Life on the Edge of Orgasm Pt. 05

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My virginity lost, finally.
9.1k words
4.58
26.4k
28

Part 5 of the 5 part series

Updated 06/07/2023
Created 05/21/2015
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This is part five of a multi-part series. You are encouraged to read parts 1 - 4.

*****

Part 5

Chapter 28

When Stephanie came to pick me up Tuesday, she brought a pair of red panties. I looked them over, it looked like they might fit.

"C'mon, Stephanie, I'm not into cross-dressing," I told her, "I didn't know you were."

"Look at those, no lace, no nothing. They'll look like a sexy swimsuit. Put 'em on."

I stepped in and pulled them up. They might have passed for a swimsuit, but the fabric was flimsy and stretchy. They were much more revealing and didn't support me like a swimsuit would have; I flopped all over the place when I moved. Steph and Michelle thought it was great. In the right place - on the beach or at a pool - they might not be taken for panties. I shrugged; she'd originally wanted me nude for the drive to her house. She'd won a silly game against my sisters and claimed me for a night as her prize. Sounded good to me - I was looking forward to losing my virginity, but we hadn't made any ground rules and she wouldn't tell me what she had in mind.

Stephanie's parents had been divorced a long time and her mom was out of the picture. When she turned 18, she moved in with two friends, enabling her dad to take a job in Saudi Arabia for a couple of years, but he was still paying her bills and allowance. Her roommates were both college freshmen she'd known from childhood. That made Stephanie the only high school student we knew who had moved away from home.

Stephanie ushered me over her threshold into the living room; I was surprised to see six college-aged girls sitting there. Stephanie introduced them as her two roommates, Kristin and McKenzie, and four of their friends. Kristin and McKenzie weren't going out of town after all. They were both smiling at me like we already knew each other. I felt an immediate attraction for McKenzie, beautiful wavy brown hair falling across her face covering one eye, so she was continually pushing it out of the way. Something about that seems sexy to me. It was uncanny the way her eyes matched her hair perfectly. She was slender with a beautiful round butt. Kristin wore glasses and had her black hair cut short; she was so thin she might blow away in a stiff wind. There was a slight gap between her front teeth that gave her a distinctive appearance without making her less attractive.

Stephanie introduced me as her best friend's brother, telling them I'd lost a bet and was her "personal assistant." I laughed at that, but it was a pretty good story. The girls started urging her to take my swimsuit; I started to get excited. Stephanie led me into the middle of the room, and without warning, pulled my panties to the floor. The girls clapped and whooped it up a little. My cock started rising, drawing another round of cheers. Stephanie sent me to the kitchen to get wine for everyone. I found the kitchen and pulled a bottle out of the wine rack without looking at the label. After a brief search, I found wine glasses and a corkscrew.

The first two glasses went to Shelly and Chris. Shelly was short, and a little overweight, with small hands and eyes that closed every time she laughed. She was cute and full of energy; I never saw her stop smiling. She rubbed my ass and gave me a little swat as I walked away. Chris was pretty, with perfect skin, perfect make-up and perfect hair. I remember her hands, silky smooth with long fingers and a French manicure. Next I served Talia and Renee. Talia was looking at me excitedly, like she was really looking forward to the evening; I don't know what she expected. Her face showed a trace of Asian ancestry that I found captivating. Renee was the sexiest by far; not the prettiest, but her body language was all about sex.

Every time I entered the room, conversation stopped and seven sets of eyes watched me walk in. The first couple of times I was dangling and swinging. When I came in to serve McKenzie and Kristin, my erection led the way. Mac and Kris both gave my cock a little squeeze. After serving Stephanie, she sent me for snacks and another bottle of wine. I topped off the glasses and went to stand beside Stephanie. She was rubbing my ass with her right hand, occasionally squeezing my balls lightly. Conversation continued as if I wasn't there; they were talking about somebody I didn't know.

Shelly asked Stephanie to hand me over. Stephanie pushed, I walked over and stood in front of Shelly with my cock right in her face. She put her hands on me taking a good look at my cock from all angles, then guided me to her side, so she could play with my dick while she talked with her friends. She kept me there, rubbing me gently until the wine glasses needed refilling. Shelly handed me off to McKenzie, who picked up where Shelly left off. I noticed all the girls taking long glances at my dick as they talked, but Talia seemed to be focused on it. I was getting seriously turned on by her attention. McKenzie eventually passed me on over to Chris. None of them was really stroking seriously, but I felt an orgasm getting closer and closer. I wasn't planning on holding back. I tried not to let it show in my face; I wanted to surprise someone.

