My Wife and My Best Friend
It was obvious that my best friend John fancied her like mad. In fact, I think most of my friends fancied her male, female, gay, or straight. John was unusually charming, kind, and flirty around her; he laughed louder at her jokes, and their cuddles always seemed to last just that little longer. Her personality shone through in social occasions with my mates. She would keep up with the boys, drinking, smoking, and arguing with the best of them.
She never showed much of her body off in company, but her blouse was always unbuttoned just enough to demonstrate that she understood what simple creatures men are. On the other hand, John’s wife was often misery in company, an obstinate vacuum of joy.
One drunken night at John’s place, while his wife was away at her parents and Claire was at home, we were having a frank discussion about sex. He confided in me that he had not had any for six months and that that had become the norm. He told me that I was lucky to have such a gorgeous wife.
I felt my heartbeat quicken.
“Do you fancy her?”
“Well, she’s a beautiful woman,” he ventured cagily.
“Yeah, but do you fancy her?” I asked.
“Let’s put it this way,” he said, “you’re a lucky man – and would I want what you have… Yes!”
I pushed it a little further.
“So, does that mean that you’ve fantasized about you and her?”
“Well … yes … maybe. Is that so bad?”
“What do you do to her in your fantasies?”
I listened intently as he explained to me in graphic detail what he wanted to do to her. Clearly, he had given this some considerable thought. He described how he wanted to seduce her, eat her, pin her down, and stare into her eyes as he filled her with his cock. He paused mid-sentence as though his brain had only just caught up with his cock.
“Shit, you wanted me to be honest, didn’t you?” he asked cautiously.
“I would love to watch you doing that to her?” I whispered slowly.
“She would never agree to that though, would she?” he ventured.
“I doubt it, but I will find out,’ I replied. “But would you really go through with it?’
“Would I fuck Claire? I hope this isn’t a trick, but yeah, I absolutely fucking would!”
John and I had got to know each other very well over the years, and we had played around quite a bit together. We figured out that we were bisexual a long time ago, and our occasional sexual adventures helped keep our universes in balance. Unfortunately, this information had been shared in a somewhat limited way with our respective wives. Although Claire had been given a much fuller picture, it had been described as teenage fumbling and discovery. Putting the guilt, cheating, and blatant dishonesty to one side, we were faithful to each other and were not physically putting our wives at risk. We also knew that full disclosure would threaten our marriages and families, but perhaps more importantly to us. We felt that they could never understand our feelings for each other and how our actions were not incompatible with married life. Successfully explaining bisexuality to a heterosexual is harder than teaching a dog to play the trumpet; also, dogs are less judgemental.
John was taller than me, four inches taller, and unlike me, he had a muscular physique. He looked like a rower, with more than a passing resemblance to David Gilmour from Pink Floyd. He laughed a little too loudly and was a bit of clumsy oaf, particularly when he drank too much whiskey, but he was a force of nature and we enjoyed each other’s company. His cock was at least three inches longer than mine and much thicker, with a pronounced curve. I had spent many hours examining that ugly brute and had felt its full power. We had fucked a few times in the past and he had always taken control; lately though we had swapped roles and I think that that pulled had him further down the rabbit hole.
I desperately wanted to see him inside Claire. The thought of it turned me on so much that I could think of little else over the next few days.
I kind of understand the cuckold’s pleasure of being humiliated by another, usually better-endowed man, but this wasn’t about humiliation for me. Instead, I was driven by the sheer excitement and joy of witnessing Claire being pleasured. I guess the thrill of another man touching her inside, where I couldn’t reach, was a part of it, but I really wanted to hear the noises that she would make. Despite herself, the noises that she couldn’t help but make when he filled her and satisfied her in a way that I could not. We had a good sex life, but I always had to prop her bottom up with a pillow to get deep enough inside her to make her groan. She had amazing orgasms, but I had only ever achieved them during foreplay, never during sex.
One drunken night, five years ago, we had played a truth or dare game, and I gave her a scenario and a choice:
“If you had to have sex with another man, would you want his cock to be bigger, smaller, or the same size as mine?”
Without a flicker, she replied, “BIGGER… I would want a bigger cock. But there’s nothing wrong with your cock, I guess. I like your cock.”
