Shannon's Summer of Firsts

I snuggled up next to him, put my head on his chest, "You didn't expect to get a 5 in AP physics after your first class, did you?" He reached his left hand under me hugged me tight. It was nice. I'll always remember the hug. It was the best part of the experience.

We had sex a couple more times over the next several days. They got a little better but they were still the bumbling affairs of two people that didn't know what they were doing. A week after I lost my virginity, Ray left for some sort of summer tech program Carnegie had started offering for incoming freshman. His family moved away later that summer because his dad got transferred. We traded a few letters but I didn't see him again for 20 years. When I finally did I discovered first hand he had developed into an amazing lover.

****

So my first time had not been great. I didn't regret my decision to have sex with Ray, at all. He was a good guy and we had experienced something new together. But I did wonder what I was missing. I decided I would ask Caren about it.

I arrived at the store the next day at noon. Caren was there and we made intermittent small talk while I got the returned tapes rewound and put back on the shelves, alphabetized the racks and did the other chores around the store while Caren checked out customers. Things quieted down about 2, midafternoon in the store was usually the slowest time. Everything was organized and ready so there wasn't a lot to do around the store and customer traffic was light until people started getting off work around 4 or so. Normally Caren would leave for a few hours during this time of day, one person could easily handle things. I was behind the counter and had pulled out a book, which Caren was OK with when there was no one in the store. She came out of the office and was walking towards the front door but stopped and leaned on the counter with one arm.

"Shannon, do you want to talk more about me and Tommy?"

I looked up from my book. Caren had a serious look on her face. "I'm happy for him. He's on cloud nine." I paused and added, "He told me he lost his virginity to you."

"Does that bother you?"

"No. I guess you're his girlfriend now?"

Caren sighed. "Sort of. Things between us are only for the summer Shannon. We both agreed on that. I'm not sure how you would describe our relationship right now."

"Oh, OK." Another question popped out of my mouth that led to one of the most memorable experiences of my life. "Do you like it?"

"Like what? Being with your brother? Yes, I do."

"No, I meant sex. Do you like it? I've never talked about sex seriously with anyone, about how it feels I mean. I know boys like it a lot, but what about girls?"

"The answer is definitely yes to both questions. But a lot of women need to learn how to enjoy their bodies, boys don't. It's hard wired into them."

"How does a girl learn?"

"Some explore on their own. Some have someone teach them."

"How did you learn?"

"I had a friend in college who showed me how to masturbate. Actually, it was more like she taught me it was OK to masturbate. Once I got comfortable with that I could tell guys what I liked and didn't like and that made sex much more enjoyable."

"How did she do that?"

Caren looked at me without saying anything for a minute. I could tell she was trying to decide what to say next. "Do you want me to teach you?"

"I think so. I'd like to at least try." I said nervously.

"OK, let's go up to my apartment."

"What, now?"

"Yup, no time like the present."

Caren took my hand and gently led me toward the front door. She turned the sign hanging behind the glass to 'Closed', locked it and led me around the corner and up the stairs. Her apartment was one of two above the video shop and faced the back of the building. She unlocked the door and guided me into her small living room, shutting the door behind us.

My heart was beating rapidly. I wasn't at all sure where this was going, but I trusted Caren so while I was nervous, I wasn't scared.

Caren put both her hands on my shoulders and looked me in the eyes. "What my friend did for me is have us masturbate together. Watching her get herself off helped me learn a lot about how to make myself feel good and that it was OK to do that. I'm offering to do the same for you now. What happens next is totally up to you. If you want me to help you no one but you and I will ever know. If you don't want to, that's fine too. Or if you want to think about it. We can go back downstairs and I won't say anything about it unless you bring it up."

I liked Caren. I trusted her. But I wasn't sure about this. "Would that make us lesbians?" I asked.

"No. We won't be touching each other. But even if we did it wouldn't mean we were lesbians. I've slept with a woman before Shannon, but I don't consider myself gay, just open-minded."

"What about Tommy?"

"What about him, I won't tell him if you don't."

"Wouldn't this be, like, cheating on him."

Caren laughed. "Oh, Shannon. You don't know men well enough yet. I am 100% certain Tom would not have a problem with this if you did tell him."

"Can I think about it?"

