Virgin Seductions

"You have a girlfriend, Bob?" my new boss asked me.

"Yeah, Janet."

"Got some pictures? Show me."

I got my phone and swiped over to some pictures of her.

"Damn, she's a real looker, Bob. How did you ever manage to snag her?"

"We have known each other since grade school and started dating a couple of years ago."

"Got any more pictures?"

I showed him pictures from last summer's family party.

"God damn, she sure looks good in that bikini. So, tell me, buddy to buddy, is she as good in bed as she looks?"

I was startled by his question. If he wasn't my boss, I would have told him off.

"Not that it's any of your business."

"Yeah, but I can't help but wondering, with a body like that you surely want to take advantage."

"Well, we have fun," I reluctantly admitted.

"Like what? Don't tell me you two are still virgins?"

"Yeah. I mean, we have fun but so far haven't had sex." I didn't like how this conversation was going. Way too personal.

"Yeah, sure. You guys are virgins! Other than not sticking it in her, what do you do?"

I felt a sudden need to defend my masculinity. "Janet has given me a blow jobh and I play with her pussy."

"Man oh man, that must have been a turn-on, having that beautiful, sexy mouth on your pecker. So does she swallow?"

I was obvious I was getting seriously pissed.

"OK, don't get your buns in an uproar. Not my business. I was just so impressed with your girlfriend. Come on, let's get back to work."

Two weeks earlier Janet and I graduated from high school. My dad helped me get this job for the summer. It paid decently and I planned to save it all for college. In spite of being a nosy horse's ass, my boss Greg was a decent guy and help me transition to the work environment.

Janet and I had been best friends for years. Somewhere along the line she turned into a beautiful girl. I loved being around her and she was the one who asked me if we could become a couple. Lots of other guys wanted to date her and were clearly envious of my good fortune.

I'm not so sure what she saw in me, however. I was still putting on height and was skinny as a rail. Janet said all her friends said I was so handsome, so that was something. I wasn't much in the social skills and she drew me into her circle of friends.

During the next year she filled out more on top, now about B cup. And I wasn't quite so lanky, putting on fifteen pounds. We were still both virgins but began some experimenting the last few months. I loved playing with her breasts, my hand under her bra. Eventually the bra disappeared and she encouraged me to suck and lick her nipples. I was in heaven and was encouraged to explore further.

One night after seeing a movie we were parked in her driveway. We kissed and exchanged tongues. We were both turned on and I unbuttoned her jeans and slid my hand inside her panties. I touched pussy for the first time. I played around and slid my finger between her pussy lips. I didn't know how far Janet would let me go but was encouraged when she pushed down her jeans partway to give me better access.

"Right there, Bob. Put your finger in my pussy. Now go in and out."

She grabbed my hand, my finger still inside, and held me against her pussy. She scared the shit out of me when she came. I thought I had hurt her or she had some sort of convulsion. Goes to show how naive I was.

"Kiss me, Bobby."

As we kissed her hand found my crotch. She rubbed the bulge, making it even bigger.

"I want to see it, Bobby. Show me your cock."

Naturally I quickly pushed down my jeans and shorts. My cock popped out, hard as a rock.

"Oh, it's so big," she murmured, touching it for the first time. Does it hurt when it gets so hard?" She was now gently sliding her hand up and down the shaft.

"No. Oh, Janet, that feels so good." Better and much more exciting than when I did it.

"If I keep doing this, will you squirt?"

"Yeah."

She scooted down and took me in her mouth.

"I've wanted to do this for months, Bobby. I probably won't be very good this first time."

The feeling of her tongue and mouth on my cock was heavenly.

"You like?" she momentarily took me out of her mouth.

"God, yes," I croaked as she smiled and resumed sucking. All too soon I was ready to explode.

"Uh, Janet, I'm about to ... I'm going to ....," my warning was too late. Her eyes got big and she gagged as I thrust my cock deeper into her mouth. She gagged again, her eyes watering. Cum dribbled out the corner of her mouth.

"Oh, honey, I'm sorry. Are you all right?"

"Yes, I'm fine. Just got surprised. You sure squirt a bunch. Next time I'll be ready."

"You were awesome. What did I taste like?"

"Like sex. Some of my friends suck their boyfriends. I told them I wanted to try and they said that I should swallow. Guys like that, they said. Kiss me and taste yourself."

****

I'm having a pool party on the 27

th

. You and your girlfriend are invited."

"Oh, ok, thanks. What's the occasion?"

