dating for a month, she greeted me at the door wearing a tight black leather outfit which exposed her breasts from the nipples up. A large black rubber strap-on was attached to her crotch by a set of straps and buckles. My eyes goggled at the size of the dildo, fully nine inches long and an inch and a half thick, but Jessica assured me that I'd be able to take it. She'd been using progressively larger dildos on me during our anal sex sessions, and my sphincter had been sufficiently stretched to handle it.

"I've been working you up to this one", she explained.

We sat on the couch and I sucked on Jessica's nipples while she squeezed some lubricant from a tube onto her finger. She had me lie across her lap while she lubricated my anus. She took a dildo from the drawer and worked it in and out of me, relaxing my sphincter muscles even more.

"Now lie across the armrest and spread your buttocks," she told me.

I did as requested, and Jessica slowly began to penetrate my anus with her rubber penis. She worked slowly at first, pressing in and backing off, going a little bit deeper each time. When the corona of the dildo slipped past the ring of my sphincter, she thrust it all the way into me. I gasped as the dildo suddenly filled me. The sensation of having Jessica inside me drove me wild and I began to masturbate.

Another time, after I disrobed in the hallway, I stepped around the corner to find a woman I didn't know sitting in the living room. Jessica introduced me to her squash partner, Victoria.

"We have no secrets from Victoria", she informed me, and told me to display myself to her friend. I turned a couple of pirouettes in front of Victoria to display my nakedness.

"Oh, I like that, Jessica", Victoria said. "May I?" She took my hand and pulled me towards her, so I sat on her lap. She began to inspect my penis and fondle my body. Victoria had close-cropped black hair and large dangling hoop earrings. Both ears were pierced several times, and a small stud pierced her nostril. She was wearing a leather jumpsuit with zippers in strategic locations. She unzipped the upper zippers, exposing her breasts, and pushed my head down towards them. Her nipples had large gold rings placed through them. I kissed her breasts, sucked on her nipples and played with the rings with my lips and tongue.

While I was sucking on Victoria's nipples, Jessica brought some leather cuffs and short lengths of chain out of the cupboard. She told me to sit on the couch, then she and Victoria placed the cuffs around my wrists and ankles, shackling me with my hands behind my back.

"Show Victoria what I've taught you about pleasing a woman," Jessica told me.

Victoria opened the lower zipper exposing her shaved vulva. Victoria was pierced there too, but she had five rings in each of the labia minora, as well as one through the clitoris hood. A small chain hung from the ring in her hood and laced its way through the other rings. A small padlock on the bottom end of the chain prevented it from being withdrawn, effectively sealing her vagina from penetration. I kneeled between Victoria's thighs and buried my face in her crotch, eagerly licking and sucking her womanhood and playing with her rings. Under Jessica's tutelage, I was getting better at this all the time and within 10 minutes, I had Victoria bucking her hips and moaning.

Jessica wiped up the excess juices that dribbled from Victoria's vagina and the sweat from her brow and kissed her on the lips. The two women held the kiss for a long time while I stared in fascination. This was another thing I'd only ever seen in pictures!