Sherry's Weekend of Non-Stop Fun

I was trying to remember the positions that he preferred and imagine them like that. They were probably locked in a 69 at some point with him on top so his penis would go all the way in her throat and his balls would rest on her nose. He probably put her flat and face down on the bed later, fucked her ass like that and then exploded on her back.

Two hours might sound like a short time, but it feels really long if you're waiting for your girlfriend in your car, knowing that at that very moment, she has her legs wrapped around another man's waist and is screaming his name in ecstasy. I considered going back home to relieve myself of my painful boner, but somehow I was glued to my spot.

I looked up at the hotel and wondered which window was the one to Nima's room. Perversely, I began to wonder how hot it would be if he pressed my lovely girlfriend against the window and rammed her from behind in full view of the whole city.

There were a lot of people going in and out of the hotel, but at around 12:15, I saw a group of four young men in suits hanging out by the hotel entrance. They just stayed there and looked like they were waiting for someone. I wouldn't pay any attention to them, except they were blocking my view of the entrance from my car. 12:30 came and went and there was still no sign of Sherry. Was Nima going to miss his important business lunch only so he could enjoy my girlfriend's pussy some more?

It was at 12:40 that the sharply dressed hunk finally showed up with my well-fucked girlfriend on his arm like a trophy. Sherry's dress was in place but her face and neck were flushed red and her hair was out of the neat bun and flowing messily on her shoulders. It was finally clear to me why those four men were so agitated: they were Nima's coworkers and were waiting for him to arrive.

He introduced my girlfriend to his fellows and she gave each of them a kiss on the cheek. When it was Nima's turn, the kiss was on the lips, passionate and lasted quite a bit, all while Nima was grabbing her meaty butt.

Sherry finally broke off the kiss and began descending from the stairs. As she walked towards me, I could see all five men had their stares fixed on her butt. Their looks were lecherous, dripping with lust. All of them were probably imagining the same thing: their dicks plunging in and out of my girlfriend as she bent in front of them doggy style, with that beautiful ass jiggling.

"Hi darling! Let's go home. I have so much to tell you." said Sherry as she gave me a quick kiss on the lips. The second she sat down in the car, I could smell the smell of sex, sweat and semen on her body. Nima's coworkers couldn't have missed the signs when she was greeting them at the door.

I wonder how he had introduced her to his friends. His friend or his fuckbuddy? An ex-girlfriend or maybe even an escort? Or maybe he'd told them she was some clueless husband's cheating wife, or a helpless cuckold's slutty girlfriend. I'd never know. 


Saturday Afternoon

On our way home, we stopped at a cozy patio for lunch. Sherry was a perfect fit for the flowery decoration of the cute restaurant with that wild wavy hair and flowy summer dress. The two of us must have looked like the perfect picture of a happy, loving couple to everyone around us. We really were the perfect, happy couple in love, despite the strong smell of another man's cum emanating from my girlfriend's skin that suggested otherwise.

Sherry put her feet up on my lap under the table and shared obscene details of her encounter as I massaged her soles. I was right! Nima had laid her down flat on the bed and lied flat on top of her and pumped in and out of her tight back hole.

She excused herself to the bathroom a couple of times while we were eating and when she came back she told me it was because she was leaking down there. She had managed to milk him four times in the short time they'd spent together, twice in each hole. Geez, I thought, obviously Nima wasn't going to use condoms.

"Hope you're taking your pills on time baby," I said, only half joking. "Of course, silly. I always take them on time. If I didn't, do you know how many babies we would have had by now? And by so many different dads too." Touché, I thought.

When we got home, Sherry was worn out from the lack of sleep and from getting thoroughly fucked, so she said she'd clean up and come to bed for a nap, but I stopped her. I loved it when we snuggled in our bed and she still carried the smell of another man on her. I loved holding her in my arms and looking at her innocent baby face but knowing that beneath that surface, she was an easy slut.

Sherry went quiet soon, but I couldn't fall asleep at all. All I could do was look at her body and think about all the other men who knew it as intimately as I did. I looked at the tiny scar behind her ear — the result of a childhood playground incident — and wondered how many men had kissed it as she had fallen asleep in their arms.