"Just an opportunity to socialize with everyone. My wife Barbara and I will do some grilling. You don't need to bring anything besides yourselves and swim suits."

I had heard about Gregg's big house that he inherited from an uncle. Janet and I were excited to be invited.

"You need a new suite, Bobby, and I definitely need a new bikini. I've outgrown the old one," she giggled. "You can show me off to all those old guys."

At 18 we were the youngest by several years and no doubt Janet would be noticed. The day of the party she showed me her new bikini. God, she looked so sexy. She isn't real big on top but her B-cup breasts looked awesome on her slender body.

"I had to do some trimming, Bobby," she pointed to her crotch. "Pubic hair was peeking out on both sides of the tiny bottom triangle. I was thinking of doing it anyway. Seems like most of my friends have gone totally bare. Supposedly the guys like it, especially the ones who eat pussy. Maybe that's something we could try soon."

"Wow, this is quite a place," I exclaimed as we entered Gregg's sprawling home.

"Yeah, awesome. I suppose you know most of the guys?"

"Those that work in my group. Oh, there's Gregg. Let's say hello."

"You must be Janet. Even more lovely than Bob's pictures. My wife Barbara is around here somewhere. You'll like her."

He introduced us to some couples nearby and then left us to mingle. Janet and I felt a little out of place, being noticeable younger than the others but everyone was nice. We worked our way outside to the patio and pool. Great place. We were handed a couple of beers.

"Better go slow, Bobby. We aren't used to drinking." "Yeah."

"Oh, Hi. I'm Barbara, Gregg's wife. So glad you could join us."

She was a strikingly good-looking woman of Gregg's age, about 25 or so. I introduced Janet.

"You two make a very attractive couple, very handsome. Please enjoy yourselves. Later most of us will use the pool. Did Gregg tell you to bring suits?" We nodded.

By late afternoon some guests had left and those that stayed changed into swimwear.

"Oh, Bobby, I'm getting cold feet. I did so much want to show off a bit, but, god, this suit is so tiny."

"Actually, honey, you look terrific, very, very sexy. I don't mind people knowing what a great body you have."

"Well, if you say so," she responded dubiously. "It doesn't leave hardly anything to the imagination. But you stay really close in case I want to leave."

"How you guys doing?" Gregg asked. "Wow, Janet, you look ravishing in that bikini. That suit was made for you. You could be a model for Victoria's Secret. You are going to make all the women here jealous. Oh, I wanted to tell you that I made some tequila shooters. Want to try one?"

I looked at Janet, not sure if this was a good idea but what the hell it was a good party. Janet nodded. Two tequila shooters went down quickly, Janet had one. We walked around, chatting with co-workers and meeting new people. Janet blushed as guys blatantly looked her up and down but I was proud of my girl and didn't mind them ogling.

As the party wound down, we went to say goodbye to my boss and his wife. I guess the drinks had affected me more than I realized as I slurred our thanks.

"Bob, I don't think you should drive home right now. "Go lay down for a few minutes and you will feel better." Gregg looked at Janet for confirmation. "He'll be alright, my fault. At his age those shooters were way too much. Come back to the party."

****

Bobby becomes a man

Sometime later, I don't know quite when, Janet lay down next to me on the bed. "What are you doing, honey?" She pulled down my trunks.

"Relax, Bob. We are going to have some fun."

"What? Who? Ah, Barbara, is that you?" I started to get up and she pulled me back down.

"Just cool it, Bob. I just want to see that big cock of yours," she explained and put her hand around my quickly growing member. "Yep, as big as I guessed it was. You're even bigger than my husband."

I started to get up and she pushed me back down. "Don't be silly. You and I are going to have some fun. You a virgin?"

"Uh, yeah."

"I can't believe you and your girlfriend haven't had sex yet. Normally I would want to suck you first but this being your first time I want you in my pussy."

She undressed and straddled me. Taking my cock in hand, she positioned it at her vagina. She lowered herself and my cock slowly entered.

"Oh, no, we can't." I belatedly came to my senses. "I have a girlfriend. I can't do this."

I was trapped, Barbara above me and my cock now fully in her pussy. I struggled but not too hard.

"Don't worry about Janet. Right now focus on my pussy and your cock. I want you to enjoy your first fuck."

****

Janet's Seduction

I went back to the party with Gregg. I liked the guys ogling me in my tiny bikini. I even noticed a couple of guys had bulges in their trunks as they huddled around me. Being a sex object, I decided, was ok. One by one the couples departed the party and suddenly I was alone with Gregg.

