Extra-marital Cherry

EXTRA-MARITAL CHERRY

Hi! I'm Jill, the subject of this story. It's my extra-marital cherry that we are talking about. There are different kinds of firsts. Losing your cherry refers to first sexual intercourse. But there is also your anal cherry and your extramarital cherry referring to having sex with someone other than your spouse after you've been married. That's what happened to me recently.

I was with Russ, a friend of ours. His wife Lisa was in another room with my husband John. They were doing the same thing Russ and I were doing, soft-swinging that was possibly going to cross the threshold to having sex and become actual swinging. I'd never had sex with anyone but my husband, so if I gave it up to Russ, it was kind-of a big deal.

My blouse and bra were lying on the floor. Russ had removed them and was fooling with my tits. I don't like to brag about my boobs, but a number of guys have told me that I have a magnificent pair. I am a D-cup and my soft breasts do hang nicely with dark pink areolas and nice big nipples that stick up in the center. Russ was fondling my boobs, rubbing his face on my chest and licking my nipples. My breasts are very sensitive and I absolutely love it when someone plays with them. It's only been through dumb-luck that I haven't been seduced by some other man playing with my tits.

Russ had his shirt off too and was partially on top of me. His leg was between mine, pushing up against my crotch and his hands were all over me. He was a good, passionate kisser. I could feel his hard prick against my leg. He quite obviously wanted me, to take my cheating-cherry and become the first man to fuck me other than my husband. He knew he would be the first and it really seemed to turn-him-on to think that he might go where only my husband had been. I was aroused myself and after some wine at dinner, was in the mood for sex myself.

My husband, John and I had talked about swinging or having a threesome, inspired by some of the dirty stories we read on-line and in magazines and by some of the porn we had watched together. John likes to look at porn more than me and would really get aroused by stories or movies where a wife is taken by another man. He says while he likes watching porn, he gets much more excited by thinking about me doing some of the things he reads about or watches. He says he imagines it's me in the stories and asks if I would like to do the things in the videos. I always tease him by saying 'maybe' and that I would like to do some of the things with specific men in the videos. I would comment about how I would like some porn star's cock in my mouth or my pussy. I have and exhibitionist streak in me and like to be watched so having John watch me have sex is arousing. I'm willing to wear sexy clothes and flirt with other men while John is around. It inevitably results in some very steamy sex when we finally are alone.

I'm 45. I was a school teacher, but now I work for an educational testing firm that had contracts with the federal government. John is an engineer who works for the county government. He travels some. Our three kids are grown, with the youngest away at college. With an 'empty nest' we began to look for thing to replace our children as the focus of our lives. We started to go out dancing and went to dinner with friends. We've travelled and have taken-up tennis and golf.

We have casually known Russ and Rita for years. Russ is John's boss. Rita is a buyer for a department store. We didn't realize for a number of years until we got to know them better, that they are swingers. As we became closer to them, their hints and innuendos became more explicit and they have told us about their adventures with other people. Of course, once we realized what they were into, there has been the potential for John and I to become involved with them. We told them we were not into swapping and they said fine and never have pushed us. Rita did tell me once that Russ would really like to get me in bed, if I ever had the urge and she said she would like to fuck my husband if I was okay with it.

John and I had joked about it frequently. When he was late coming home from work or something, I would tease him by asking if he had been 'shacking up' with Rita. When we would go out to dinner with Russ and Rita, my husband would joke about how Russ would be checking-out my ass or my boobs. I would wear short skirts and loose blouses. Any time I showed cleavage, John would joke about Russ looking down my blouse, but he would jump me when we got home. I knew it turned him on to have another man ogling my body and thinking about getting in my pants. John and I never had the nerve to suggest that we actually try anything with Russ and Rita. We were scared, but the possibility was always there, more-so lately.

We had gone to their house after dinner and the soft swinging just happened. I danced with Russ and before I knew it, we were kissing and then were on the couch with him taking off my clothes. John and Rita were on a love-seat across the room. I would occasionally look over to see what they were doing. I wanted to pace what I let Russ do with what John was doing with his wife.

