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Watching Terry

Category: Group Sex
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Chapter 1

I’m a pretty relaxed guy, I don’t get upset about most things, I can usually go with the flow but I did realize that I did have an obsession that started about five years after we were married.

It started when I was looking through some boxes in the attic, trying to find my high school yearbook. I had a reunion coming up in a few months and wanted to refresh myself on the names and faces from my youth.

Then, I pulled out a box of slides, the old 35 millimeter kind. Holding them up to the light, I saw that they were shots of Terry, my wife. But before she was my wife, I was certain of that. Now the shots were sexy, no, not porn, just her looking sexy and gorgeous in a two-piece bathing suit, sitting on a chaise lounge between two guys.

There was nothing overtly prurient about the slides but my eye was drawn to Terry’s hand resting on the lap of one of the men in the picture. For, her hand was not only in his lap, it was very close to just where his cock would be. Truthfully, the pictures were, no doubt, perfectly innocent, taken on a nice, summer day, but it was me, my own mind, full of lascivious thoughts and desires, that fueled my growing obsession.

I wanted another guy to fuck Terry while I watched.

Yes, yes, I know, kinky, weird, maybe, whatever. But it’s what came into my mind when I held the slides up and it was what stayed on my mind. As I held the slide up, I felt my cock growing hard, my mind filled with thoughts of this guy, or some guy, taking Terry’s clothes off, kissing her all over, taking his clothes off, getting on our bed, him between her legs licking her as she groans, his hard cock dangling down until he raises up and pushes it up inside her open snatch and begins fucking her hard.

Oh, did the fantasy make me hard. Oh, yeah.

There were other slides of her, in her swimsuit, pretty sexy shots, she is gorgeous, and I wondered if anything might have happened between Terry and one of those men, hey, maybe both, who knows, and my obsession grew along with my cock.

As I sat in the warm attic, my mind began to create new slides, one of Terry between the two men, this one with her hand squarely resting on the guy’s bulge. Then, the guy putting his arm over her shoulder and dropping his hand inside her bra top, her unzipping his pants, reaching in and pulling his cock out and stroking it.

Maybe it was the heat in the attic combining with the heat of my fantasies, but I unzipped my own pants and hauled my own cock out and jacked-off as I held each slide up to the light filtering in the side window. My cum spurted out farther than normal, it was a really strong cum, I almost fell off the box I was sitting on. This whole thing had really, really turned me on. Much more than I had imagined it would. Well, well.

As I went back downstairs, it came to me that I didn’t feel at all jealous, envious that one, maybe both these men might have had sex with my future wife, no, it made me horny. I was turned-on. Usually a good masturbation calms down my best friend. This time, however, I walked down the stairs into the house with an enormous hard-on. Amazing.

Over the next few years, these thoughts, these fantasies of my wife getting fucked as I watched continued. There were many times when we were fucking that I was imagining some other guy stroking in and out of her as I sat and watched.

One night, after fucking, I asked her about her times with the men she had dated.

“You really want to know all that? You won’t get mad or jealous?”

“No, hon, I promise. I’m just curious, I mean you’re a sexy woman, guys would be attracted to you, I sure was. So, tell me.”

“Well, okay. Just stay cool. Um, let’s see. Jeremy Knox, we were in the seventh grade. I had talked Mom into putting me on the pill, a bunch of us girls made up a scheme of symptoms that led to us getting prescriptions. Then, well, I actually picked out Jeremy from the boys in my class because I thought he was cute, and invited him over after school. Both parents worked, so it was easy.”

“So how did you get him in the sack?”

“Well, I figured I would start us talking about sex and just ask him if he’s ever done it. He said he hadn’t and I asked him if he wanted to, with me. Being a boy, you know what his answer was. We were quickly naked and fucking on my bed. There were several of us girls who had taken measures with one girl’s mother’s dildo to prepare ourselves for our first time by getting our hymens out of the way well before our first fucks.”

“You seem pretty determined.”

“Oh, you just don’t know how girls think. Anyway, Jeremy and I did it and it was pretty good. It really got much better after the first time when he would give me oral sex first before he fucked me. It was then that I was convinced that I wanted sex and I wanted it a lot.”