When I got to Talia, she stood me in front of her face and concentrated on what she was doing. What she lacked in experience she made up for in enthusiasm. She put both hands on me, tugging at my balls, stroking my cock. The other girls noticed Talia's efforts, and stopped talking to watch. She got into a rhythm, and kept it up until my cum hit her face. She was pretty unhappy with me, so I apologized for catching her off guard. She went to clean up in the bathroom.

Renee grabbed my arm and pulled me over to her, taking my cock in her mouth. She sucked until I was hard, and kept going for a while. I think everybody was surprised, if not shocked. I never expected to get a blow job in a room full of people, but I was not complaining. I was getting close to another orgasm when she stopped, gave me a wink and a nasty smile and sent me to Kristin, who asked me to open another bottle of wine first.

The ladies were getting tipsy, and a little more aggressive with their play. Stephanie told me not to cum again without asking first. I went around the room again, this time they each kept stroking until I warned them of an impending orgasm. Renee was so good, she kept me on the edge for a long time. The pattern continued until well past midnight.

Shelly finally announced it was time for her to go home, but she wanted to see me cum again before she left. I was happy to hear that; I was so damn horny I couldn't see straight.

Stephanie pushed the coffee table into the middle of the room, telling me, "Stand right there and cum for us. Be sure to get it on the table and not the carpet."

Jerking off for a room full of ladies is a favorite fantasy of mine, and always will be, no matter how many times it happens. It didn't take long this time. I looked around the room as I stroked, at all eyes watching me. When I looked toward Renee, she made eye contact and licked her lips seductively. I couldn't hold back any longer; I think my second orgasm might have produced more cum than the first. Shelly left, followed soon by the rest of the guests.

Mac waved me over to sit on the sofa with her, while Kris moved to sit on my other side. They both had a hand in my lap, occasionally petting or squeezing my cock as we talked. Their teasing had me fully erect again pretty soon. Before long, Stephanie stood and held out her hand, leading me into her bathroom for a shower. It was my first opportunity to inspect her entire body up close, so I took my time and covered every inch. Using my tongue, I developed an intimate knowledge of her nipples. Her ass was so smooth - I checked it with my tongue, it was smooth all over - to this day I wonder how women keep their asses so smooth.

Stephanie wasn't as experienced as I thought, but we both knew the basics and between us we figured it out. My cock finally found itself in the warm, wet, velvety place it was meant to be, and was in no hurry to leave. As a soccer player, I expected Steph's legs to be strong, but her upper body strength surprised and delighted me. And her legs; when she wanted me deep, she could wrap them around and pull me in tight. The next morning we woke up early but stayed in bed until noon, just generally enjoying each other every way we could think of. We agreed to put off any kind of relationship talk until school started; I intended to get into Denise's pants, and didn't want to feel guilty about it.

Chapter 29

I was on good terms with Denise when she left. I don't know why she didn't want to be my first, but she didn't mind being my second. I spent four nights with her; she was very passionate, but always in control of her passion. She taught me a lot, but most importantly, my mate's orgasm should be my top priority. I'll always get there, it's a foregone conclusion, so I should make sure she's happy; if she's happy, everybody's happy. Once Denise was gone, Michelle and I had the house to ourselves for two full weeks before school started. Mom was still in Beijing, and Morgan moved into her dorm early along with the rest of her volleyball team.

Michelle and I spent a good portion of each day naked together, and had a hard time keeping our hands off each other. As much as I wanted her in my bed, I was still waiting until I knew she was ready. We used our fingers and tongues on each other quite often. Michelle put something on whenever her friends came over, so they wouldn't feel uncomfortable or pressured. She never asked me to dress, so I didn't. Most days, she had at least one guest. I remember that two weeks as one long sex party.

Michelle scheduled her tennis team sleepover, and we discussed it beforehand. All the seniors were coming this time, including Gabriella and Samantha, both of whom missed the swim party. They would all sleep in the upstairs game room in sleeping bags or blankets or whatever they brought to put on the floor. I asked Michelle if there was anything in particular she wanted me to do. She wanted to play Denise's game.