We ended the evening by not going any further. They didn't want to push us. Like I said at the beginning, Russ had stripped me to the waist and played with my tits. He really was entranced with my breasts and nipples. It had been years since anyone other than my husband had fondled my breasts. It was exciting and arousing, but I still had a reserve of reluctance.

After necking like that for an hour, I had rubbed Russ's cock through his pants and he came. The unmistakable look on a man's face when he comes is priceless. Once his urges had been tapped, we calmed down. My husband had gotten further than I did. He had his fingers inside his boss's wife's cunt and she had his exposed prick titty-fucking her. We'd gone as about as far as we could without going over the edge to fucking. We said polite good-nights. We'd hadn't felt pressured and Russ didn't push me to go faster of further than I was comfortable with.

I reflected on our way home. I'd only been with John. No other man had ever fucked me and only a few had even seen my tits. I was scared of going further, but at the same time, I was drawn to it sexually.

John didn't say much other than asking if I was okay. I was.

I asked him, "Did you see Russ playing with my tits. He really liked sucking my nipples."

John said, "That was hot seeing you get stripped like that and watching you enjoy someone relishing your body."

"You seemed to be doing pretty well yourself. Did you have your fingers in her cunt?"

He said, "I did."

"Why didn't you fuck her?"

"I wouldn't do that unless you were doing the same thing. We're married and should do things at the same pace."

I said, "You know no other man has ever seen me naked or fucked me. How would you feel about someone taking my married cherry?"

He said, "We have to really think about where we are going and if we are both comfortable with it."

I felt his cock through his pants and knew he was excited by the idea of swapping with Russ and Rita.

A few days later, Russ and Rita invited us to join them at their place on the Outer Banks of North Carolina. Rita previously mentioned that they would like to invite us, but wanted us to be comfortable that we wouldn't be pressured to swap with them or anything. Rita said, "Believe it or not, we don't fuck everyone we invite to our beach house." The idea of spending a few days at the beach was intriguing. John and I hadn't been able to spend time together at the beach, without kids, since our honeymoon, years ago.

I asked John if he thought we should go and he said he would like to.

I mentioned. "What about the swapping thing? We almost did it last time we were with them."

He said, "We don't have to do that if you don't want."

That was an interesting response from my husband, indicating that he was open to the possibility of swapping all the way. I knew he was intrigued by Rita and was turned-on by the idea of watching me with another man.

Rita keeps herself in good shape and I've seen my husband checking-her-out. She often wears blouses that provide a good view of her tits when she leans over. Her breasts are smaller than mine and she has nice legs that are often on display. She will wear short skirts and one time she teased him about whether she was wearing panties or not. John told me he happened to brush his hand against her ass and could not feel any underwear. There was no doubt that Rita would like to fuck my man.

The impediment to swapping was me. Although John was interested, he was conflicted between his desire to fuck Rita and his reluctance to let another man be the first other than him to fuck his wife.

The morning of our trip to the beach, I asked John, "What do you expect will happen with Russ and Rita. What if they want to fool around?"

John said, "I don't know. I don't want you to do anything you don't like."

I said, "So if there was something I did like, it would be okay, huh?"

He said, "I could see fooling around a little, but not going too far."

"You'd like to nail Rita, wouldn't you?"

He paused to consider his answer. "I guess I would, but I don't want to mess things up between us."

"What if I was okay with you screwing her?"

"Then what would you and Russ be doing?"

I asked him, "What would you like me to do?"

"Only what you want."

"Would you like to see him fuck me?" We were finally getting to the point.

My husband said, "I'm not sure. I like those stories about guys watching their wives get fucked by other men. You seem to like them too, don't you?"

I said, "I like them because you like them. I like the thought of you being turned-on while watching some other dude fuck me. Would you like to see that?"

He said, "I think I would, but only if you would enjoy it."

I smiled and said, "I think I could get into having Russ strip me and fuck me while you and Rita watched. You could watch his cock slide into my little pussy."

John groaned and said, "That would be so hot."