“So how long with Jeremy?”

“Um, about a year and a half. Then, we moved away. I was heartbroken, mostly about losing his dick, actually. But, you know how teen girls are, I quickly found a replacement, Adam Chappell.”

“So, how did it start with Adam?”

“Well, he came up to me one day at lunchtime. I was new in the school, maybe three weeks or so. He introduced himself and asked about me, where I was from and stuff, and we just chatted for a while. He was nice, really nice, actually. We had lunch together for several days and then he invited me over to his house after school.”

“Aha, he makes a move.”

“Right, and I was pretty sure that’s what it was and it was fine with me. I really missed the afternoons with Jeremy, so I walked home with Adam and as soon as we were inside, he put his arms around me and kissed me. I mean this was eighth grade, he knew what he wanted.”

“Oh, and you didn’t?”

“Well, sure, I went right along, pushed my tongue right into his mouth, pressed my middle up against him, even rubbed it around some, as I remember.”

“Oh, you little slut, you.”

“Like I said, I knew what I wanted, too. So, we stood there kissing and he soon put his hand on my breast and whispered something about going to his bedroom.”

“Aha, now we’re getting somewhere.” I was so hard listening to her story.

“Oh, it was just a few minutes before we were totally naked on his bed. I remember getting up on top of him and rubbing my pussy all around on him, I was so wet, it was incredible. We did sixty-nine that first afternoon and fucked right after. He was a real sex machine, horny all the time. He once fucked me three times after school before his parents got home.”

“Three times in, what, two and a half hours, wow, horny kid.”

“Don’t I know it. We did all kinds of positions, just fucked all the time, trying this and that, we were well-suited to each other, just like you and I.”

“I think we are, too.”

“So, after that was Wilson Brent, I used to call him Brent Wilson kidding him, that was high school, um, junior year. He gave me a note one afternoon that said, ‘Terry, you are TMFGIHS.’ I asked him just what it meant and he said, ‘The Most Fuckable Girl in High School.’ I didn’t know whether to slap his face or drag him off to a dark corner and fuck him to death.”

“I’ll bet he never got a slap.”

“Now how did you guess that,” she said, wrapping her fingers around my hardening cock.

“Are you getting hard listening to my tales of early sex?”

“I really am. It’s really turning me on, I’ve got to tell you, it makes me so hard thinking about other guys fucking you.”

“Well, that’s interesting. Have you always been like this?”

“No, just the last few years, I guess.”

“Other guys fucking me, it really turns you on?”

“Yeah, a lot. You’re feeling what it does to me,” and, indeed she was, I was hard as a rock and we had just screwed a while ago.

“Hmm, well, maybe I’d better save the rest for another time and get another nice fuck out of this,” she said squeezing my excited cock.

I got up on my knees between her legs, imagining I was Wilson Brent or Brent Wilson, or whoever, and pressed my titillated dick into her waiting and hungry pussy and proceeded to fuck her fast and hard. We both had massive orgasms no doubt because we were both reliving her former lovers fucking her.

We both agreed later that reliving her past with other men added a lot of spice to our sex that night. We would continue her tales of sex with men before we met and it always resulted in stellar sex.

The next step in my journey of fantasy was when I heard from a former college roommate of mine, Phil Aston, who was passing through and wanted to visit. I talked him into staying over night so we could catch up on the intervening years.

After dinner, I suggested that we change and take our wine out to the hot tub and Phil said, “Well, I didn’t bring any trunks with me.”

I replied, “Well, I’ll lend you a pair of mine, in that case,” and Terry jumped in with “Look, we’re all consenting adults here, right, come on, a little skin never hurt anybody, right. We all took sex-ed, after all,” and we laughed and took our glasses to our rooms and changed into skin.

While we were in our room, I asked Terry, “What made you come up with skinny dipping, hon? Do you fancy my old school chum?”

“You mean, like sexually?”


“Well, he’s a nice looking guy, kinda sexy himself, I am human.”

Here was my chance, “Wanna fuck him?”

