How I overcame my awkwardness part 3 [m/f] | 2016

After my year in the States I returned to Canada to attend a Canadian university in my home town. A few months later, I was recovering from a passionless date with Mandy's best friend, Marcy, who had been my high school crush. I was at the grocery store when I bumped into a very different girl from my school. Her name was Tamara. I didn't know her really well but I had kissed her, impulsively, at the last school dance before graduation. I was slightly drunk at the time.

The students from my high school were mostly from well-to-do families, evenly divided between Jewish and WASP. There was a modest contingent of working-class kids. The groups didn't mix much. Tamara was from the working-class group. Unlike most of the wealthier kids, and all my friends, Tamara smoked. She smoked Camels, which were rarely seen in Canada at that time. High-school-aged me thought that was cool and exotic. Her blonde hair was in a pixie cut and I've always had a thing for short hair. She was a funky dresser, coloured tights under very short skirts, chunky shoes before that was fashionable.

"Ben! I thought you were gone! Off to the states to run track!" Tamara seemed pleased to see me, so I guess she wasn't harbouring a grudge for kissing her without an invitation.

"I'm back. It didn't go entirely well. But it's really great to see you. I'm, uh, sorry for unexpectedly kissing you on the dance floor." She laughed. She got really cute dimples when she laughed. "So what are you doing?"

"I'm working at a clothing store and going to school part time. I want to get my real estate license." She sounded a bit self-deprecating about it.

"That's great! I bet you'll be really good at selling real estate. You'll make really good bank."

"Thank you! And I hope so, I'm not doing it because I love going to open houses." She laughed and punched my shoulder. Interesting! Definitely body contact, though a bit percussive. I laughed, too, and turned my body more towards her, then touched her shoulder.

"You know, Tamara, I wish I'd got to know you better in school. Now that we're of legal age, can I buy you a drink?"

She smiled coyly. Were we making a date or just having a hook-up? I wasn't sure, but either way was cool with me.

A few days later, after some overpriced ice cream drinks at a smoky bar, we went to her place. She had roommates and we could hear the TV in the living room so we retreated straight to her room. She had a pair of twin beds. "Two beds?" I asked. She shrugged and explained that they were hand-me-downs. And then she moved me out of the way and pushed the two beds together. She grinned at me, showing her dimples again. Damn, she was sexy. She was also on the far side of the two beds, but she threw herself down and bounced her way over to me. She kneeled on the edge of the bed and pulled my face down for a kiss. This one lasted much longer than our first kiss at the dance. We came up for air. "Now we're even," she said.

"Oh, I'm not so sure. I think you over-compensated. Let's try and even that out." And I kissed her again. Her hands were on my ass, pulling me on top of her. That felt like a great idea. Our teeth clicked as I shifted my weight. Her mouth distorted with a little laugh but then she relaxed again, pushing her tongue gently between my teeth as her hands stroked my hair. I had one hand underneath her, massaging her wonderful, shapely ass.

Our clothes mussed and hair tousled, we paused for breath again. I looked into her eyes. "What's the matter," she said, "have I got something on my face?"

"No, I'm just thinking how very cute you are. And very desirable. Um, do you know Marcy ______?" She nodded and knit her brow, confused. "I had a date with her recently and we ended up back at her place. But the chemistry just wasn't right so we didn't do anything."

"And? How's the chemistry here?" She looked worried.

"Our chemistry is amazing." I said that last word with emphasis.

Tamara was relieved. "Wow, Marcy is, like, gorgeous, and rich. So, why me and not her?"

I shrugged. "I like you both. When I kissed her, it was... nice. No sparks, though. When I kiss you, when I smell you, I want to rip your clothes off and fuck you silly."

"Oho! Well then..." Tamara pulled my shirt over my head and then she slid herself down the bed to my waist. She undid my belt and pulled off my pants and then my socks. Then she pulled off my briefs. I was now naked and she was fully clothed, which felt strange. Tamara worked her way back up my legs, leaving little kisses behind. She put one hand under each buttock and lowered her face. I felt her wet tongue on my scrotum. And then she gently sucked one of my testicles into her mouth. I gasped. Her tongue teased the underside of my scrotum. She looked up at my face and from her eyebrows I could see she was smiling through her mouthful. Then her lips were on my penis. Her tongue twanged over my frenulum. I gasped again, it was almost too much. I felt her teeth lightly strafe my glans and then she made some long wet strokes with her mouth. I was going to lose control.

I told her I was getting ahead of her and got her to sit up. I pulled off her top and then her bra. Her breasts were small but high and plump. One was bigger than the other. They were perfect. I kissed them both, stroked them both with my finger-tips, and then I echoed her use of teeth by nibbling her nipples. She made a little yipping noise. I switched to sucking them gently. Some girls don't react much to having their breasts stimulated, but Tamara sure did. She was crushing my head into her left breast as I suckled it. Her chest was getting flushed. I unzipped her skirt and pulled down her tights, and she squirmed out of them. I started to lower her tiny pink panties. She put a finger on my lips and said, "I need to put in my diaphragm."

She grabbed her purse and then stuck her nose out the bedroom door. She groaned. Apparently the bathroom was in use. "No peeking, now," she said, and without taking her eyes off me she got out her diaphragm, put a little gel on it, slid off her underwear, and then as I watched, she squatted and inserted the diaphragm. As she moved to the other side of the bed to grab a kleenex, I saw her beautifully rounded buttocks. She had amazing, perfect skin. With the back-lighting of the window I could see the finest peach-fuzz on her butt and thighs. I felt another surge of desire for her.

I sat on the edge of the bed and pulled her to me, kissing her tummy. I lowered my hand to her pubic area, feeling the coarseness of her pubic hair. I could feel the wetness and the heat. She pushed me back on the bed and then climbed on top of me. I was crosswise over both beds, and as we moved around getting things lined up, my butt ended up dropping slightly between the two mattresses. Suddenly our bodies aligned and she slipped deeply down onto me. She moaned. I was sitting up and she was straddling me. I kissed her mouth, then nibbled her neck, and then scrunched a little so I could suck on her breasts. I could feel her juices running down my scrotum. Her hands were tightly around the back of my neck, stroking my hair. We were in a groove—literally—and it felt great. I felt like I could last forever like this as our bodies moved in harmony. I looked up at Tamara. Her brow was furrowed and she was scowling in concentration. She saw me looking at her and grinned. There were those dimples again. I felt another surge of desire and suddenly I felt the pressure building. I wasn't going to last much longer after all.

After a few more seconds her chest was flushed and her movements were getting jerky. I didn't need to hold back any more. I looked at her to signal that I was going to cum but her eyes were closed. I touched her face. With her eyes still closed she opened her mouth and my finger went in. She bit down, hard. I yelped and spasmed right as I was cumming. My movement made the beds shift apart, my butt suddenly dropped farther between them and I slipped out of her. The last of my cum spurted messily on her thigh and tummy. She looked down in surprise and then tilted her head back and laughed, a deep throaty sound. She dipped her finger in my semen and touched it to her lips and then to mine. I kissed her fiercely and she opened her mouth for me, no biting this time. It took some maneuvering but I got myself out from between the two beds and then we rotated and lay on one of the beds, naked and sweating. We kissed one another and stroked each other's bodies. She put her hands on either side of my head and then kissed my nose. She made dimples. "I hope we're going to do this again," she said.

That was the beginning of a relationship that lasted for more than a year, the longest relationship I had until I met the young lady who would become my wife. I completely, totally, passionately love my wife, and I have no regrets about how things worked out. But when I think of Tamara, it's always a fond memory.