"He would be the first man to fuck me other than you. He'd be taking my cheating cherry, the first man to fuck me outside of my marriage vows. Do you want to see that?"

John said, "It scares me to think about it. It really turns-us-on, but I don't know how I'd feel about someone else having you."

I said, "Just think, you are the only one to have seen me naked, to have looked at my tits and my pussy. Your cock is the only one to have been inside me. Imagine another man's cock slipping between my pussy lips and sliding into my married cunt. No one has ever come inside me other than you. Would that turn you on to think about another man's cock trying to knock-me-up, to have his sperm swimming up inside my womb?"

John just groaned. I knew he wanted to hear more.

"Just think of me lying naked in bed with another man, letting him take me. He could touch me anywhere he wanted. He might put his tongue inside my nasty cunt and lick me. I'd cover his face with my cum. My pussy would gush all over him. Maybe he'd want to fuck me in the ass. Think about that, another man eating your cheating wife's cunt and then fucking her in the ass."

He said, "You don't let me have your ass. You'd let him?"

I teased him more, "I would be his for the night. He could do any nasty thing he wanted to. He'd make me suck his cock and swallow his cum (another thing I don't do very often). I'd come to bed with you the next morning all full of another man's sperm in my vagina. Maybe I'd make you clean me up, suck all his cum out of my unfaithful pussy."

He was rubbing his cock. He'd gotten it out and was jacking-himself-off.

"Do you wonder how big his cock is? I felt it through his pants and made him come. Maybe he'll reach places inside me where you've never been, places where only a man with a bigger cock can reach. He might stretch me out to where I wouldn't feel your little dick when you fuck me. I'll bet he would make me come, over and over, like you used-to-do."

He was getting defensive and said, "I still make you come?"

I was taunting him, "You do lover, but I'm thinking of coming on another man's cock, a new cock inside your cheating wife's snatch."

He looked at me, starting to get worried that I was serious.

"I could get you promoted by fucking your boss. Maybe he'll want me all the time. I could be his plaything. He'd invite me into his office and fuck me while you are out somewhere hard at work. Everyone you work with would know that your boss is fucking your wife."

My husband came, hearing about his wife fantasizing over her first time with another man. The gooey semen spit from his onto his leg and hand.

I said, "Oooh, look at you coming thinking some other man fucking my married cunt. Are you thinking about getting sloppy-seconds from your wife's pussy?"

He said, "Wow. It's so hot. Should we do it?"

I giggled and said, "It would just be sex."

John said, "Let's just see what happens and how we feel when we are there."

I knew the idea turned him on like crazy. My dirty talking had almost persuaded me that it was something I wanted to do, to let another man fuck me, ravish me. It would all be new and exciting.

We met with Russ and Rita for the drive to the beach. We took two cars, loaded with food, drinks and such. To keep from getting lost, Rita rode in the car with my husband and I rode with Russ. I was wearing just a pair of gym shorts and a halter top, with underwear, of course. The men were wearing shorts and polo shirts. Rita was wearing a very short skirt and a tight white top.

We followed them from Virginia. After getting through the usual small talk about the weather and what to expect at the beach house, Russ motioned to the car ahead, where John and Rita were clearly engaged in a lively conversation. "I wonder what they are talking about." He asked.

"It sure looks like they are having a nice conversation."

Soon after, we stopped at a rest-stop. I asked my husband what he and Rita had discussed and he gave me a general answer saying they were taking about his and her work. I saw Russ and Rita give each other a sensuous kiss. That aroused me a little so I gave John a nice kiss. I pushed my body against him. I could tell he was 'hot', and so was I. He smiled at me and said, "Have a good time." That made me suspicious of what was going-on in the front car.

We started off again. After about fifteen minutes, we saw Rita reaching her hand out of the window and holding something white. Russ didn't say anything but I knew what she was holding, her panties dangled from her fingers. She pulled her arm in and tossed the panties in the back seat of their car.

Russ said, "Dammit. I told her to behave herself. She has the hots for your husband, but I told her he was off limits. We don't want to pressure you two into anything."

