First Lesson in Cuckoldry

When I was 20 I learned my first lesson in being cuckold to my girlfriend Pip. Pip was quite shy (so I thought) and sexually inexperienced having slept with only me and one time other guy. We'd been going out for months and more or less living together. Sex was ok but not great. We first met in our local pub where she was playing pool with some friends. I took an instant liking to her as she moved around the pool table. She knew I was eyeing up and after she won her game I asked if I could play her and she agreed with the wager who ever lost bought the next round. I thought it was going to be easy as I was a good player but I was completely mistaken as she cleared the table and I had to buy her drinks the rest of the evening.

When I said double or quits she laughed and said I was a loser and once again she cleared the table and I walked off embarrassed to be beaten so easily by her. But at least I got to chat her up and walk her to the taxi stand and arranged a date which lead to us becoming a regular couple.

So a several of weeks later after several dates Pip began to regularly visit my flat for sex. We always went to the local pub to drink, meet friends and play pool. Then one evening things really took a complete change in our relationship. We entered the pub, bought our usual drinks and went into the side room to watch people playing pool. There was some different guys in the room being noisy and getting drunk and one really tall guy in his 30s was dominating the pool table, as he won match after match.

I decided to put some money down on the table to play the guy and stop his run of winning matches. He looked me up and down, then at my girlfriend and winked at her as he slide his long bony fingers down his pool cue in a suggestive way which made Pip begin to giggle. I thought I'd better beat this clown before he gets too cocky. Unfortunately, I only managed to pot one ball as he finished off the black and won easily.

Then he invited Pip to play the next match and I though he's be in for a real surprise, knowing how good a pool player Pip was. She broke off and he stood behind looking at her nice round firm butt as she bent over the table. She wore a short skirt and black stockings, so he got a good view and so did all the others in the room at Pip's sweet round ass. She looked gorgeous as I also looked at her knowing she was my girl. But Pip stopped looking at me and started flirting with this tall guy as she minced around the table.

It wasn't long before Pip won the game and we all cheered but the guy wasn't deterred and said the best of three, which Pip agreed. Then he came over to me and whispered in my ear "if I win I get to fuck your girl... okay?" I was really surprised and muttered back to him: "and if you lose?" by which he replied "I'll buy you both a meal after the pubs close in a restaurant of your choosing."

I found myself nodding in agreement, thinking he had no chance of beating my girl. The second game was very close, but he won by one ball. But Pip still looked confident as she broke off for the third crucial game. She potted the first few balls, then the guy did the same until very few were left on the table until only a black ball decider. Pip walked over to me and asked me what the guy had whispered to me and I told her the wager by which she gave me a look of disgust. Then walked over to the table to take her shot at the black to win the match. Then she turned around as she bent over the table and looked at me and then totally fluffed her shot!

I knew she'd done it on purpose as she stood watching the guy pot the black and win the match and also my girlfriend. Pip walked over to the guy and put her arms around him and gave him a long sexy kiss as the others cheered and I went red in the face. I walked up to them both and told her I was going home. She said she was staying until closing time but would come back later. I went home and then nervously waited for my girlfriend's return.

Within the hour they both arrived, drunk and laughing and joking as they entered my flat. Obviously they'd been kissing and touching on the way to my place, only a short walk from the pub.

My girlfriend sat with the guy on the settee, while I put loud music on. I went to the kitchen to get some drinks and on return the guy had his hand up Pip's skirt and was fingering her, while she looked up at the ceiling, pretending it wasn't happening. Her hand on his crotch rubbing his bulge as it expanded down his thigh. He looked at me and told me to be a "good boy" and get on my knees before her and pulled off her panties while he continued fingering her clitoris.

"Wow! O fuck" my girlfriend shouted as she unzipped his jeans and exposed his cock "you weren't kidding were you Tom...you're soooo fucking HUGE!"

Tom told me to get my girlfriend wet and ready for the fucking of her life and I knelt before her cunt and began to eat her pussy as it got really quickly moist due to her arousal. She tasted so sweet like she always did when she only wanted my tongue and not my small cock which never seem to fully satisfy her lust. But I could tell she was really turned on by this guy and was ready for him when ever he was going to fuck her.