“Are you serious, Stan?”

“Sure. Why not. It’s not like it’s behind my back. Why don’t you see what happens when we get in the tub, whatever you want to do is fine by me.”

We went out and got in the water, I noticed that Terry was careful not to submerge either of her best assets under the surface, no, she kept both breasts just touching the water underneath.

Out came Phil, not fully erect but about halfway, and I’m sure Terry was mentally measuring him as he walked toward the hot tub and got in with us.

“Don’t sit so far away, Phil, come over here,” and she patted the spot next to her on the other side of me. Phil stood up, now, even more erect, and moved next to Terry.

“I just love being in here with two handsome, naked men,” she said as she laid her head back bringing her breasts up out of the water, her nipples pointing to the sky.

She lifted her right hand up out of the water, brought it right over me and dipped it below the surface and I felt her wrapping her fingers around my cock. She started moving her hand up and down, rather obviously masturbating me, her hand even breaking the surface of the water once in a while.

After a few minutes of this, she turned to Phil and said, “I’m not being a very good hostess, am I, making Stan nice and happy and letting you just sit there? Here, scoot a little closer,” and I saw her left hand drop below the surface and then began bobbing up and down. She had both our cocks in her hands, jacking us both up and down.

The fact that Terry was jacking-off my old college buddy had me harder than ever. So I turned toward her slightly and began to fondle her breast.

After a minute or so, I said, “Phil, don’t let a perfectly sexy, beautiful breast go to waste,” as I nodded to Terry’s left boob.

He, then turned slightly and began rubbing her other breast as well.

“Mmm, this is nice, guys, really nice.”

I ran my other hand along Terry’s upper leg and she automatically widened for me as my hand dipped down between her legs and began exploring and enjoying.

Terry reached over for Phil’s hand and led it down between her legs, saying, “You two boys will just have to learn to share, okay?” and we both began rubbing her pussy under the warm water as she stroked us both up and down.

Soon, Phil and I both had a finger inside my wife’s pussy, of course, we both knew it, we had to, there was no other way. We were both finger-fucking my wife.

“Hey, Phil, what say we get Terry up on the rim and each take turns giving her oral? What do you say?” We each nodded and lifted Terry up on the back rim of the hot tub, resting her back on the wall and I waved our guest forward as he got down in the water between her legs and began licking her pussy.

Of course, I knew full well, just how much Terry loved oral sex, she just adored it and I was loving watching Phil do her as I stroked myself under the water.

She soon erupted in a massive orgasm, I knew it was massive, I’ve experienced hundreds, maybe thousands of her’s and this one was stellar. Phil continued on for a few minutes, then I took my turn between her legs.

As I started, she moaned, “Oh, mmm, mmm, oh, you guys are making me feel so, so good, I’m gonna make you two so happy, too, mmm.”

I did get her to cum and we finally got out of the water and dried off.

“Well, boys, after that, let’s all sleep in our room tonight, clothing optional, um, no, clothing banned,” she said and we both followed Terry’s pretty butt down to our room, stripped the duvet off and got in bed, me on one side, Phil on the other.

“Phil, you’re our guest, I’m sure Terry would be pleased,” as I swept my arm in her direction and Phil got up between her legs and pushed his rather sizable cock into my wife. I was making note of every move so I could play it all back in my mind and relive it whenever I wanted. I got so hard watching Phil’s cock sliding in and out of my wife, her juices glistening on his shaft.

“Stan, get up here and I’ll suck your cock,” she offered and I got up near her head and put my cock down so she could suck me as Phil fucked her.

Even distracted as I’m sure she was, Terry still gives the best blowjobs I’ve ever had, she’s a master. Though, truly, she’s fantastic at sex in every manner we’ve tried.

Phil was taking long, slow strokes in and out of her, something I knew Terry loved. She just never wanted to rush anything about sex, she loved it all so much. And, sure enough, she began to moan, even with a mouthful of my dick and then started humping Phil as she was consumed with another orgasm. Phil continued on until he, too, cummed her full, bucking into her over and over.

He fucked her for a few more minutes, then pulled out to let me pleasure her.