I thought about her two very small birthmarks — one on the sole of her left foot just below her toes, and the other a tiny little dot on the puckered rim of her asshole — and wondered about the number of men who would know the location of these birthmarks by heart. How many men knew exactly how her pussy tasted when it was wet or how her face looked when she was having an orgasm?

I was lost in these thoughts when Sherry's phone began ringing. I grabbed the phone quickly and switched it to silent because I didn't want her to wake up from her deep slumber. I looked at the screen and froze in place when I saw the name on the screen: Roman.

He was a white man of Eastern European descent in his early 40s, married to a compatriot woman with three children. He was also a personal trainer. I ignored the call until the phone stopped buzzing but then a series of texts kept pouring in. I resisted for a few seconds, but then started reading them.

Back in the day, before Sherry and I moved to this apartment building with its own gymnasium, Sherry was a member at a fitness club and Roman was her trainer. The combination of her non-stop flirting and the short, tight spandex clothes that she wore to her sessions had eventually stirred something deep inside Roman's loins.

He wasn't a particularly good shag; he was the type of old school man who wanted to get his rocks off without worrying too much about the woman's satisfaction, but there were two things about him that made him attractive to Sherry: one, knowing that she was so clearly superior to his boring wife at home, and two, that because of his job, Roman's body was the most perfect male specimen on earth.

The biggest problem with Roman, however, was his persistence. Sherry ended up being a member of that gym for only 4 months, because Roman's obsession with fucking her reached unhealthy levels by the end.

If she went to the gym 5 times a week, that meant she would have to get fucked by Roman at least 5 times a week. He just would not let her go. He mostly fucked her in his walk-in private locker at the gym, but also in his office, in his car, in our car and even in her dorm room. By the end, we decided it was best for Sherry to cut off contact and start using the university's gym instead.

Roman had not taken the news well, and had given us one more reason to leave him behind: by nearly raping Sherry when she told him she wouldn't be going to the gym anymore. She had tried to pick the best moment possible to break the news to Roman, right after sex with him in her dorm room, and yet Roman had reacted badly. Sherry had tried to console him by promising him that they could still meet up every now and then, and that he could fuck her again that night as a farewell for the time being.

Roman had taken her up on that offer, but after sliding his penis inside her slowly, he'd held her hands tight with one hand, covered her mouth with other to hide her screams and proceeded to fuck her ruthlessly. Because he had just ejaculated a few minutes earlier, this assault went for quite some time, all the while Roman hurled abuse at Sherry. He'd told her that she was a cheap whore, that she just wanted to leave Roman so she could be passed around to other men like meat, and that he would fuck her till she passed out that night.

Sherry didn't bring this up with me until the day after, and even then only because I asked her why her vagina was so sensitive and had signs of scratches and bleeding. While I insisted that she had been abused, Sherry said it was her own choice to be fucked like that as she had suggested sex.

I let her have the final word, but I felt unhappy about it. It was one thing for strange men to grope her or grind on her in clubs without permission — she always craved that kind of attention — but another thing for a man to rough her up like that. The former turned me on immensely, the latter made me feel uneasy.

In the three years since that event, Roman had only fucked Sherry twice, and had been on his best behaviour both times. He'd even brought her flowers and jewellery as gifts. There was nothing in his texts that suggested he would act untoward if Sherry agreed to meet him today. His messages were practically begging for her body.

"Hi my Sherry, my wife and the kids are away for a bit and I have the house empty until 7pm. I miss you so much. I miss your beautiful body. I wanna hold you and worship you and shower you with love. Please let me know if I can meet you today. You'd make me so incredibly happy. I can pick you up at 4:30 if you like."

Great! At least he was sparing me the indignity of having to drive my girlfriend to a second fuck date in one day. I wanted to respond and tell him to fuck off, but that would be breaking a sacred rule between us. We were always honest with each other and trusted each other. I let Sherry sleep for a little while more and woke her up at 3:45.