"How about we do it without the tying down part?" I asked.

"That's my favorite part," she replied. "Please?"

Pretty girls seemed to have some kind of power over me, I just can't resist. She asked if there was anything I wanted to do. I didn't want to tell her I was going to try and fuck as many of them as I could, so I made up something else on the spot. It was a fantasy where I'm waiting in a room, naked and blindfolded. Women come in, one at a time, for oral sex. They can come back for another turn later if they want. I'm just there to eat the pussy in front of me. I figured I could play it by ear from there.

"Damn, Stephen, that makes me wet. I think we can arrange that," she said. She wouldn't be taking a turn; she didn't want her friends knowing just how close we were.

The doorbell rang at a quarter to seven; somebody was early. I'd asked Michelle to let me open the door. I couldn't keep my erection under control, so I would just have to greet them with a hard-on. I opened the door to a stunning African-American girl with a knock-out body. She was pretty shocked, it showed on her face. She looked me up and down, settling on down.

"Hey I'm Stephen, Michelle's brother. C'mon in."

"Samantha," she said, breaking into a smile as she stepped over the threshold, "Mmmm mmmm."

She was taller than average, maybe 5'7"; her skin was a beautiful rich dark brown, and she'd put copper highlights in her shoulder-length hair. Halle Berry and Serena Williams rolled up into one incredible package. We made eye contact as we shook hands, neither letting go for the longest time. It was electrifying.

"Top of the stairs," I said.

She looked back with a seductive smile as she walked towards the staircase, dropping her eyes to my dick then back to my face before starting up.

I went to the den and collapsed into a chair, shaking from the excitement. Seven more times the doorbell rang, and I greeted each lovely young lady with a smile and a hard-on. They were all surprised, and all seemed pleased, but none were more surprised than Gabriella, the other girl whom I had not yet met. I'd lost count, and was lounging in the den when I heard my name. I didn't recognize the voice, but it didn't matter; I went upstairs to find nine hotties smiling at me.

Ashley announced, "We talked about it and decided that instead of playing the game, we're just going to compare...mmmm...techniques, if that's all right with you."

As I looked around the room at the faces my brain was just so overwhelmed, I couldn't speak. My dick was buzzing; I was sure everybody could hear it. Michelle took my arm and guided me to the pool table.

"Hop up," she said.

I complied, surprised to see padded wrist cuffs and ankle cuffs tied to the table legs.

"Where did these come from?" I asked.

"I borrowed them," Michelle answered, then leaned over and whispered, "From Stephanie."

Jennifer took the lead. She was tall yet graceful, her straight brown hair framing a very pretty face with brown eyes and a wide mouth. When she put her hands on me, I let out a long, heavy sigh. I lay on the table as one pair of hands after another either demonstrated a cock-teasing technique, or tried one out for the first time.

The first time I came was early on, maybe the third girl to wrap her fingers around my cock. I let out a huge groan, and shot a load of cum that hit my nose, mouth and chin. It was her first time; I think it scared her a little. A sizeable puddle accumulated on my belly and chest. I saw Michelle approaching with tissues, but Jennifer shook her head with a sly smile. They were going to leave the cum on my face and body. My second orgasm was almost as explosive, enough to hit my mouth, which was open, unfortunately.

When Samantha stepped up to the table, I smiled, but was a little worried. I thought she would play rough, but she had the softest touch of them all. She had me edging very quickly, and all the other girls gathered around for a closer look at what she was doing. I had no idea what she was doing but I did not want her to stop. She edged me several times, answering questions, until they all thought they could do it. At least four of them tried it, and they all got it right. I was begging for somebody to make me cum. Chris, the quietest of the bunch, walked up and with one finger started tracing lines on my cock, in a seemingly random fashion. But she must have known what she was doing because about two seconds later I had another mind blowing orgasm. Not much cum, but it felt very intense.

I was a mess; there was quite a bit on my face, and the cum on my chest and stomach was dripping down my sides. I hadn't swallowed the cum in my mouth, and it seemed to be everywhere; I thought I would never get rid of the taste. After three times, I was pretty wiped out, but they kept going for a little while. It was a good opportunity for them to practice cock-teasing, so they took advantage.