We swapped places and I shoved my hard, excited cock into her pussy, immediately driving it all the way up inside her, she was so wet, full of Phil’s cum, hot and slippery, I just started fucking her with determination and Phil knelt beside her, his cock swallowed up and being eagerly sucked as she played with his balls.

I was so turned-on by watching my wife getting fucked by my old college bud, that I just went fast and furious, fucking her like it was my first time. I hate to admit it but all I was thinking about was myself, my wanting to fuck her hard and fast, my wanting to spurt my cum up into her adding it to another man’s.

And I soon did cum in her, it was one of the best fucks of my life, I was incredibly turned-on by Terry and Phil and kept running the mental image of his cock running in and out of her wet pussy over and over in my mind.

We all slept together that night and Phil fucked Terry one more time before he left to continue his trip, I’m sure his head was spinning at the action he had visiting his old college buddy and his hot wife. I know my head was spinning from it.

What that night proved to me, however, was that Terry, under the right circumstances, she could be as sexually adventuresome as I had ever hoped. And I now knew just how turned-on I got watching another man fuck my wife.

We would often talk about Phil’s visit, especially as we lay together after fucking each other. She really did like it and she always described it in positive, even glowing terms.

Chapter 2

It was almost two years after that when I met a man that I thought Terry would find sexually interesting and attractive.

Ira Woodall was a local artist who was contributing to a community project that we had been working on and I took great interest in how Terry interacted with Ira.

Now, Ira was a few years younger that we were, had a trimmed, dark beard, and a ponytail, definitely artsy, very laid-back, something I knew Terry liked and it was obvious to me that she was attracted to him from the flirting that went on between the two of them, especially from her side.

One night, after we had had several glasses of wine, I decided to bring up Ira as someone she might be possibly interested in sexually.

“That Ira’s a cool guy, don’t you think?”

“Oh, yeah, I love his work, he’s just so good.”

“Like anything else about him?”

“What are you getting at, Stan? You mean as a man?”

“Yeah, I guess I am. Do you find him sexy?”

“I think most women would find him sexy.”

“But I’m asking you, Terry.”

“Yes, I think he’s very sexy, actually and I’m wondering why you’re asking me this?”

“Well, I was wondering if you would want to have him join us sometime?”

“You don’t mean for dinner, do you?”

“No, more like in the bedroom. Like we did with Phil Aston.”

“You really mean this, Stan? You want me to fuck Ira Woodall?”

“If you want to and you seemed to find him pretty appealing.”

“I find him very appealing, one of the sexiest men I’ve ever met.”

“So, if he wanted to fuck you, would you be willing?”

“Well, truthfully, it being Ira, I would be even more than just willing. I’ve told you he’s an enormously sexy man.”

So, I took the opportunity to talk with Ira one afternoon when we were the only ones there. After a little small talk, I just decided to come right out with it.

“Ira, I hope you don’t think I’m totally out of my skull, but my wife wants to fuck you.”

After a few seconds, he laughed and said, “I wondered if something was going on. Well, I have to ask you, Stan, what you think of this, she’s your wife.”

“Well, I know Terry kind of has the hots for you so if you’re game, so am I.”

So that night I told Terry and, at first, she was kind of upset but I told her that Ira took it very well and seemed pretty interested himself.

I set a meeting up with Ira to come to our house for a short discussion about the project and whatever else might arise. He knew, of course, exactly what I meant.

So, we met on a Friday evening and over some wine quickly settled the project’s issues and then I brought up the real reason we were together. Terry had worn a tube top and a short skirt with a pair of very brief panties underneath.

“Well, after Ira got over the surprise when I asked him if he was attracted to you, hon, he did say he was. So, I told him that we’re pretty open about things like that and if you were attracted to him, well, that was fine with me. So, I’ll leave you two to get acquainted for a bit,” and I got up and walked back to our bedroom to make it ready for later.

I arranged some candles and incense and made the bed ready, then went back down the hall to see what progress might have been made. As I came near the den, I could see that they had gotten closer on the couch with his arm up around her shoulder as they laughed and talked.

