Caren with a C

"Caren, you know me. I get it. I'm not going to tell you I won't be sad when you decide its over, but I get it."

"Next thing." she said. "I decide the pace. We are going to work up to the main event."

"Fine with me. I have no idea what I'm doing anyway. Obviously." I said, and Caren laughed.

"Also, we are both going the clinic to get tested."

"Uh, OK, but why? I'm a virgin"

"Because it is a good habit for you to get into as a sexually active adult, and you don't know where I've been."

"Are you worried about anything?" I asked.

"No, I was tested after I broke up with my last boyfriend and I haven't slept with anyone since then."

The implications took a minute to sink in. But then I asked, "So what's the problem?"

Caren sighed. "Look Tom, for me to feel good about this I want to make sure you learn a few things. Protecting yourself is one of them."

"OK," I agreed, "that makes sense."

"Finally, we are going to have to figure out what to tell your sister. I like her and I don't want her to think we are sneaking around behind her back."

"Probably easiest if you tell her we are dating or whatever, it would be awkward for me. Anyway, after I explain to her how Drake bailed me out tonight she will probably be all over him." It was much easier to accept after learning he had not slept with Caren. "I've been a little uptight about them maybe getting together but I guess it's good if we both lose our virginity before we go to college. He's a good guy. She could do a lot worse."

Caren laughed. "Shannon's not a virgin, you didn't know?"

I sat there with my mouth open. Shannon, sweet little Shannon, not a virgin? What the fuck else was I going to learn tonight.

Caren laughed again. "You are so gullible Tom. I don't know for sure but I think she is, like you. But frankly, that's none of your business unless she chooses to share it with you. Mine either. And I agree she could do a lot worse than Drake."

We got out of the car and I followed her upstairs to her apartment. I called home and told my dad I was going to crash at my friend Matt's house. Even though I woke him up he didn't bat an eye. Get good grades and your parents will cut you a lot of slack.

"All right," Caren said as she faced me in her small living room, "we are going to take this one step at a time."

Then she took a half step forward, closing the distance between us, tilted her head up and wrapped her left hand around the back of my head, pulling my lips to hers. They were warm and sweet and soft. I could feel her tongue running back and forth across my lips, gently probing them. I opened my lips in response and she slid her tongue in, opening them wider and gently exploring my mouth in a mind-blowing kiss.

When she came up for air she said, "Tonight, you get an anatomy lesson. Let's take off all our clothes."

She then began casually undressing, as though she was getting in the shower with no one else in the apartment. Sandals unstrapped and kicked off. Shirt over her head, revealing a plain white cotton bra I could see her nipples poking though. Shorts down around her ankles and off, leaving matching white cotton panties. Hands behind her back unfastening the bra and dropping it, allowing what I would later learn were C cup breasts to swing free. They sloped ever so gently away from her chest with the nipples pointing slightly left and right of dead center. They were unbelievable. Panties were unceremoniously pulled down, leaving a neat triangle of blonde pubic hair pointing down between her legs. Caren was lightly tan with faint bikini lines on her chest and pelvis. She had great hips and a stomach with a hint of a curve. I was fucking mesmerized.

"Now you." she said. "I'll help." Off came my shoes, socks and tee shirt. She knelt in front of me and unzipped my jeans, pulling them down and allowing my cock to strain against the tighty whiteys I was wearing. She pulled those down too, exposing my dick to the gaze of a woman I wasn't related to for the first time ever. Like many other things about my physical appearance, I think it's about average at a hair over six inches fully erect, which it absolutely was at that point.

"Sit down on the rug," Caren said, "with your legs spread out to the side." I did as I was told and then she sat down in front of me with her vagina about a foot away from my aching balls and her legs spread over mine. My rock-hard member sticking up between us.

"Have you ever felt a woman's naked breasts before Tom?"

I shook my head no, staring at them. Caren grabbed both my hands by the wrists and brought them up slowly, placing them gently on her gorgeous boobs. They felt amazing. Soft and warm and full, with her hard nipples poking into each of my palms. Instinctively, I pulled my hands back a bit and grabbed each nipple between my thumb and forefinger, rolling them back and forth lightly. Caren sucked in her breath and smiled, closing her eyes and obviously enjoying the sensation. Holy shit, I was pleasing a woman physically. It was the most incredibly erotic thing I had ever felt. The nipple massage went on for a minute or two, until Caren took my hands off her breasts and put them on her naked thighs.

"Next lesson. This is my vagina." she said, reaching down with one hand and spreading the lips apart with her fingers. "Take a close look." I looked down and saw her pink, glistening inner lips and darker outer lips looking back at me invitingly. "This is my clitoris." she said, tapping a small whitish button at the top where the lips all came together. "It's where the nerve endings that make me orgasm mostly are. Give me your finger."