"Of course you can. The last thing I want is to pressure you into anything. Let's go." Caren turned and headed for the door.

As she opened it and looked back she saw I hadn't moved. She walked back to me and took my hands in hers. "Shannon," she said softly "I'm sorry if I freaked you out. I wanted to help you the way my friend helped me and I didn't think about how you might react to an offer like that. Let's go back downstairs. Come on."

"It's not that Caren."

"What is it then? Talk to me." She smiled.

"I want to try, you know, what you suggested."

"Are you sure?"

"Yes, I'm positive. But if I don't like it can we stop?"

"If there is anything that makes you feel uncomfortable I want you to tell me right away."

I looked at her. "So, what do we do now."

"Sit down on the carpet, like this, facing me." Caren pushed the small coffee table out of the way with her foot and sat down cross legged on the soft grey area rug. I sat down across from her, our knees a few inches apart.

"Close your eyes and take 10 deep breaths."

I followed her instructions and could feel my heart slow down to a more normal rhythm.

"OK. Open your eyes. I want to ask you a few questions. Have you ever masturbated before?"

I nodded yes

"So you're familiar with the different parts of your body, like your clitoris?"

I nodded.

"Have you ever had an orgasm?"

"I don't think so."

"You should definitely know if you have had one, so the answer is probably no. Are you ready to have your first?"

I nodded.

"Close your eyes again and take 20 deep breaths."

This time I heard Caren stand up and move around while I my eyes were shut and I felt her sit back down as I was finishing. When I opened them Caren was sitting in front of me, legs spread to either side of mine, knees slightly bent, naked from the waist down. Her hands were resting on her tan, fit thighs and I could see faint bikini lines on her hips coming together in a triangle of short, blonde pubic hair.

She leaned forward and took my hands in hers. "Do you still want to do this?" I nodded one more time, I could feel a warm, moist sensation beginning between my own legs.

"What works best for me if I want to get to orgasm is rubbing my clit directly." She took her right hand off her thigh and reached between her legs extending her middle finger slightly. I saw her reach all the way down to the bottom of her vagina and slowly run her finger back up towards the top, finishing by rubbing in a small circle. She did this several times, explaining she liked to get some of her natural lubrication onto her clit before focusing on it to enhance the sensation. Caren began to rub her hand back and forth, quickly picking up speed. Her eyes were closed and she moved her left hand to the floor behind her for support as she bent her knees more and spread her legs open wider.

I watched, fascination combining with a sense of unreality. It was almost as though I were watching this through someone else's eyes. Caren's hand was now moving back and forth rapidly. She opened her eyes. "You have to find the right speed and pressure, it's easy with a little practice. This is what works for me." She closed her eyes again, her hand maintaining a steady pace. "Oh god, this is such a turn on." Caren moaned softly. "I'm going to cum now." Her hips started to make small bucking motions as she continued to rub her clit and she let out a soft grunt with each one until her hand slowed and her body settled back onto the rug. "God, that was fantastic. What did you think Shannon? Do you want to try?"

Yes, I did. I stood up and stepped out of my shorts, standing in front of Caren in my tee shirt and yellow and pink striped panties, which had a large wet spot on the front. I hesitated, looking at Caren. Her face was at the same height as my crotch. She leaned forward and for a moment I thought she was going to kiss me there. I remember thinking it would probably feel nice. Instead, she reached out with both hands and put her thumbs under the waistband of my panties, slowly pulling them down past my knees and letting them fall around my ankles. "You have a beautiful vagina. I see you keep it bare. I like to do that sometimes."

Caren took my hand and pulled me back down to a sitting position. She was sitting cross legged again and gently moved my legs to either side of her knees, reversing the position we were in when she was touching herself.

"OK Shannon, start by doing what I did and let it flow into whatever feels the best."

I closed my eyes, reached down between my spread legs and ran a finger up my wet slit, pausing at the top to rub a few slow circles around my clit. It felt nice. I closed my eyes and repeated the motion a few more times, taking a little more time at the end with each pass. I could feel myself getting wetter and a warm, tingling sensation began to build, radiating out from my vagina. I focused exclusively on my clit, rubbing back and forth the way I had seen Caren do. I opened my eyes and found I was looking directly into Caren's face. Her green eyes were open wide and she was looking down at me touching myself.