I was already getting hard just watching them and started rubbing my cock through my jeans as I continued watching.

I came back in the room and sat across from them as Terry said, “I’ve been talking with Ira about what you told him and he’s comfortable with everything if we are.”

“Well, I am, in fact, I’m pretty turned-on by it all.”

With that, Terry slid right up next to Ira and began kissing him as her hands roamed across his body. He lost no time feeling her breasts which were readily available just by pulling down her top. As I watched, my cock grew harder and harder.

As soon as her breasts were exposed, her hand went right down onto his lap and began rubbing on the bulge in his pants. Her tube top was now around her waist as he bent over and began kissing and sucking her breasts and she began tugging at his jeans. She stood up quickly, pulled down the tube top, her skirt and her panties, then pulled off his shirt as he loosened his belt, leaned back lifted his butt up and Terry pulled his jeans right off as he lowered his briefs to the floor.

Well, it looked like Terry chose the right guy, he had a very hard, very large cock, bigger than mine that stood right out eagerly waiting to mate with my wife.

She sat in his lap, the tip of his cock just visible between her legs as she kissed him and he fondled her breasts. She was scooting her hips around as I fumbled around trying to get my jeans open to release my poor imprisoned cock which I did get out to begin stroking as I watched them.

She lifted herself up and turned facing him on the couch and reached down to guide him inside her as she lowered herself down on his lap and began fucking him right in front of me.

“Oh, you feel so good, mmm.”

Terry was certainly turned-on, she was fucking him for all she’s worth and seemed totally oblivious that I was even in the room.

“Oh, god, your cock is so good, Ira, mmm, oh, I want to just fuck you and fuck you and fuck you,” she screamed out as she bounced up and down on him as he arched up into her.

His hands were on her boobs as she fucked him and he could hardly keep them there as she bucked up and down on him going as fast as she could.

“Mmm, mmm, oh, make me cum, Ira, make me cum, oh, your cock is so good, mmm, oh, cum, cum, mmm,” she moaned as she went up and down on his cock. I sat across watching, my cock in my hand, pleasuring myself as my wife fucked herself wild on the sofa.

“Terry, oh, you’re making me cum, Terry, UUH, UUH, UUH, un, un, mmm,” cried Ira as he shoved his hips up off the sofa jamming it into my wife who pushed down hard and twisted back and forth over and over, panting and gasping, “Oh, I’m cumming, oh, yeah, yeah, here it is, mmm, AAYYE, AAYYE, AAYYEE, uuuhn, uuuhn, oh, Ira, oh, oh,” and she fell over him as they kissed and kissed.

“Oh, Ira, that was wonderful. Oh, I love your cock, you really fill me up,” she said this as she was still sitting on him, his cock still up inside her as she continued to twist back and forth. I knew exactly what that felt like as Terry had done the same thing to me many times in the past.

She was kissing him all over his face as she squirmed over him keeping their fuck alive.

“Why don’t we take it in the bedroom where you two can be more comfortable,” I suggested. It must have been just the right thing to say as Terry pulled up off Ira’s cock and led him by the hand down the hall to our bedroom where I had lit candles and pulled the bedcovers down.

Terry got Ira down on the bed and immediately took his cock in her mouth as she swung her leg up over his head and plopped right down pushing her pussy onto his face and rubbed it all around. She was thoroughly in to sex with Ira, totally consumed by her heat for this new guy.

I sat in a wing-backed arm chair watching them orally pleasure each other as I slowly rubbed my cock back and forth. It was such a turn-on to watch my wife from across the room, I’ve been the man underneath her so many times when she was sucking me, now I get to see her pleasuring someone new.

And, Ira was pulling her labia open and tonguing up into her as she wiggled her butt back and forth just enjoying his tonguing as I know she does mine.

Terry was moaning now with a mouthful of cock and I could tell that she was really getting off on Ira’s tongue the way she was moving her pussy over his face.

