A Threesome I'll Forever Regret

I let him in and closed the door behind him, and he too was wearing this cologne that smelled like an absolute stud. Genny was in the kitchen getting some food together and waved over and said "hey Ash!" There wasn't a lot of chemistry coming from her, so I was feeling a bit more confident.

Asher asked me "hey do you have any glasses for this stuff?"

I asked him how he liked it, on the rocks or neat.

He responded "always neat my friend. Always neat. Trust me."

So I got three glasses out, and he poured a little liquor into each. Genny came over and we clinked and cheered and swallowed down the delicious smoky liquid. She immediately became flush and pink in the face. Knowing her tolerance is pretty low, I knew she would be feeling a bit buzzed in no time.

I was feeling a bit more relaxed too though, and began talking to Asher about the basketball game.

He mentioned he had some money riding on it, and we began making conversation about gambling and sports.

Genny came back in with a plate of cheese and salami slices, and stumbled a bit, so I could tell she was slightly tipsy. She set the tray down and stood next to us sitting on the couch.

She asked Asher if there was much traffic on the drive over here, and he mentioned there wasn't.

She speared a piece of cheese and salami on a toothpick and turned around to head back to the kitchen, but being a little discoordinated, dropped her toothpick on the floor. This also didn't seem quite coincidental, because she bent over, with her skirt slipping up, and with her butt facing Asher, put her pussy on clear display.

She turned around and pulled her skirt back down as if it was a mistake and giggled. She goes "sorry..." and Asher was like "hey no problem" as his eyes followed her back into the kitchen.

Asher started talking to me about what he and Genny had talked about, and mentioned he knew I was having some problems. He expressed his sympathy and reassured me his intentions were good, and he only wanted to be there in any support role he could. He said "hey, I can go down on her while you penetrate. I'm sure it will turn her on a lot and probably make you really hard."

I reminded him of our ground rules (that he couldn't put his penis in my wife), and he rolled his eyes and said "well, it's yours and her rules, so she won't let me put my cock inside her."

Worriedly, I said, "well the rules apply to you too, so you can't put it in her."

He rolled his eyes again, and just said "fine."

I asked him "a promise is a promise right? Do you promise? I want to hear you say 'I Promise'."

He rolled his eyes again, winked at me and said "sure."

I was a little intoxicated too, so I thought he was just being a blowhard, but was totally respectful of the rules. So I started warming up to the situation, and realize the booze had gotten the best of me too. I started advancing things way quicker than I should have, because when Genny returned, I asked her if she wanted to go into the bedroom with me and Asher.

She looked at me surprised I was so into it, and glanced over at Asher, who was raising his eyebrows interestedly. She giggled and said "sure", and he instantly leapt up and followed her into the bedroom. I had to do a double take to realize what just happened, but also realized I was the one who proposed it, and quickly followed them in there.

I was surprised to see her top fully off in the seconds it took me to get there, as Asher started putting his hands on my wife's torso.

He very visibly had an erection underneath his jeans (and a giant bulge from what I could tell). She turned around with her back to him as he slid his hands up and cupped her breasts.

She seemed SUPER turned on, like more than I feel I ever remember her being with me (except maybe when we first started dating). She arched her back and pressed her butt against his crotch and began grinding against his hard crotch bulge. Because her pussy was so wet, you could see very clear wet marks on the front of his pants.

He quickly ripped his shirt off and pulled her butt and body closer to him and started kissing her neck. She writhed like she was in pure ecstasy.

Watching this, and her flesh against his started making me a little queasy, but I took it as a queue to start getting involved myself.

She glanced over at me and winked and motioned with her finger to come over. So I did, and started kissing her passionately on the mouth while massaging her hair. She didn't seem to kiss me long though, and pulled away from both of us and stood aside and looked at both of us very sultry. She then licked her finger slowly and reached down over her skirt and put her hand up near her pussy and started rubbing. That ecstasy look returned to her eyes.

Asher looked over at me and raised his eyebrows, and when I looked down at the increasingly large bulge in his crotch, I noticed two things. One: his dick was probably significantly bigger than mine, and two: since she was wearing a short skirt with no underwear, and her pussy gets really wet whenever she is turned on, and she had been grinding against him moments ago, his jeans had a wet spot from her vaginal juices.