This only served to confirm what I already knew. She had obviously remembered this conversation because she had sought to reassure me many times over the next few years that I satisfied her. The truth is that my cock was adequate at four and three-quarter inches erect. Some would say I was small, but my saving grace is the thickness. Yes, I have a chode. My erect girth is five and a half inches. This thickness has saved me from being just another small dick loser. Yet, my wife’s secret confession is she wants bigger.
In many ways, I revel in having a small cock; I can go without underwear, and nothing shows, I can wear pink Calvin Klein ladies thongs, and everything is contained perfectly because my flaccid cock only measures one and a half inches – it’s tiny. It’s a huge turn-on that my tackle can fit inside something designed for a woman’s anatomy. I don’t have any crossdressing thing going on, and I look terrible in a dress. I like the soft material and the pretty color and how it makes me feel so naughty. I have no hang-ups about being on a nudist beach proudly displaying my little package; I love the fact that sometimes I could see women or couples discussing its diminutive size. I don’t lack confidence, but I do have a small cock.
The next weekend, Claire and I were a little tipsy, and I asked her about her previous boyfriends, the sex that she had enjoyed, what they did to her, what she did to them, how big they were, and any sexual fantasies she had had. Claire warmed to the fact that I was masturbating as she described what other men did to her and what they felt like inside her.
She admitted that all her previous boyfriends were bigger and that each cock felt different inside her. I sensed that she was kind in her descriptions. She began to warm to the idea of talking dirty for the first time. She revealed that she had fantasized about threesomes and more, declaring that she was a secret princess who loved the idea of all that attention.
I summoned up the courage and said that I would love to watch another man inside her, that the idea turned me on hugely.
Her eyes lit up.
“That sounds like a lot of fun. It’s a nice fantasy,” she whispered.
I tried another truth or dare scenario: “OK, so you have to fuck one of my friends, who would it be?”
I was expecting a hesitant, guarded response, but she took this question seriously and assessed it one after another.
“John,” she said. “It would have to be John.”
“Have you fantasized about sex with John before, about him being inside you?” I asked.
“I may have done,” she replied playfully.
I couldn’t get any more out of her than that. Clearly, it was a fantasy she enjoyed, and the idea turned her on. She was no fan of John’s wife either, as she had been particularly awkward the last time we were together.
“I don’t think for a second, that John would be interested in any of that,” she said. She watched the expression change on my face. “You’ve discussed this with him, haven’t you?”
“Yes, I have, and it looks like you share the same fantasy.”
We talked about boundaries, but it transpired that there weren’t really any, apart from anal sex.
I wanted to keep that to myself. I don’t know why, but I felt that he would own her if he had anal sex with her. That would mean that he would have done everything that I had done and possibly done it better than me. This made me feel panicky. I wanted to save something, something just for So. I explained to Claire that for my part, I wanted her to get off with him, to kiss, cuddle him, and for him to make love to her and cum inside her, as though they had met on a date. I wanted to see his cock inside her, pumping her, and I wanted to lick the cum out of her after they had finished.
She was keen to leave the planning there. Besides, I still don’t think that she thought that it would actually happen. She felt that I would get cold feet and that my jealousy would get in the way. Despite her reservations, she insisted a couple of times that I could pull out at any time if it did happen. As we left it, if it happened, it happened, but Claire didn’t want to feel any pressure, and she certainly didn’t want a detailed agenda.
Two weeks later, it was arranged. John was coming to stay the night. His wife was staying with her parents again. I hadn’t mentioned it again to Claire in the meantime, as she doesn’t like planning; it’s her way of retaining control. In the hours before he arrived, she spent much time preparing. She had been to the hairdresser that morning and clothes shopping. I knew that she had shaved her pussy, as she spent ages in the bathroom. Finally, she emerged from the bedroom in a new, dark blue, short denim skirt with shiny, bare white legs and a black, buttoned blouse. There was ample cleavage on display. She looked gorgeous.
Five minutes later, the doorbell rang.
“You look nice,” John said as he kissed and hugged her.
We had a few drinks and a lovely meal. There was tension in the air. Even though we had known each other for over ten years, it was awkward making this transition; it seemed really difficult to move things along. A few minutes later, he complimented her again on how good she looked. She gave him a twirl, and he hugged her. This one lasted longer, and after they had finished, he held her around the waist, and they stared into each other eyes.
