Second Time Cucoldry

This is a true story following the first time I spent being a cuckold with my girlfriend Pip.

Pip was so impressed with Tom's huge cock size that she enjoyed, especially after I was thoroughly humiliated by both of them and I had learned just how much a cuck I really was. She made it clear that she demanded more experiences if I was to remain her boyfriend and she expected complete compliance on my part.

We continued to have sex of a sort but she wouldn't allow me to penetrate her again due to my small dick never satisfying her. I was only allowed to use my tongue and a penis extender told me to order online. It was embarrassing to have to wear the extender over my dick and strap it around my balls. But Pip enjoyed the full length and thick girth much more than I could offer her.

She kept at me for weeks to find another situation, where she could have another guy the size of Tom or at least someone who had his sexual maturity and performance. I so wanted to please my girlfriend as she was becoming incredibly gorgeous each and every week and blossoming into a beautiful desirable woman.

At the time I was working as a gardener and removal man. I would often be employed by Terry a mature man in his late 50s who was a well to do successful property developer. One day while working at his large house Terry asked me if I wanted to come to an open party he was having at his house and bring along my girlfriend. I said okay we'd love to come the following Saturday night. Terry was married to a very attractive Thai lady called Jan who he met on his many Far East visits.

So my girlfriend and I got dressed up and went to Terry's party that Saturday night. There were dozens of guests there and lots of loud music, dancing and drinking going on. The weather was warm that evening. We were introduced to different people and Pip got lots of looks from the guys as she look lovely in a short summer dress showing, off her large breasts, sexy ass and shapely legs.

It wasn't long before she was flirting with several guys and drinking copious amounts of wine. I knew it wouldn't be long before she coped off with someone and I couldn't stop her as she'd been in a mood for weeks. Nothing I could say pleased her but the opposite as what ever L did just made her irritated. She would often call me a useless little dickhead. hat was more hurtful was Pip had told her girlfriends all about the night with Tom the stud and how I was made a smalldick cuckold. This brought much laughter amongst her friends.

So I had to get use to the idea that my girlfriend now had the upper hand on me, enough for her to call the shots and do whatever she wanted if I was to remain her boyfriend. And yes I was infatuated with her. She even considered I purchase and wear an extra small cock cage so to humiliate me further.

The party got into full swing as Terry and his lovely wife Jan told everyone to get undressed and dive into the heated swimming pool. I stood back feeling shy and awkward as several guests stripped naked and dived into the large pool, while others stood on the edge jeering at everyone who got naked. Terry came up to me and told me to strip off and I refused saying no thanks. He turned to my girlfriend Pip and put his arm around her and then accidently spilt his drink over her dress. She wasn't happy with Terry and pushed him away. Jan took Pip's hand and apologised saying she'd better go inside and clean the dress up.

I watched them both go off into the large house and then continued to drink another beer. A good half hour passed by before I decided to go into the house to see if I could find Pip. I asked if anyone knew where Jan and her might be and a woman said they'd gone in the back kitchen to the utility room. I went through to the kitchen and at the back was the utility room which had a frosted glass door. I could see through the glass two figures close to one another moving up and down.

I could make out the sound of a washing machine whirring in the background, mixed with the two women making moaning noises. I slowly pushed the utility door open a little enough to see my girlfriend only in her knickers and bra making out with Jan. They were kissing and fingering one another against the washing machine. I soon got a little stiffy as they finger fucked one another and I began to feel an urge to join in.

It was then I felt a warm hand on my shoulder. It was Terry, as he peered into the room he began laughing, saying how much he loved watching two women fucking. In a whispered voice I told Tez I didn't know that my girlfriend was ever into lesbian tricks. To which Terry replied that his wife has a way of seducing anyone she liked and obviously she liked my girlfriend.

Tez pushed me to one side and boldly walked into the utility room and in a bossy way told his wife Jan it was his turn to play with my Pip. I was astonished at his arrogance and downright cheek. More than that I was taken back by my girlfriend not resisting his advances, as he took over the position of his wife and began to rub himself in his swimming trunks against Pip's pussy.