Let's just suffice to say there was a persistent feeling throughout the experience that I was sortof a third wheel and that should have been my red flag to stop things. But I was blinded with wanting to also fulfill my wife sexually, and was enjoying seeing her so turned on again.

I took off my shirt and began removing my belt. As I did this, Asher unbuttoned his jeans and took them off. He was wearing black briefs, which meant his dick was all the more restrained than I originally thought. She was looking into his eyes as he reached down and started massaging his dick bulge over his briefs and looking back into hers with this sly grin on his face. His erection nearly tore through his briefs as the head of his penis peeked out through the fly hole. I kid you not, the head of his penis was like the size of a golf ball.

I nervously removed my pants and underwear in one quick move, and my dick was hard as hell, and sprung out of my pants. My penis is not the biggest. I'd say probably average of the guys I knew. The head is a little smaller than a ping-pong ball, and I'm only about 4 and a half inches long. When I get hard, my penis stands straight out, perpendicular to my body.

Genny walked over to me, turned her back to me and grabbed my penis and started massaging it and jerking it. Asher, facing us directly and only a few feet away, kept rubbing his bulge, and the bulge only got larger and larger.

Genny started grinding her pussy against my swollen penis. Because she was so wet, and my penis was so hard, it slipped right into her, and she let out a moaning sigh. Her nipples were rock hard as well. I felt proud that he very quickly got to see my penis penetrating my wife, clearly an object of his desire, early on. It felt like I was the winner, the conquerer of my wife. She bent down more to let me into her from a more rear-entry position as she gawked with her mouth open at the growing bulge in Asher's briefs, and getting her face closer to his cock.

She grabbed the waistband of his briefs, and his cock sprung up out of his pants with a vengeance. As it flung out of his underwear, it bounced up and hit her directly in the face. He apparently was turned on for a while, because his dick head was covered with a significant amount of pre-cum. As she grabbed his cock with one hand, she turned back to me to giggle, and I could see this glistening spot next to her nose where the pre-cum splattered on her face. She giggled at me with this devilish look as she started rubbing her clitoris with her left hand. She grabbed his cock and started jerking it with her right hand, and since she was in front of me, blocking my view, I didn't actually get a glimpse of it until she started rubbing it around her face. And that's when I saw it. It had to be at least 8 inches long and almost twice as thick as mine. And unlike mine when it's erect, his pointed skyward. It was better in every way.

It's like once she saw that, she knew she had to have him, and my feelings of jealousy started to return. I felt so inadequate knowing I was less than half his size.

Now I know what you're thinking. If I was feeling so jealous, why didn't I stop it? I still to this day don't know. I guess I was turned on and wanted my wife to feel pleasured sexually, and believed our ground rules prevented what would definitely a barrier that once crossed, could never turn back.

I couldn't escape the jealousy. Although I was the one with my penis inside Genny, I could feel my penis starting to respond to the jealousy as well, and become soft again. It very quickly slipped out of my wife. She felt it too, and quickly glanced back at me as if to say "are you fucking serious?" and rolled her eyes.

She quickly turned her attention back to his magnificent penis and kneeled down fully and put it inside her mouth. She hardly ever sucks my dick.

He closed his eyes and put his head back and appeared to be enjoying the sensation of my wife's amazing suck job. I would be mortified if he saw my penis becoming soft, so I quickly knelt down behind her, out of view of him, and tried to stimulate it back to life.

He almost seemed to lose attention of me entirely because he put his hands under her arms, and lifted her up. They turned and she flopped onto the edge of the bed as he stood closer and pushed her legs apart. She laid back and spread her legs as he aimed the head of his cock to thrust directly and deep into her pussy. I nearly freaked out and lost my shit because it was like she was posing for him to go inside her.

But she glanced at me and realized I was watching, saw the look on my face, and put her arm down and sat up, as he nestled closer to her. He also knew the ground rules, so he stood up against her as she went back to grabbing his dick and putting it in her mouth. She furiously started blowing this guy like his dick tasted like the best thing she's ever tasted, and I couldn't take the jealousy.