"Where's your wife?" I was uncomfortable with how he was looking at me.

"Oh, she's around here somewhere, probably putting some things away. Come with me." He took me by the hand.

"Where are we going?"

"Don't worry, Janet. You are beautiful, so sexy, and I would really like to have some fun with you." He gently moved me towards the master bedroom.

"I can't, Gregg. I need to find my boyfriend and go home."

"Bob is busy right now with my wife."

"What do you mean?"

I was slowly being nudged down the hall and into a bedroom.

"She is very much taken by your guy. I'm sure by this time his cock is very busy inside her. Don't worry about him, he's a big boy and it's high time for him to learn about sex. You are so sexy, honey. Take off your top and show me your tits."

For the life of me I don't know why I didn't bolt out of the room, grab Bobby, and get the hell out. I didn't and moments later my 18-year-old breasts were on display.

"Oh, Janet. They are so perfect. Just the right size for your slender body." He bent over and licked one nipple, then the other. I was both mortified and thrilled by what this handsome man was doing. He dropped to his knees and pulled down my bottoms and laid me on the bed. He quickly removed his trunks. My eyes immediately focused on his hard cock.

"I'm a virgin, Gregg. I want Bobby to be my first. Whatever you do, please don't put your thing in me." I was relieved as he kissed down to my crotch. I knew about eating pussy from my friends and spread my legs to give him access.

I had let Bobby finger me but Gregg's tongue was so much better. He licked up and down between my lips and tongued my hole. I spread my lips to give him better access. In and out, up and down, and now his mouth was on my spread pussy. Oh, my, the feeling was exquisite. I was on the verge of a huge orgasm when he changed position.

I felt his cock press between my pussy lips. "Do you want this?" When I didn't respond he took this as a yes. A moment later I felt a sharp pain as he penetrated me. Oh god, he's fucking me. This isn't right. It's supposed to be Bobby.

"Don't do this. Please take it out," I implored, all the while knowing it was too late.

He ignored my feeble protests, sensing my acquiescence. I forced myself to relax, his cock deeply embedded in me. My body betrayed me and responded as he fucked me. "Oh .... Ohhh .... " I grabbed his ass to pull him deeper, each thrust sending me higher and higher. Never had I experienced anything equal to this. I exploded in orgasm as he slammed into me and filled my virgin pussy with cum.

I gradually became aware of my surroundings. I was in bed with a strange man, Bobby's boss, his cock still inside me. I was no longer a virgin. All our plans were wrecked.

"It's ok, Janet. You were ready for sex and so was Bob but neither had the initiative to do the deed. I'm sorry it hurt but you had your first orgasm. That felt good, didn't it?"

"I need to go to Bobby and go home."

"Barbara is still with him. We need to wait until she returns."

"Are they having sex?"

"Oh, I'm sure. Probably a couple of times."

Gregg stayed inside me, his half-hard cock gently moving in and out. I felt it gradually stiffen and my pussy again responded.

"We have time to do it again. This time I want to do you from behind."

He nudged me onto my tummy and moved my legs apart. No protests this time, I was in complete submission, a sex doll to be manipulated and used. A moment later he penetrated and I had my second, mind-blowing orgasm.

"Honey, you have a body made for fucking. I love your young pussy, so snug, so juicy. You liked it didn't you?"

"Yeah, I did. But I am so bad to let you do this to me. How can I ever look Bobby in the eye?"

I turned over and saw his wife standing in the doorway, nude. I closed my legs, embarrassed by my exposure.

"Janet, you are the sexiest little thing. Don't worry about your boyfriend, we just fucked. He did great with that big cock of his. He's waiting for you now."

I looked at her, full of doubt. Did Bobby really have sex with her? Guys were different, always wanting pussy. But girls were supposed to be pure and wholesome. Here I was with a pussy full of cum, my virginity gone. Barbara apparently read my thoughts.

"Honey, he wants you and needs you. You are feeling guilty, I understand that, but no more so than he does. Go to him and let him fuck you. Everything will be ok."

"I better clean up," I got up from the bed.

"No, go just the way you are." Barbara said.

"But I'm full of your husband's stuff. I'm dripping."

"And my pussy is full of your boyfriend's cum. Go to him and give him sloppy seconds while Gregg gets seconds from me."

****

The aftermath

Janet hesitantly opened the bedroom door. I jumped out of bed, still nude.

"I was worried about you. Where have you been?"