I told her about the missed call and showed her the text. "Babyboo, you're such a doll. Of course you could have answered on my behalf if you wanted to. I'm all yours love. But since you're leaving it up to me, I'll take him up on the offer. He sounds so sweet in this text I almost feel bad for him." She stretched and yawned, then looked at me with a sheepish grin and said "Plus, maybe he'll punish me for being a naughty slut and send me back to you with a bleeding vagina again."

"Hey now! What's that supposed to mean?" I protested. Part of me wished that I'd responded to the text. I always loved seeing Sherry happy and having fun, and it turned me on to no end knowing that she was getting fucked on some other man's bed while I was alone at home. After all, I'd begged her for years to do this for us; but allowing a third man between her legs in the space of 12 hours, while all I'd gotten was a blowjob, was hard to take in. Sherry winked at me and then responded to Roman's text with a short "pick me up at the community centre on Bayville," thankfully not giving him our home address, and then jumped in the shower.

I always watched avidly as Sherry got herself dolled up for her dates. There's something incredibly sexy about watching your woman stress over how she's going to look for a man other than you. She was always so considerate of their tastes, too. She made sure she was the perfect woman of their dreams.

Having already gone the distance once that day for Nima by shaving her pussy to his liking, she picked clothes that she knew would certainly get Roman's dick hard: a sports bra that exposed all her toned torso, extremely tight spandex shorts that barely covered her ass, and running shoes with ankle-length white socks. She was a vision as she stepped out the door, and looking at her from our tenth floor window as she walked across the street to the community centre, I couldn't help but stare at her ass. It looked delicious even at that distance.

A few minutes later, an SUV stopped in front of her. She looked inside the passenger side window and then bent over and talked with the driver for a few minutes. I'm not sure why it took her so long to get in but after laughing flirtatiously and wiggling her bum for a while, she finally opened the door and hopped inside.

To all the people in the community centre parking lot, it looked like a john had just picked up a hooker dressed in slutty sports shorts. How would they know that the girl who just got picked up by a man 15 years her senior is actually an educated Phd candidate with a loving boyfriend at home?

Unlike the morning, I had the luxury of being able to masturbate thinking about what my gorgeous girlfriend was doing at that moment. But why did she bring up their rough sex? Was she just teasing me because she knew I was sensitive about that, or did she really mean it? Was she hiding something from me when she said Roman had been very tender the last two times? Suddenly, I was really turned on by the idea that a man would use my girlfriend to satisfy his own urges without regard for her sexual satisfaction, like a toy to play with and then throw away. I exploded to that thought.

It worried me that Sherry had been so explicit in the parking lot though. The two of us rarely disagreed on anything and were completely on the same page when it came to the logistics of sharing her. We both agreed that the less people knew about our lifestyle, the better. She was usually extremely careful about being discreet, not showing the wrong signs in public at the wrong times, and not sharing information with the wrong people.

Although Toronto's Iranian community wasn't small, word still spread around quickly, and if our Middle Eastern families found out, all hell would break loose. Even when she went on dates in the most discreet, intimate locations, she always kept a watchful eye for familiar faces around her. So I didn't understand her openness earlier. My parents were members of that community centre. What if they happened to be in the area? Or any of our friends or neighbours? Anybody could have seen her loitering around and then getting picked up by an older man after wiggling her butt for the public.

I was deep in these thoughts and must have lost track of time as I kept staring at the spot where I had last seen Sherry. Because sure enough, I saw the SUV pull into the parking lot again. It was already 6:50. And if I thought the show she put on in the middle of the street earlier was bad, I was in for a hell of a surprise.

Roman's car was parked for at least 10 minutes in the parking lot. I couldn't see behind the semi-tinted glass from that distance, but the best I could hope for was that they were making out and not doing something more lewd in public. Finally, the door opened and Sherry's sexy legs came into view. She blew a kiss at him and began walking towards our building but after a few steps, Roman stuck his head out his window and called her. Sherry went back over, this time to his side of the car, and then began the most stressful, but sexually intoxicating few minutes of my life.