Pip looked over at my expression and then began kissing Terry as I stood helpless at the situation I found myself in. Jan came over to me and lead me to the otherside of the room. She began to kiss me and touched my hard clitty. I could see over her shoulder that Terry had pulled down Pip's knickers and had lifted her onto the edge of the washing machine as it chugged and spun.

Jan had my clitty in her hand and squeezed it tight and called out to her husband she had found a little boy's dick to play with. Terry looked over his shoulder and told Jan to give me a blow job while he did the business with Pip. I could see his hairy shoulders and back sweating as he slide down his trunks. I couldn't believe he was going to screw my girlfriend while I was getting sucked off by a pretty Thai lady!

Jan took all of my small dick in her mouth and slowly worked her tongue around my head making me feel so horny and helpless. She was an expert at it as she made sure I didn't cum by squeezing her thumb and index finger around the base of my clitty and three fingers around my balls. I closed my eyes and all I could hear was my girlfriend moaning and the whirring and chugging sounds of the washer.

I realised that Terry had begun entering Pip's sweet young pussy and edged his way in inch by inch and by her sounds I could tell she was loving it. I opened my eyes and saw Pip was licking her lips as he held her legs and she wrapped her ankles around his hairy back. He hadn't started to thrust but stayed oddly still, while he began sucking Pip's large nipples. I always though my girlfriend had the most amazing nipples I'd ever seen, so large and veiny and beautifully suckable.

I so wanted Jan to finish me off quickly so I could leave the room and go back to the party and get drunk. It was so embarrassing for me to stand there watching my girlfriend being fucked by a guy older enough to be her Father...no more likely her Grandfather! And it was humiliating as well to have all of my little clitty in the mouth of his wife while he did the business.

Terry called out to Jan to stop what she was doing and bring me over to him. She pulled away from my clitty and stood up and taking hold my dick she pulled me over to Terry and Pip. He looked down at my hard dick and began laughing as he in turn pulled most of his cock out of Pip's cunt so I could see how thick he was in comparison to my clitty. I was amazed how much girth Terry had. He over 6 inches thick! I could see how stretched my girlfriends pussy was as only his mushroom head remained inside the opening of her very wet pussy lips.

Terry patted me on the head and said almost apologetically what a little sissy I was and my girlfriend deserved much better than me but he'd help to ease my pain by giving her the cock she so sorely needed. And so I stood with my tiny erection next to Terry as he began to thrust himself back into the welcoming cunt of my girlfriend. The spin cycle of the washing machine began at the same time as he began his first thrusts, each time thrusting deep in and out of Pip's pussy. She wriggled and moaned and scratched his shoulders at each cunt widening thrust.

Jan leaned over to Pip and began kissing her and rubbing her breasts. I stood helpless at the show and lost in thought I didn't even notice my clitty shrank as I lost the urge to cum.

When Pip began to climax it was really exciting for her I could see it in her facial expressions the sheer delight and ecstasy and Terry being very experienced was able to hold off until she came several times and then he also began to cum and cum and cum until his last one cum shot came to a shuddering stop. He pulled out his thick cock and all his hot man seed ran out like a steamy creamy stream of white cum all over the front of the washing machine. He patted me on the head again and told me to clean up my gal with tissues and when we were ready return to the party as though nothing had happened.

Terry and Jan left the room. I obediently cleaned up and asked if Pip wanted to leave and go straight home. But she ignored me, got dressed and put on her dress and she went back to the party. She danced and flirted the rest of the evening before we left the party by a taxi in the early hours.

Terry phoned me the next day and invited Pip and I to visit him again at home. But Pip refused to go with me but went on her own several times over the following weeks. Of course I was insanely jealous of Terry and wanted so badly to take his place. But Pip would hold up her little finger and tell me I was nothing but her pathetic little cuckold pinky. I had several further embarrassing episodes when I submitted as a cuckold but that's another story.