I said, "It doesn't look like she's forcing him to do anything."

"Well, anyway, I apologize for my wife."

We drove a bit and I said, "I know John has the hots for your wife too, so I'm the prude of the bunch."

Russ said, "Don't talk like that. You shouldn't feel pressured into doing anything that you don't want to do."

I knew the answer to my question but asked it anyway. "What are your intentions with respect to me?"

He thought for a moment and said, "I have no expectations or intentions. If something happens, fine. If not, that's okay too." After a moment he said, "I do find you incredibly attractive."

"So, you'd like to take me to bed. You're bringing me down here to seduce me."

"Of course, but only if you want to do it. I had a marvelous time with you last week and would be fine with just that, if you were interested."

I asked, "What if John sleeps with Rita? Would you expect me to reciprocate?"

"Not at all, but I don't think John will do anything unless it's okay with you."

I said, "Once again, I'm the prude."

He said, "Don't think of things that way. It would just be uncomplicated sex, nothing more."

"It would be a big deal for me. I've never done anything except with my husband. You'd be the first man in my married pussy."

"That's what would really be special for me. I'd like to be the first man other than your husband to make love to you, the first to undress you and lay you on the bed, the first to taste you, the first to enter you and feel the heat inside you."

Wow. He was enticing me with his comments. I asked, "Have you been the first with other wives?"

Him: "Yes. A few times. It's really special to bust a woman's extramarital cherry."

Me: "Tell me about the others you've done."

Him: "Well. Before I married Rita, I had a good friend and his wife wanted to have a threesome. I was the first guy to screw her after they were married. She was shy at first, but once she got going, she was a tigress."

Me: "How did the husband take it?"

Him: "He was okay with it. He liked watching me screw her."

He continued, "There was a guy who was an asshole that I worked with ten years ago. He was always ragging on me about my work and bragging about what a hot-shot he was. I fucked his wife for him. He didn't like it so I rubbed it in. I reminded him that every time he looked at his wife's vagina that he should remember that I'd had my prick inside her. I told him whenever he kissed her, he should remember where her mouth had been. Stuff like that. It was nasty, but he was an ass."

"Would you put down John, that way?"

Him: "Not at all. I really like working with him and have all-the-respect-in-the-world for him."

"You'd just like to fuck his wife."

"Absolutely; I'd like to be your first. I've had the hots for you since we first met, but I've had to behave myself since you are John's wife. If you and he would be okay with it, I'd relish the chance to teach you about the pleasures of sex beyond your marriage. Rita can teach you some things too."

That was a new thought. "Does Rita do it with other women?"

"She has."

"Do you like to watch?"

He said, "Yes. It's incredibly erotic to see two women making love."

I was quiet for a while. I had entertained the thought and he knew I was seriously considering having sex with him. His seduction was working.

Now I'm not prude. I've been on nude beaches with my husband and danced half-naked at a party one New Years Eve. I've done some soft-swinging with his brother one time and a friend of his, another time. The friend had me down to just my panties and I jacked-him-off while he played with my tits, like Russ had.

I decided to be a little daring. If Rita had taken off her panties, I could make my husband wonder about what was going on in our car behind them. I leaned forward and pulled up my top. I asked Russ to unhook my bra. I pulled it off my shoulders and removed it. Russ blew the horn at John and Rita so they would look back. I held my bra out the window for them to see and then threw it in the back seat.

I was laughing and Russ was smiling. My unrestrained tits jiggled under my top and my nipples were quite evident, poking through the thin front of my top. They were jutting out and jiggling with the movement of the car. I was truly aroused.

"Wanna see?" I asked Russ. He nodded so I pulled up my halter and showed him my beauties. He almost ran off the road looking at me. I pulled my top down to let him concentrate on the road.

We drove for a little while and then I saw Rita hold something out the car window again. I recognized it as her blouse. She waved it around and threw it in the backseat. I knew she was now riding topless with my husband in addition to being panty-less. I knew John would be out-of-his-mind with Rita beside him nearly naked. She only had that little skirt left. I wondered if she would be bold enough to take that off too.