I could feel her body heat increase as Pip went down on him sucking his thick mushroom helmet filling her sweet mouth. After ten minutes of gagging on his cock Pip pushed me away and told me to stand up and pull down my pants to show my erection. I saw Tom's cock then and it was at least four inches longer than mine and had much more girth. He had so much cock volume I wondered how she was going to fit him inside her tight little pussy?

Tom looked at my little dick and let out a loud laugh, saying why did such a gorgeous girl want to stay with such a smalldick loser like me? Pip held his cock and mine in each hand and said she knew which one was going to please her the most and it wasn't mine!

He stripped off her t shirt and bra so she was totally naked and she stood up facing me. Tom sat behind her with his huge curvy cock stretched well over his hairy belly button. Slowly with his hands on her hips he pulled my girlfriend down onto his awaiting throbbing cock. My girlfriend took a lung full of air and pressed her breasts into my face. My dick was leaking precum as I saw her butt lift to meet his throbbing cock. She ordered me to suck her nipples and finger her clit as Tom began to ride her from behind at a slow but steady pace. I saw his wide grin smiling at me as she grunted and moaned, making deep erotic noises that she never ever made when having sex with me.

lt didn't take long before her first orgasm and another and another. I'd shot my load on to the floor long before he did and she turned her pretty head towards Tom and kissed him deeply and crying with pleasure as he began to shoot his load deep inside her pussy.

Tom told Pip to pull herself off his cock and I saw his cum leak out of her cunt and saw his limp cock was bigger than mine erect! Pip turned round and cuddled up to Tom on the settee as I cleaned up the cum off the carpet and settee. Tom looked at me and said he'd like to take her to the bedroom where it would be more comfortable for the rest of the night. I thought he'd go home now he'd had his way with my girlfriend but he had other ideas.

They went to the bedroom and within half an hour they were fucking again But this time it was really intense as I had to endure listening to my girlfriend being fucked stupid by a real mature stud. I knew it was only right she had a real man for the first ime in her young life and I got to see it. Yes I must admit, it made me feel incredibly humiliated at the time but also sexually excited at the same time.

After a couple of hours I decided to walk past the bedroom door and stopped to see Pip riding on top of Tom and he cheekily saw me and gave me the thumbs up. I loved the way she rode his big cock in full rhythm making her pert pink breasts wobble and bounce. I stood for ages watching them making love and my little cock got hard sticking out of my underpants. Tom called me over and told me to join them on the bed. I felt shy and awkward but got on the bed and stroked Pip's shoulders as she continued to ride Tom making little sweet yelps of pleasure.

Tom quietly asked me if I'd ever had anal sex with my girlfriend and I said no we never had. So he told me to begin to rim Pip while he had her suck his cock once again. I was surprised at my obedience to his idea but immediately got between Pip's thighs and opened up her buttocks to expose her butt hole where I inserted my tongue. She let out a heavy sexual moan and grunt. Tom told me to begin to finger her butt one digit at a time wetting my fingers with saliva.

I eventually had four finger inside as she continued to suck on his huge member. My own cock was bursting to fuck her ass but Tom told me to move away and swap places. I sort of felt sorry for my girlfriend as we exchanged places and she took my little cock in her mouth easily while Tom got ready to fill her ass with his cock. Inch by inch he entered Pip's asshole and boy did it hurt her at first but he was real gentle for the first ten minutes but so much more masterful for the following half hour. She was crying as Tom went balls deep and had her rotating her hips. I'd already cum in her mouth and sat back watching my girlfriend being pounded by a real man.

Then in one big thunderous movement the bed shook and Tom began to cum one big shot after another deeply penetrating Pip's sweaty hot body. She squealed and groaned as she must have felt his cock bursting his hot cum filling her insides to the limit. He finally completed at least a dozen huge cock making Pip's ass glisten with a mix of sweat and cum.

We all lay on the bed and shortly after fell asleep.

When I awoke an three hours later, Tom had left (never to be seen again) and Pip was asleep, totally exhausted. She slept until 10 am the next day. I asked her later if that was what she wanted. She said it was the best fuck ever. I asked Pip would she like to meet other guys like Tom in the future! Her reply was in the affirmative and she just might allow me to be her smalldick cuckold boyfriend.

But that's another story.