“You’ve got beautiful eyes,” he said, and he kissed her on the mouth.
Their eyes were fixed on each other, and he kissed her again. This time their lips stayed together. Claire threw me a fleeting look and then returned to his eyes. My best friend moved in again, and they began kissing more passionately. He moved her body close to his, and while their bodies ground together, the kissing became deeper and more intense. He squeezed her bottom and cupped her breasts. It was clear that they were in heaven. Claire moved her hand down to touch the bulge in his trousers. She looked back into his eyes. Every few moments, they would stop kissing and stare deeply at each other before recommencing. This definitely broke the ice, and we chatted and drank some more.
By now, it was nearing midnight, and we had put up a mattress in the lounge, where John was going to sleep. While he went to the toilet, I cuddled Claire on the bed and slipped my finger past her panties, inside her soaking wet, soft, bald pussy. We exchanged a long, tension-filled look, my heart in my throat. That was the final moment, the point of no return. Then John returned. I gently pulled Claire’s legs apart and asked him whether he liked what he saw. He stared at her pink knickers, barely covering her swollen, wet pussy. Finally, he took my place, and I went to sit on the sofa.
He started kissing her again, more passionately than before. Gone was the awkwardness and hesitancy; this was the kissing of a couple who were going to make love. When Claire and I had discussed this, I said that I wanted her to give all of herself and to make love, not just fuck. I wanted her to revel in every minute of it without any guilt. She may not have fully comprehended my feelings, but she understood the pleasure that I would get from seeing her with a man with a cock far bigger than mine, a cock that could fully satisfy her.
By now, he had unbuttoned her blouse and taken off her bra. His wife was pretty and trim, with a killer arse, but she had tiny breasts, so this was a treat for him. He sucked and licked her nipples, all the time moving from her breasts to her mouth. His hands were all over her white breasts, cupping them, squeezing them, holding them, enjoying them. I was so turned on that I didn’t dare to touch myself. This was already the best sexual experience I had ever had, and it was getting better and scarier by the second. I had fantasized about him taking off her knickers; I knew that once he had pulled down her skirt, I would get to enjoy that magical moment when she lifted her bottom up to allow him to slip them off completely. It was a special kind of signal that she was giving herself to him.
Claire threw me a momentary nervous glance, then returned her gaze to him and compliantly lifted her bottom off the mattress without taking her eyes of him. He slid her knickers down to her knees and shot me one last look, a final chance to bail out, but I just smiled back. He gently slid her knickers over her ankles, sniffed them deeply and dropped them onto my seat, without acknowledging me. They were sopping wet. She moaned as he began to work his tongue into her. She began to make deep groaning noises, new noises. I was hoping to hear more, once he was inside her.
Would she be afraid to show her enjoyment in order not to humiliate me, I wondered?
He took his time and pleasured her first with short, gentle strokes of his tongue, building and building for long minutes until he worked with longer, deeper strokes, each met with a long groan or sigh. She really wanted him inside her, and he was teasing her. Then, finally, he looked at her again in the eyes and slipped off his trousers without breaking eye contact. His cock looked fit to burst in his pants, and Claire just blurted out, “It’s huge.”
She kept her eyes fixed on him and spread her legs wide apart. She didn’t reach for a pillow to prop up her bottom. This really turned me on, as I could see that she was desperate for him to be inside her. I thought she would look at me to check, just to be sure that I was ok with this, but her eyes were on him; I was no longer in her thoughts. John slipped his pants off, and his cock stood to attention. Claire was faced with this truncheon, this curved, rock-hard, nine by the six-inch beast. It certainly wouldn’t have won any beauty competitions, but it was a tool and a half. She had had to make do with something a lot smaller, a poor imitation, for so long; her eyes shone.
“Fucking hell!” she blurted out. “That’s a monster! Go gently … Please!”
He placed the head of his cock on the outside of Claire’s pussy, and they stared deeply into each other’s eyes. Claire’s eyes moved from his eyes to his cock, backward and forwards. Finally, he pushed his cock gently inside her, and she moaned hard as its bulging head disappeared inside her.
“Oh my God,” she said in a momentary panic as it disappeared beyond the halfway point inside her. “You’re inside me, and I can still see it,” she whispered, her eyes fixed on his cock.