I took a long, hot shower, after which Michelle asked if I was ready to start my "other project." I nodded. She handed me a scarf to use as a blindfold and walked me to the stairs. We'd decided to use the wingback chair in the master suite. Soon I was kneeling in front of the chair blindfolded. In a few minutes the door opened and a girl brushed against me as she took her seat.

"What should I do?" she asked. I didn't recognize the voice.

I told her to just sit back and relax, tap me on the head if what I'm doing isn't working for her, and hold me in place if it is. I lifted her knees to my shoulders and settled in. I took my time with her, and before too long she was crying out in pleasure.

"That...was...incredible," she said, panting heavily. She grabbed my head and bent down to give me a long wet kiss on the lips before rushing out.

A few minutes later, I heard a familiar voice, "Hey babe! Get that thing off your head." I stood, removing the scarf, and turned to greet Samantha. She had come downstairs in a robe, which she shed quickly, exposing that dynamite body. We embraced and I started nibbling on her neck. I don't know why we hit it off so well, but I felt like I'd known her my whole life. I told her how much I enjoyed her touch.

"Well now it's your turn," she said, taking a seat; I didn't waste any time getting started. I ate Sam until she came, then we moved to the bed. She was an animal - a predator - strong, agile and aggressive. Knowing what she wanted and how to get there, she took the lead and I didn't challenge her. After she came, I sent her back upstairs; I wasn't sure how many more times I could cum and still perform.

I took Jennifer to bed, and two others, both of whom kept me blindfolded. Sam returned for another round; I came inside her this time and that revved her engines some. Next to Sam, the other three were pretty much plain vanilla. That's not a complaint, just a description. All in all, I fucked four of the eight, and Sam twice. I made a mental note to do something nice for Michelle, I really owed her for this.

I lost count of how many times the door opened and another pussy came in. It was certainly more than eight. Apart from Sam, I'm not sure who came back for seconds. I just know I spent a long, long time with my face buried in pussy before Michelle came down and told me they were done. My tongue was sore as hell, but for the first time since Denise introduced me to it, I'd had enough pussy. I made my way back upstairs and marveled at the flesh strewn across the floor. They weren't sleeping of course, they were talking.

I saw someone beckoning to me, I think it was Caroline, or maybe Monica. She was stretched out on a quilt, covered with a light blanket. She wanted me to crawl in behind her, so of course I did. I snuggled up behind her and was surprised when my dick encountered the bare skin of her bottom. It felt so nice, as did her breast with my hand on it. I put my head on her pillow, my face in her hair, and promptly fell asleep. I somehow managed to wake up with a different girl; I had no idea who she was.

I went to the kitchen, returning with a box of assorted juice drinks and some grocery store pastries. After distributing breakfast I collapsed in the middle of them, lying on my back, dozing while they talked. It seemed almost as though they had become oblivious to me, but at random intervals, one of the girls would use some part of my body as a pillow for a few minutes; a thigh or my tummy, or sometimes a shoulder. Her hair spilled over onto my skin in a way that felt incredibly sensual without being overtly sexy. They had become so comfortable with me, they all changed clothes while I lay there in the middle of room.

When the last girl was gone, I told Michelle I was going to schedule my own sleepover with her tennis team. I never did, though.

Chapter 30

Ashley answered the door wearing a tube top, miniskirt and no shoes. Michelle had talked me into calling her. I didn't have to take her out, according to Michelle, because she only wanted to sleep with me. I had my doubts, since she didn't take me to bed during the sleepover, but thought I'd buy her dinner anyway. I drove to her house Friday evening, feeling pretty good about my chances.

She looked hot: sun-bleached hair pulled back into a pony-tail and perfect skin with a deep tan. She had slender hips, a narrow waist and a big smile. She invited me in. I thought we'd have dinner at a restaurant on the beach, but she wanted to hang out at her house for little while. Her parents were out for the evening and she had the place to herself. She led me to a sofa in the living room. Our lips were locked before our butts hit the cushion. We made out for a few minutes, and when we came up for air, she found my erection with her hand. She was lazily tracing the outline with her fingers, while I was massaging her breasts. She had small breasts, but I couldn't hold that against her.