"Keep going Shannon. Bring yourself over the top. I'm right here to help you though your first orgasm." She reached out and put her hands gently on my thighs. "Is that OK?"

I nodded yes and closed my eyes again, continuing to rub back and forth as the pleasure continued to build. I continued for what felt like a long time, with Caren murmuring soft words of encouragement, her hands slowly rubbing my thighs. I would build towards what felt like an impending crescendo only to start coming back down. After several cycles I stopped with my hand and opened my eyes again. Maybe that was an orgasm? I didn't know. It didn't seem like what Caren had experienced.

"I don't know Caren. I feel like I'm getting close to something but then it slows down again. It happened a few times."

"The first one is the hardest, at least it was for me, because you don't know what you are aiming for and how good it's going to feel. I have an idea, but it will mean me touching you. Is that OK?"

Since I was already sitting in front of her, naked from the waist down and masturbating, I didn't see a reason not to take it a little further. I wanted to see what an orgasm was like. "Yes. I trust you."

Caren extended her finger and reached down, placing it on the entrance to my vagina. "Relax Shannon, tell me if this is uncomfortable." Caren looked at my face as she slowly inserted her finger into my sopping wet hole. I gasped a little as she got to the first knuckle and then the second. I didn't hurt at all. It felt nice. She slid her finger in and out of me a few times. She pushed it all the way in a final time, paused and pulled it almost all the way out until only the tip was still inside me.

"Now I want you to start rubbing your clit again. When you feel yourself rising towards a peak tell me and I'll slide my finger all the way into you. Hopefully the extra sensation will trigger an orgasm."

I started rubbing myself again, picking up where I had left off. The warm waves of pleasure rolled up my body, becoming more and more intense. The tip of Caren's finger was moving gently up and down inside me, adding to the stimulation. But the climb leveled off and as before I could feel myself slowly starting to back away from the climax I so desperately wanted to achieve. "Now Caren." I practically pleaded. "Now."

Caren quickly slid her finger all the way inside me and lifted up slightly. For the briefest moment I didn't think anything would happen and then my slick pussy clamped down on her finger. It felt like a white flash went off in my head the pleasure was so intense. I felt myself loosen and contract again, even harder this time, the same explosion of sensation washing over me.

"Yes, oh God, yes Shannon, let it all go." Caren gasped out. "Keep cumming for me. That's it." Her finger stayed inside me with the same upward pressure on the top of my vaginal canal. My contractions continued, slowing and finally stopping.

Caren pulled her finger out of me and I collapsed backward onto the rug. Looking at the ceiling and breathing heavily. "Oh...my...god" was all I could manage.

"Amazing, right? I'm so glad I was here with you for the experience. That I could share it with you."

I tilted my head up off the rug and looked at her. "Thanks Caren. You're a great teacher." It occurred to me I was laying there with my legs spread wide open in front of another woman and it didn't bother me at all. It was turning me on.

I reached down and rubbed myself some more, slowly.

"Woah, I may have created a monster." Caren laughed. "But I suggest taking it easy, at least until tonight, to make sure all that new activity isn't going to make you a little sore. It might. Besides we have to get back down to the store before the afternoon crowd starts to show up."

We got dressed and went back down to the store. I wasn't sure what to think about everything that had happened. I alternated between a warm glow the orgasm seemed to have left and feeing weird about masturbating with another girl. Caren, meanwhile, went about her job as though nothing at all had happened between us. If she could do that, so could I.

About 8, as usual, Tommy rolled into the store. It was usually a busy time, but there didn't happen to be anyone else in the store. "Hi Shannon." "Hi Caren." He stood there a little awkwardly.

Caren smiled and walked over. She gave him a hug and a quick kiss on the lips. "Hi Tom."

I looked at him. "So is it Tom now, no more Tommy?" I asked, realizing finally Caren only used the more mature name.

"I hope I'm always Tommy to you Shannon. But I do like being called Tom. I think that's what I'll tell people to call me when I get to college."

It didn't take long for us to fall right back into our old friendly routine. Talking and joking. Making Tommy do stuff around the store even though he wasn't getting paid. Chatting with the regulars. The usual.