I got up and walked over to the bed stroking myself the whole time as Terry began groaning as I saw her orgasm begin. I leaned back and jacked myself faster as spurts of my cum rained down on Terry’s butt and back. She looked sideways at me, then back down as she continued sucking Ira, her new lover, who was still licking around on her wet, happy pussy. She was pleasuring him like they had been together for years, comfortable, open, she sucked him as wonderfully as I knew she could do, after all, she’d done me many times.

Then, she cummed and pushed her pussy down on him, rubbing her wet juices all over his face. My face has been there so many times, I knew just how Ira was being swamped by pussy right now, Terry just loved having her pussy eaten and she always had wild orgasms from oral.

Terry was sucking him as only she can do. My wife gives the best head I’ve ever had, she’s a natural at sucking cock. She’s got Ira moaning and writhing and I know he’s not going to last much longer. I’ve been there many times myself.

Then, Terry raised up and began to turn around as she said to Ira, “God, you’ve got to fuck me, I just want you to fuck me, Ira,” And she flopped down on the bed, legs splayed wide as he got up over her, between her legs, his cock swollen and ready as he pushed it up into her as she pulled his hips hard into her.

“Mmm, fuck me, Ira, fuck me, fuck me,” she wailed as he began fucking her fast and hard. I’ve had her when she’s like this and, believe me, she doesn’t want to be made love to, she wants to be fucked and fucked hard and fast.

I got up behind them to watch him penetrate her over and over, his cock gleaming with her juice, he was pulling almost all the way out, then plunging down into her, then back out and in again.

He was grunting as he went at her and as she lifted her legs high, she cried out, “Faster, Ira, faster, oh, fuck me faster, make me cum,” and she was twisting her hips around as he plunged over and over.

Then, as he was raising back up, his cock came out and I watched her frantically reaching down trying to guide him back inside to resume their fucking. As this is all happening, I’m stroking my cock and I can tell that I’m getting really near cumming again so I slack off just a bit as I watch Ira’s cock gliding in and out of my wife’s delirious pussy.

Then, Terry just ups and pushes Ira off and over and mounts his cock and starts fucking him more frantically that I have ever seen her. She was just crazed with sex as she pumped up and down, raising up until he almost fell out of her, then plunging down hard and fast and twisting her hips back and forth, just grinding his cock up into her.

“UUH, UUH, UUH, UUH, uh, uh, oh, oh, mmm, mmm, oh, Ira, mmm, that was so good, mmm,” and she fucks him up and down a few more times, then she slides up off his cock and gets down between his legs to begin sucking him.

With Terry’s butt up in the air, her swollen, juice-drenched pussy lips so inviting, I get up behind her and shove into her and begin fucking her hard. As I push into her, Terry lets out a groan and Ira raises up to see what was happening and smiled as I began fucking her as she sucked him.

It’s all I can take at that point as I began pumping her pussy full of cum as I hear Ira groan and begin cumming in her mouth as she sucked him on and on.

I was still pretty hard and kept fucking her until Ira got up and I saw he was even harder than I was. I pulled out of Terry and he got up behind her, shoved in and went to town. Her head was down on the bed, her puss up in the air wiggling around as he took these long strokes all the way in and out of her making a ‘gooshing’ sound as he went.

I was slowly stroking again as Ira reared back and cummed her full, then collapsed down over her, his cock still traveling in and out of her as she lay there happily moaning.

“Mmm, mmm, oh, that was so good, oh, Ira, just keep fucking me, okay? Feels good. Mmm, mmm.”

Finally, Ira pulled out of her and we all fell in a pile and fell sound asleep.

The next thing I knew, I woke to see Terry up kneeling over Ira sucking his cock as he slid two fingers in and out of her wet pussy. I turned and watched them for a while as I stroked myself and as Ira began to moan, Terry raised up off his cock, smiled at him and said, “If you want me to finish that, Ira, you’ve got to come back, hon.”

“I guess I’ll just have to do that,” he replied and got up and got dressed as he had a full day of appointments ahead of him. I stayed in bed while Terry walked him to the door. In about ten minutes, she was back in bed with me and we had the fuck of a lifetime.

We do have Ira back a couple of times a month and there’s also a new produce manager at the grocery where Terry shops that she’s been flirting with. We’ll see.

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