"With Gregg."

"Oh. You mean you and Gregg ...?"

"Yes. He took my virginity, Bobby. I could have stopped him but I didn't. His wife said you and she fucked. That true?"

"Yeah."

"So, neither of us are virgins anymore. That wasn't what we planned, was it?" She started to cry.

"We both made a really bad mistake. I'm so sorry, honey."

"And I'm sorry too. Can we get passed this? We still love each other, don't we?"

"God, yes! You are everything to me."

"Bobby, would you like to make love to me? I was so naughty and my pussy is still full of his cum." She placed my hand on her still engorged pussy. "He fucked me twice and she said she fucked you twice. She said her pussy was full of your cum and wanted Gregg to have sloppy seconds. Would you like sloppy seconds?"

Moments later my rock-hard cock was embedded in my girlfriend. She cried as I gently moved in and out of her cum-filled pussy.

"I love you, honey. Everything will be OK."

****

We woke early, still dark, with me spooned against her, my hand on a breast.

"Not what we planned, was it?"

"No. Forever and forever you were going to be my first and only and we would marry. I can't believe I let it happen. I had plenty of opportunity to stop things but didn't. Worst of all, the second time I really liked it." Janet sobbed.

"What's done is done, we can't change last night. Tell me what happened."

She continued to sob. "He took my virginity. It hurt but the pain quickly went away and I got excited. I intended to get back to you but he said we needed to wait until his wife returned. That you and she were having sex. He remained inside me and a few minutes later we did it again and I liked it."

"And he came in your pussy?"

"Yeah, both times. I guess if I get pregnant it's his fault," she admitted. "I don't think we have anything to worry about since my period is due in a day or two. I felt so guilty that I ruined everything. I was surprised that you didn't get mad."

"I was no better."

"Tell me what you did."

"She pulled down my trunks. I was still in a fog from the liquor and didn't stop her or even think to ask where you were. I just laid there as she got on top and rocked back and forth. I didn't last long. Afterwards she fondled my cock until it was ready again and then I fucked her from behind.

"If anyone's at fault, it was me. I should never have had those shooters. I was so relieved when you returned. You looked so sexy standing there, your pussy red, his cum dripping out. I know this is awful to say but it turned me on. I wanted to be inside you, for us to have our first sex."

"Our first time but sloppy seconds," Janet giggled. "We were so bad. Now let's do it again."

Afterwards we laid side by side as she gently fondled my cock. About that time Gregg and Barbara entered our bedroom. Both were nude.

"You guys doing ok?" She asked and moved to my side of the bed. "God, Janet, your guy has the best cock, so big. You are so lucky." She placed her hand on top of Janet's as they both gripped the shaft. Janet turned and stared at Gregg's huge erection.

"We were hoping to have some more fun," he said and laid down next to her. Without prompting she took his cock in her other hand.

"I should be really mad at you, Gregg. Bobby was supposed to be my first. Somehow it didn't work out that way."

She turned onto her tummy and spread her legs. My boss looked at me and I nodded. Inch by inch, his cock entered my girlfriend.

"They look good together, don't you think? It's been a long time since Gregg's had such young pussy. Now our turn. I'll get on top so you can continue to watch."

She straddled me, facing away, positioned my hard cock at her vagina and slowly lowered herself.

"God, you have such a great cock. I think you are bumping against my cervix."

I didn't know where to focus my attention, Gregg's cock thrusting into my girlfriend or mine sliding in and out of his wife's tight pussy.

"Gregg, let's switch." Barbara suddenly lifted off my cock. He pulled out of Janet and I shoved my cock into her now gaping pussy. I was determined to equal the skill of my boss. Using my full length, I pulled out until just the head was inside, then pushed deep.

"Oh, Bobby, you feel so good in me. Fuck me hard."

Janet made little squeaky noises and humped back to meet each thrust. She suddenly clamped down on my cock. "Oh, god, honey, that is so good. Oh ..." Moments later I too climaxed. I slumped down, utterly exhausted, my cock still inside. I noticed that my boss and his wife were gone.

****

Monday

I didn't know what to expect Monday when I went in to work. Gregg paid no particular attention to me and nothing was said. The guys from the party said I was the luckiest guy to have such a luscious girlfriend. I agreed.

Janet got a birth control prescription. One week, ten days to be sure, and we could safely have sex. Two or sometimes three times a week my parents or hers were out and we had a place for sex. About three weeks after the party Gregg asked me to stop by his office after work.