I stuck out my right index finger and she pulled me in, turning my hand over and placing the pad of my finger on her clit. "Now, rub in circles, I'll guide you." I started rubbing in small slow circles and heard Caren's sharp intake of breath. She had complete control of my hand at first, but as I mastered the rhythm she let go and put both hands on the floor behind her, raising her hips up and towards me as I instinctively picked up the pace. It felt amazing. It was wet and slippery and rubbery and smelled unlike anything I had ever smelled before. I then understood the age-old comparison to tuna, but it was like comparing little league to major league baseball. They are sort of similar but wildly different and one is way better than the other.

"Oh, oh, oh, that feels good." She moaned.

I kept rubbing, continuing to increase the speed and eventually going as fast as I could. "Keep doing exactly that until I come." Caren said, as if she was telling me to how scratch an itch on her back.

She began moving her hips up and down in small motions and breathing faster and faster. I kept going for a few minutes, wondering what was going to happen next. Her legs started to tremble and shake over mine and she clamped her thighs together over my hand and let out what sounded like a long, low groan.

After about 30 seconds her legs relaxed and fell back apart and she opened her eyes and smiled. "That was fantastic. Best orgasm I have had in a long time. Your turn."

Without further comment she reached out and grabbed my cock, wrapping her hand around it gently and giving it a soft stroke from top to bottom and back up again. I was so turned on by the experience with her nipples and then fingering a woman for the first time that I immediately came. Huge pressure had been building in my balls and with the total lack of warning to Caren, it went everywhere. The first jet shot directly up in the air and came right back down on her hand and my dick. In her surprise, she reflexively pulled her hand towards her and the second blast of cum went all over her tan belly and the top of her pubic hair. She started laughing and got her other hand over the top to deflect the diminishing but still voluminous next few spurts.

"Wow, Tom. I guess I must really turn you on." Caren said with a reassuring tone in her voice.

I was completely mortified. "I'm sorry," I stammered, "I just... I couldn't..."

"Don't worry about it. I should have started with you first but I got so wet and horny once you began touching me I got carried away. That's also one reason we are going to work up to things. You are going to be experiencing some new sensations which will take a little getting used to and helping you through that process is a huge turn on for me. Now, let's get cleaned up and get in bed."

Caren stood up and walked into the bathroom of the decent sized one-bedroom apartment. I heard the water in the sink turn on and then splash as she ran something under it. Then her blonde head poked out from the door and said, "Do you want to come in here and get cleaned up or are you going to keep admiring the mess you made?"

I stood up and walked over the bathroom. Caren was standing in front of the sink running a wet washcloth over her lower stomach and vagina. She ran it under the sink again, squeezed it out, and then turned to me. The warm, soft cloth felt great as she gently cleaned my dick and balls, thighs and stomach. When she was done she kissed me deeply, hung the cloth over the edge of the sink to dry, took my hand and led me to her bedroom.

There was a queen-sized bed against one wall, taking up most of the room. It was neatly made with a light blue sheet folded back over a tan comforter. The pillow cases on the three pillows matched the sheet. Caren pulled back the covers on the right side of the bed and got in. The view I got of her naked brown body against the sheets as she slid her legs under the covers was unbelievably hot. She patted the left side of the bed and I moved over to it. The cool night air was blowing in though the open windows of the bedroom, covered by wooden horizontal blinds, which faced the back of the building and looked across a small open field bounded by woods. The crickets and other sounds of nature floated gently up from below.

I got in bed next to Caren, lying on my back. She rolled over and put her arm across my chest with her face next to mine. I could feel her soft breast pressing into my side. She ran her hand across my chest and down over my belly, ending up on my rapidly stiffening cock. Caren nuzzled her face into my left shoulder as she slowly stroked me to fully erect. She pulled the covers back then so I was lying naked next to her. Her soft hand moved up and down, pausing every few strokes to run her thumb over the head of my penis to spread the rapidly emerging precum around in a sensuous circle. After a few minutes my back began to arch and my breathing got quicker.

"Tell me when you are going to cum Tom." Caren said. "Give me a little warning."

"Oh god, Caren. Soon. I'm going to cum soon."

Caren leaned over and put the tip of my dick in her mouth while continuing to stroke my shaft up and down with her left hand. Feeling her mouth on my penis immediately sent me completely over the edge and I involuntarily thrust my hips upward as I shot what felt like a huge blast of semen into her mouth. Several more followed as she continued to gently stroke me with her hand, her lips keeping a tight seal around the head of my cock. When the spasms subsided she pulled back, swallowed and smiled.

"That was nice." She said.

"Wow, Caren. Oh my god. That was the first blow job I have ever had. It was amazing."

She laughed her wonderful laugh. "That wasn't a blow job Tom, not even close. You'll see. I was only trying to keep you from making another mess."

"Caren, I... I want to return the favor. Would you like me to rub you again, or lick you?"

"Yes, but not tonight. Let's go to sleep. It's late and I'm tired." I laid back and she put her head on my chest, one of her breasts lying on my chest and the other pressed up against my side. I fell asleep almost immediately.