I had my hand covering my limp dick, and I felt like such a loser. With her left hand, she reached down and was massaging her enlarged clitoris, rubbing her hand all over her pussy, and sliding her fingers into her vagina. Asher stood with his head back, grunting and sighing in absolute pleasure.

She moved to lay back on the bed, and he climbed up on top of her, straddling her belly, and put his cock up between her gorgeous tits, and slipped the head of his cock back inside her mouth. She continued sucking it, with this longing look in her eyes, staring into his eyes, with a look I've never seen her give me.

She was still rubbing her clitoris so I pulled her hand aside and started going down on my wife's juicy wet vulva. She began moaning heavily as she was still eating his dick. I could tell I was getting her close to orgasm, but she squeezed her legs shut and nearly suffocated me.

I started becoming turned on again. I stood up quickly, spread her legs and put my hardening penis back inside my wife. It felt so amazingly good to feel her velvet vagina wrapped around my penis, even though it wasn't fully erect. But there it was again. I started going soft. My wife put her hand on my torso with her left hand and just pushed me away. I was rejected and heartbroken. But I was determined to return and fuck my wife.

So I got up, embarrassed to be soft in this situation, and left the room so I could jerk myself and try to get hard again. For the life of me, I couldn't do it. I spent a minute, nearly two trying to get hard with no luck.

I heard them shifting around in the other room and then her moaning stopped. I'm assuming Genny was wondering where I was.

I stood there listening and heard Asher go "can I try it? Just the tip? It's no big deal, he's not going to know. Just for a second..."

Thankfully I heard Genny subsequently respond "no, it's against the rules." I was very happy to realize my wife would stay true to her commitment to me, but felt angry he was considering breaching our agreement.

But nonetheless, I was viciously jerking myself so I could re-enter the scene, but simply could not get a boner with which to satisfy my wife.

I heard him going "oh come on, just the tip, please?"

And she responded less resistantly "no... I mean, oh my god it is so big and ... AHHH... feels so... you can only rub the tip against my clitoris. ABSOLUTELY NO PENETRATION. I can't."

And he would say "come on..."

She responded even less resistantly this time, but whispering "okay... just slip it in for just a second. That won't count."

I was mortified and livid that our agreement sounded like it was being broken!

I then heard her gasp and say breathily "oh my god! OHHH MY GOD! YOURE SO BIG!" I had a sick feeling inside me that he had breached her pussy with his enormous magnificent dick, and ran around to see what was happening, my limp dick still in my hand.

And I couldn't believe what I saw. She was laying back on her back on the bed fully, he was laying over her, and her legs were wrapped around his body. The head of his penis was inside my wife's vagina, but he pulled it back out to tease her. I watched as he was rubbing his penis head up and down my wife's vulva. He positioned the tip of his enormous enlarged cock directly over my wife's closed pussy hole.

And then I saw her flex her pussy and the hole open up. Just as soon, he began to slip through the entrance of my wife's wet fertile vagina.

I was standing right there yet it's as though they were completely oblivious to my presence. It's. It like I disappeared for long, rather that my wife didn't care that this man's unprotected penis was inside of her. That his precum was coating the inside of her vaginal folds.

I wanted to say something, to shout "stop!!", but I couldn't get the words out of my mouth. I watched it slowly slip an inch deeper as she loudly moaned "OHHHHHH my god!!" He let out this breathily sigh and stopped pushing into her. He began withdrawing and pulled his penis out entirely. Perhaps it was a heat of the moment breach.

I assumed this because once he took it out, he reached down, and grabbed his penis, and rubbed its bulbous head around her labia, back and forth over her swollen clitoris, and up and down her juicy folds. But then again, I saw him position the head of his penis directly over her hole and tease her.

He said "but I can't this time."