I knew that at this point, he was already touching her where I couldn’t reach. He stopped in his tracks and held at that point. He gradually pushed a little deeper, then back to halfway, then a little deeper again. All the while, Claire’s eyes were fixed on him, her lover. Both had forgotten I was there. Claire’s moaning became deeper as he pushed inside her. He knew full well that he was touching Claire where I simply could not.
“Does he feel big?” I asked.
She looked back at me and just squeezed out a yes, before drifting back to him. He pushed inside her until only his tight, cum-filled balls were visible outside her swollen, bald pussy. Claire was moaning. She was making noises, guttural noises, animal noises that I had not heard before. He pinned both her hands above her head and started pumping her faster and faster. She was his, and he was hers, and it was beautiful. I decided to go to the bathroom, as I wanted to hear them from outside the door, and somehow, the idea of them fucking without me there was even more of a turn-on for me.
It was so hard to pee through my erection, hearing them in the next room, that it took me five minutes. I returned to hear her moaning becoming louder and louder. I had never been able to make her cum through intercourse; I had to rely on foreplay for that. Her head suddenly raised bolt upright off the pillow, and she let out a long rasping cry as she pulsed, shook, and trembled. The pulses became more and more rapid as the intensity of her orgasm built and built. She had no guilt about me watching her orgasm during sex for the first time with my best friend. As if to underline his prowess and my inadequacies, John climaxed a moment later and emptied his balls into her pussy, while she came for a second and then a third time. He remained on top of her, grinding for a few seconds more.
“Don’t pull out,” she said, “kiss me,” and they kissed passionately and longingly as she came again, harder than before.
He pulled out with a grunt and rolled over, exhausted. Claire was left trembling. Her legs were wide apart. She tried saying something, but her words were muddled. Her pussy swollen and raw, I moved in and immediately began to kiss her. Her bald pussy was red. It looked beaten and used, distinctly second hand. There was a huge amount of cum dripping out her pussy, and it was pooling inside her. I carefully licked her clean before going deeper and removing all of his seed from inside her. Out of respect, I swallowed every drop. It seemed rude not to. I then pressed a hard cock against her swollen lips. After initial resistance, my cock slipped inside her swollen lips, but I could barely feel the sides. The slippery cum still inside her made me orgasm straight away, and I kissed her passionately.
John was a machine, and after another drink, he went to cuddle her, and they started kissing again. It’s hard to explain, but this was lovers kissing each other. It was different from what had come before, and it was intoxicating to watch. John parted her legs again and began kissing her pussy.
“You look quite sore, my love,” John said to her tenderly.
Then he raised her legs in the air, like a small plaything, and ran his tongue in one long lingering stroke across the open crack of her bottom. Claire encouraged him by moaning and spread her legs even farther apart to push his tongue inside her ass. He worked his tongue steadily inside, each stroke met with a blissful groan, until Claire broke the silence.
“I want him to,” she said, staring at me without faltering. “I just want him to.”
“OK,” I blurted.
I wasn’t panicking. I was calm. I felt this great sense of peace and ease. I don’t know why, but I really wanted him to fuck her in the ass too.
I had discussed with her in detail that I didn’t want John to do this, as it would feel to me that he owned her, but somehow, what had come before, had changed everything.
“He’s afraid that you’ll own me,” she whispered to John smiling. She looked at me. “John already owns me.”
John propped up her bottom on a pillow and turned to me. “I’ve got no spit,” he said.
I leaned over and put all my spit, first in my hand and then onto her anus. In a second, I was back on my chair, watching John placing his bulging cock head against Clair’s tiny asshole. Their faces moved together, and their mouths remained interlocked as he pushed deeper and deeper inside her arse.
“I don’t think I can take it all,” she said after he edged over halfway inside her.
“You just have,” he moaned as he pushed the last part of his huge, swollen cock inside her.
She trembled and moaned and came again on his cock. This orgasm was silent, yet somehow more intense than earlier on. Their eyes remained locked.
“I’m yours,” she said to him. “Oh my God, I’m yours.”
He pulled out of her, and they kissed one last time before we all had a final drink. There was no tension left. It had all vanished in the last act. It was now four in the morning, and we could hear the birds outside. She kissed John one last time on the lips, and we went to bed together holding hands. I felt closer to my Claire than ever before, and we fell asleep silently, locked in an embrace.