I woke up the next morning in the most amazing way. The sun was up and streaming through the partially closed blinds onto to floor of Caren's apartment. I could see the dust motes floating through the still air though those shafts of light as I listened to her soft breathing. We were both still naked. In the night we had shifted positions and I was now spooning her from behind, my right arm draped over her as she lay on her left side. I could have held her like that forever. My rapidly inflating cock agreed and I moved over and rolled onto my back so it would not press up against Caren's naked ass while she was asleep.

Caren stirred and rolled towards me. She stretched and yawned and then a hand moved down over my torso to caress a now fully erect penis. "Good morning lover boy," she said, smiling. "Looks like someone is up for a little more action."

The sunlight was streaming in through the slits in the blinds. The temperature was perfect for an early summer morning, a little bit warm with the promise of heat to come, but with a light breeze to cool off the air coming in through the open windows.

"Tom," she said in a serious voice, "I was going to wait and find the right time for you to lose your virginity, but I think it might be now."

"Yes Caren, I want that very much."

Without another word she turned to her left and opened a drawer on her night stand, then turned back to me with a foil wrapped condom. She held it between us and said, "We are going to use this for two reasons. The first is, you always should unless you are in a monogamous relationship where both partners have been tested. The other is that first times are important Tom. I want you to have the first time you have sex without a condom as another experience to look forward to."

She ripped open the condom package and rolled the contents over my penis. That experience alone felt so intimate and erotic that I nearly came.

Caren leaned over and gave me a full kiss on the kips and then threw her left leg up and over my thighs so she was straddling me, with her pussy spread over the base of my cock. She moved slowly up, trailing her wet lips across the now plastic covered shaft until she was past the tip. Then she sat up on her knees and took my dick in her hand, positioning it under her body. She looked down. "Are you ready to experience this with me?" She asked. Her whole body was covered in goose bumps. She was definitely getting off on this.

"Yes, please let me be inside you."

She got the head of my cock lined up with her wet pussy, took a deep breath, and sank all the way down on me in one smooth motion. Her warm, wet, tight vagina surrounded my cock. The weight of her body rested on my hips. The soft, smooth skin of her waist was under my hands. Her majestic, tanned body rose over me, full breasts and erect nipples illuminated by small strips of sunlight beaming in from the partially closed blinds. Her green eyes looked deeply into mine. It was a great way to lose my virginity.

Caren let me savor the sensations, rotating her hips slowly back and forth so I could enjoy the experience without risking having me cum too quickly.

After a minute or two I began to move my hips upward every time she rolled her hips forward, creating a nice friction between my pelvis and hers, right where I now knew her clit was. We gradually picked up speed and she leaned forward and put her hands on my shoulders. "Oh god, Tom." She moaned. "That feels great. Just like that."

I kept up the steady rhythm for a few more minutes, spurred on by the fact she was obviously getting more and more excited and feeling somewhat amazed I could last so long, but I guess the condom helped. Caren went rigid on top of me, then groaned "I'm coming." in a low voice. I felt her vagina begin to contract rhythmically around me, triggering a massive ejaculation into the tip of the condom, followed by several more.

Caren collapsed forward on top of me, breasts mashing against my chest as she buried her face in my shoulder. After lying there for a minute she pushed herself back up onto her knees and then rose up so my deflating, condom covered cock slid out of her pussy and flopped onto my stomach. Caren got off the bed and stood beside it, reaching down to roll the condom off me while being careful to keep the semen in the tip from spilling out. Almost as an afterthought she leaned down and took me all the way into her mouth, sucking gently as she slowly worked her lips back toward the tip and then off me again. She stood up, smiled at me, and walked off towards the bathroom holding the spent condom.

By the time we got cleaned up and dressed and had a cup of coffee in Caren's small kitchen it was almost 10 a.m. Caren looked at the clock and sighed, "I guess I should go open up the store." We walked down the stairs from her apartment which were on the side of the building. Caren was a little ahead of me as we got to the bottom of the stairs so she rounded the corner first.

"Hi, Caren." I heard a familiar voice say as I was turning the corner. "I came by to pick up my backpack when you opened because..." Shannon was sitting on the bench in front of the store and trailed off as she looked back and forth between us. Mouth opening in surprise.

"Tommy, Dad said you were sleeping over at Matt's." Shannon said, confused. "I wondered why the car was here, but I thought maybe Matt picked you up here?" She stopped talking as the light bulb went off and she figured out where I had, in fact, slept.

Caren handed me the keys. "Open up the store Tom, your sister and I need to take a little walk. We have some things to talk about."

***

Thank you to all the contributors to the Literotica Writer's Resources forum. I read many helpful and thoughtfully written essays. I really enjoyed the process of writing and editing this based on that guidance, including removing 12 instances of the word "really". Posting it for the world to see, even anonymously, is making me nervous, but I want your honest and constructive feedback. I am already at work exploring how Shannon and Drake's relationship evolves.