She just responded with this breathy sigh of disappointment, which really hurt me. I then saw her reach down and grab his dick, and position it back over the entrance of her fertile pussy as she squeezed her legs around his back and began to slowly guide the head of his penis into her vagina again. She squeezed him closer to him with the legs she had wrapped around his body as he started disappearing deeper and deeper into her. First a half inch, then a whole inch, then two inches. She was pulling him even deeper, when he pulled back and withdrew all of his penis except for a little of the head. I could see the back of that bulbous cockhead glistening with her vaginal juices, and still planted firmly inside her love canal. If for some reason he were to come right then, it would squirt right into her fertile vagina.

He said "but I can't! We're not supposed to." She seemed to ponder it briefly and breathily said to him "but I don't care." With that, she squeezed her legs around his body and thrust him back into her. This time he disappeared more quickly. I watched as his entire penis slowly disappeared into her inch by inch. I was in shock as I couldn't believe what was happening. He kept pushing in until he had about a couple inches before his balls. And then I thought I heard her whisper in his ear "I want your cum deep inside me", but I could have well hallucinated it given how distraught I was feeling. He pushed in the final length as his balls rested against her pussy and his precum-oozing cock head pressing against her fertile cervix.

He started pulling out again, but she grabbed him with her legs and thrust him entirely balls deep again. At that point I lost it.

I finally shouted "THAT'S AGAINST OUR RULES!!" He quickly pulled his penis out and looked back at me horrified, while she looked over at me and dismissively said "it's okay... he was just trying me out. I respect our rules. It's not like he was about to cum or anything" and rolled her eyes.

His dick was so hard, and his balls were pulled super-tight against his body, which I know means he's really turned on and probably close to orgasm with enough stimulation. So in the heat of the moment, I did something I will regret for the rest of my life.

Instead of kicking him out there and confronting my wife about her transgression, I for some reason said "okay... but let me get a condom first." I quickly darted back out of our bedroom and went to the bathroom where I had a stash of condoms from several years ago before she went on birth control. They weren't in the drawer I looked in initially, so I had to find them in the back of our bathroom pantry/cabinet. As I was looking for them, I heard her start breathing heavily and moaning a little bit. I hopefully assumed he was going down on her, and yet at the same time, my penis was going soft again. I wanted to go back in there hard, so before turning the corner to go back into the bedroom, I started jerking myself to get hard again.

I then heard him start to moan breathily and grunt. My stomach dropped when I realized he may not have been just going down on her. I immediately went around the corner and saw him with his almost orgasming cock deep inside my wife, BALLS deep. He was doing these short strokes, but again, with his dick head deep inside my wife, which meant like 80-100% of his penis was deep inside her, and his head probably right against her cervix.

I exclaimed "what the FUCK! I said I was going to grab a condom!" I don't know how the fuck she didn't know I meant get a condom for HIM to wear, because she says "OH! FOR HIM!"

She kept writhing around in ecstasy, throwing her head back in pleasure. As she did this, she was fondling his balls and taunting him "yeah, fill me!" He turned around and looked at me and goes "oh shit! Sorry! It's too late! I'm cumming!" and at that moment, I could see the orgasm explode within his head. His whole body tightened up.

My stomach dropped and panic was setting in, as I realized he was probably ejaculating directly onto my wife's fertile cervix. And what fucking PISSES me off is that he didn't pull out right away! He knew she was fertile!

I could see his dick and balls begin pulsing like three or four times as he shot his milky jets of semen all over the inside of my wife's fertile vagina. He then withdrew his already ejaculating penis which squirted a big load right on her open vaginal hole, up onto her vulva and eventually more on her belly - but only a few drops, confirming that the majority of his load was deposited within my wife. Within her sacred sperm sleeve, to which only I had the right to access!

I couldn't believe I inadvertently cuckolded myself and nearly wanted to vomit.

She grabbed his dick and jerked the rest of him off, with this sultry absolutely intoxicated look on her face.

He was close to the end of his orgasm as he was panting "I don't think... I didn't... I didn't get it inside her. I didn't..." There was a few drops of semen on her belly, and her still writhing in ecstasy, reached down and put her hand in it, and rubbed it up against her chest, massaging her breasts, and rubbing it all over herself. She reached down To her pussy and scooped some up and dripped it on her face and in her mouth and on her nose. She took this deep breath through her nose, with the semen all over it and was like "MMMMMM..."