Sherry gave him a small peck on the lips first, then another one and then another one. Slowly, their lips became inseparable and the kiss became one long sensual union. Sherry raised her hands to his head and put them on either side of his face, grabbing at his neck and messing up his hair. Their tongues met and Roman brought his right hand out the window and began pawing at Sherry's ass.

As if I wasn't nervous enough about this, Roman decided that wasn't enough, he broke off the kiss, opened his door and got out. Then, he pinned Sherry against his car and tightly held her face and began shoving his tongue in her mouth again. They were passionate and reckless, oblivious to the many people who were awkwardly watching them in broad daylight.

This man's young kids were probably waiting for their dad to pick them up somewhere and here he was, manhandling my much younger girlfriend in public. It was past 7:10 when the show was finally over and Sherry walked away from his car, though not before her ass was spanked one last time by her married lover. As she walked toward the home she shared with me, there were many pairs of eyes glued to her ass. What had gotten into her, I wondered.

Saturday Night

I was sitting at the end of the long couch in our living room, my back on the armrest and my legs stretched out. Sherry was lounging in my lap, resting her back on my chest with her head on my shoulder. She had nothing on but her panties, having taken off the spandex shorts and bra off.

She insisted that Roman had been most gentlemanly in his marital bed, but still claimed that she was too sore to have sex with me that night. The cumulative effects of allowing three men of different sizes and races open her legs must have taken their toll. So instead, I was treated to a long, sensuous blowjob that had ended with my juices down her throat.

We watched TV mindlessly for some time, all the while I was slowly massaging her clitoris and vagina and kissing the top of her head and her shoulders and her cheeks. We felt so peaceful and so in love. She was scratching my thighs and touching my feet with hers.

I thought we could have an early night in and make up for the previous night's lack of sleep and then enjoy our Sunday together. I would finally get my turn to make love to my own girlfriend, in my own bed, without distractions. Sherry had strayed enough to last her a full month, let alone one weekend. But that was for normal months and normal weekends, and this weekend was anything but normal.

Sherry's cellphone beeped with a text around 10:45pm. She grabbed it from the table and I looked over her shoulder to see a number without a name attached to it. The message just read: "Hey there sexy!"

It wasn't like Sherry to hide something from me, so I was surprised to see someone who wasn't on her contacts list had texted her this. I pretended to carry on watching the TV. Sherry slid her phone open and I noticed that she had only sent one text to that number before. It simply read: "Sherry." I was intrigued. She responded with "hello there stud" and their conversation carried on from there.

"Are you having a fun Saturday night? ;)"

"Yes, just lying down here with my boyfriend. It's lovely."

"Have you recovered already?"

"Haha, yes, recovered and then some."

"Oh yeah? Do you wanna make tonight even more fun?"

"Oh god, what's that supposed to mean?"

"Just wondering if you want some chocolate."

"I love chocolate, but I can't have it this late at night."

"How come 11 wasn't too late for chocolate last time? It's the type you like, thick and juicy, with lots of cream inside."

"You're tempting me... I can't."

"I think you'll change your mind when you see it. Should I come over or do you want to come to my hotel?"

"I'm already lounging at home in my undies, so you'll have to bring me my treat if you insist."

"You've got it princess. See you soon."

I had no idea who this mystery man was, but if the big chocolate full of cream was what I thought it was then I'd be very upset. How did he have such an easy time winning over my girlfriend when I couldn't get her to turn around on the sofa and ride me? Sherry turned around to look at me and put on her cutest, most innocent puppy face with pouty lips — the face that always melts my heart — and said, "Baby, can I ask you something?" She had no idea I'd read the texts over her head.

"I thought you were sore," I responded before she could say anything. She turned red and looked away. Good, I thought; even after allowing three different men access to her most private body parts, she still has some shame left in her.

"Baby, it's just that I'm not sure if I'll ever see Trevor again. It's just a one time thing." Huh! The mystery chocolate man was Trevor then. I knew there was something romantic about the two of them together the night before. Lo and behold, their connection had been stronger than a normal one-night stand. Come to think of it, why and when had they even exchanged numbers?