I looked up when the bell on the door tinkled and my mom came into the store. My parents rarely rented movies. They didn't watch many movies at all, and when they did they had a bunch of old classics at home. Apparently, it was impossible to watch 'Singing in the Rain' or 'Casablanca' too many times.

"Oh, hi Mrs. Norco. Good to see you." Shannon said cheerfully, walking over to her. 'I screwed your son and taught your daughter how to masturbate.' I added silently.

"Caren, I've told you before to call me Mary." She turned to me. "Your dad and I want to see..." She named some movie. I can't remember what it was.

"You could have called the store Mom."

"I know, since the two of you are always here, but I had to come right by here on my way home from the PTA meeting."

"I was hanging out with Shannon." Tommy said, a little too quickly.

"Here you go Mary, on the house." Caren handed her tape.

"That's not necessary Caren. Charge my account. And tell your parents I said hello."

"Sure, good to see you."

Mom left the store. I couldn't resist. "So Tommy, are you going to tell mom and dad you and Caren are, like, dating?"

Tommy looked like he was going to say something, but didn't and glanced hopelessly over at Caren.

She laughed. "Tell them whatever you want. Or don't. But Shannon," she looked at me "that's Tommy's decision to make, right. Neither of us will say anything?"

"Of course not, I'm teasing."

About 9, Drake came in. he was wearing a Red Sox tee shirt, jeans and a pair of beat up high top sneakers. He looked fantastic. "Hi guys. How ya doing."

We all answered with some version of 'Good' and got quiet. Each thinking different thoughts. He looked around at us, suddenly aware there was a weird vibe. "OK, what did I miss? Is something wrong." He got serious suddenly. Sometimes customers could say inappropriate things and he was protective of me and Caren.

I looked at Tommy. He looked at me and at Caren. Then he turned to Drake. "Caren and I are sort of dating."

Drake could have said a lot of things. It would have been easy to tease an obviously awkward Tommy. If Tommy had been one of his buddies I'm sure he would have, I could tell he sensed that was the wrong move. "Cool, I'm happy for you guys."

"Drake, how about taking me for a ride on your motorcycle. We can give the two lovebirds a little time alone. In fact, you can take me home and we will make up an excuse about the car needing to be fixed so Tommy can get home later than usual."

Tommy looked profoundly grateful and glanced over at Caren with a smile. I hoped he wouldn't get a boner and embarrass us all.

Drake looked surprised and amazed. Like he had received an awesome birthday present. Then he settled back into a more cautious demeanor. "Sure Shannon, it's a beautiful night. I don't have the bike, but I've got a great old convertible mustang I've been working on. I'm test driving it. Let's go."

Caren winked at me as we walked out.

I didn't know much about cars, but I loved the old Mustang as soon as I saw it. The lights from the store were reflecting in the red paint and thin chrome front bumper. The windshield was slightly swept back and I had the impression the car was moving, even parked in the lot. Drake walked next to me to the car, I could feel his presence and smell the faintest hint of aftershave or cologne. We walked up to the passenger side of the car and he reached past me to open the door. I settled into the slightly worn, but soft, black leather seat. Drake smiled as he looked down at me while shutting the door and I saw him sneak the briefest glance at my legs where my shorts had ridden up a bit. I shivered slightly and felt myself start to get wet.

Drake fired up the car. The radio blared out a song from the local rock station, much too loud. He reached out quickly and turned it off. "Sorry, it's a little hard to hear the radio with the top down. We don't need the radio anyway. Let's listen to the wind and the road. Where are we going?" I told him where I lived and he put the car in gear and turned to pull out of the parking lot.

He suddenly stopped and got out of the car. He went up to my VW and pulled some sort of tool out of his pocket. I heard air hiss and saw the right front tire go flat. He got back in the car.

"What did you do that for?"

"I don't like lying to people. Now I don't have to."

He put the car in gear again, made a right and accelerated. "These cars aren't about high performance even though that's how a lot of people think of them Shannon." He had to raise is voice a little as the wind noise increased. "It's about the look and feel and experience. Ford forgot about that. The new Mustangs are a travesty, but the older models are a thing of beauty." He looked over at me a little sheepishly. "Sorry, I don't want to bore you. I get a little carried away sometimes."