Oscar's Cuckolding

by Tony Tiger

Copyright© 2016 by Tony Tiger

Sex Story: One middle-aged man discovers to be careful what you wish for

Caution: This Sex Story contains strong sexual content, including Ma/Fa   Consensual   Reluctant   Heterosexual   Fiction   Cuckold   Humiliation   Water Sports   .

Hi, my name is Tony and I’m about to tell you a tale of tail that has unfolded over the last year or so.

We often meet at the Club de Mar Almira for drinks. I live on a sailboat in the marina in the Spanish coastal city of Almira. This day Oscar was in a foul mood. He was almost finished with his favorite Soberano brandy before he opened up to me, the best friend he had.

“I’ve thought for a while that my wife was fucking around on me but now I know for sure,” he complained.

I looked concerned, ordered another brandy for him, and asked, “How did you find this out?”

“That woman made me wear a condom last night for the first time since I had my vasectomy six months ago. We used to use them for birth control on her fertile days and I thought we were done with them. When I asked why she looked me in the eye and said she now had a lover and he didn’t want her to be messy for him. Isn’t that shitty?

“Earlier in our marriage I talked to her about fucking another guy for our fun and she wouldn’t hear of it so I quit. I wondered what had changed her mind so I asked her. That slutty new friend of hers from work, Angel something-or-other, convinced her that I wasn’t enough for her and she should try out some other guys to prove that she was right. Irene found some stud with a big dick and she likes it a lot. She made it very clear that if I want to keep her as a wife I’d better cooperate. Damn!”

I knew Angel. She was what I called a “boat-slut”. She’d fuck anybody who would take her out on their boat. Sort of a “ride for a ride”, I guess. I heard that she spent one weekend with a friend of mine and two work mates and she fucked all of them non-stop the whole time. Not for me. I like quality women.

Now for a little more background to this problem my friend was having.

I’ve known Oscar for about five years because we worked together for a while. He’s forty-three and I’m thirty-five but we hit it off. I was married when we met, no kids, and we would get together with their two young daughters or just as couples. My wife ran off with another woman and I just date now. I have no desire to buy a book when the library is nearby. Chicks like sailboats so I get enough pussy, even though I’m fussy.

Oscar’s wife Irene is the same age as Oscar but only had sex with him before marriage, unlike her husband who had a few prior experiences. Her head is adorned with reddish brown wavy hair down to her shoulders. She is 160cm (5’3”) feet and has nice exciting and full curves. She’s “ample” after two children at 69kg (152 lbs) but carries it well.

Oscar, at 177 cm (5’ 10”) and “a little” overweight at 105kg (231 lbs) has short brown hair and big brown eyes. His main concern is his genital size, below average at 11.5 cm (4.5 inches)

I am the same height as Oscar but much trimmer at 79 kilograms (175 lbs) because of my sailing and better diet. Maybe getting more sex helps too. My equipment measures 19cm (7.5 inches) long and 6 cm (2.5 inches) wide just behind the head which is not covered with a foreskin, unlike Oscar’s.

This revelation from my friend didn’t surprise me at all. My first hint that Irene was changing happened on a recent sailing outing. It was a warm day so we’d anchored and gone swimming. Here in the Mediterranean topless is very common so Irene and the daughters all swam that way. Seeing Iren’s bounteous curves uncovered and bouncing around made a bulge in my tight, brief swimsuit. She smiled when she noticed me ogling her body and her eyes went to my crotch. I need to mention that my first piece of ass was an older woman with plenty of curves too, and she made good use of them the many times she was naked with me. That is my favorite body style.

We were getting back late and the daughters and Oscar fell asleep below in the cabin. It was cooling off so Irene snuggled up to me at the wheel and put a beach towel around us. She had enjoying being topless all day so hadn’t put her upper suit back on. I put my arm around her and when my hand accidentally brushed her breast she hummed, clearly not concerned, so I reached down to cup it and she hummed louder. I felt her hand reach for my growing bulge and she stopped humming as it grew and the head protruded when she adjusted my suit to let it escape. After a few moments of touching it she said, “It is magnificent but I’d better stop before I go too far.” She went below and got dressed then back under the towel, not mentioning what had just transpired.

Two days later Irene called me and asked to have a drink on my boat after work. I offered her some sangria and let her take the lead. She opened with, “Maybe you know that I have had sex only with Oscar. That is what my Catholic parents expected. I have suspected he is a bit on the small side and my friend Angel assures me his size certainly is. The other night I was startled at how big your organ got. Is it uncomfortable for a woman?” I reassured her that no one had ever complained although a few had to adjust a little bit.

She took a big drink of wine, gathered her courage, and begged, “May I see it in the light?”

I stood up, undid my pants, and there it was, in all its limp glory.

She gasped, “My God! It is bigger soft than Oscar is fully hard. May I touch it?”

“Only if you want to see it stand up for you,” I quipped, adding, “It might like a kiss too.”

That was the encouragement she needed. Kneeling on the cabin floor she used both hands to hold and rub the shaft and cup my big hanging balls. My pride and joy filled before her eyes. Remembering the last thing I had said, she tentatively kissed and sucked it a bit too.

“The head is not covered up with skin like Oscar’s!” She exclaimed.

“That is called a foreskin which gets trimmed in a circumcision. You don’t have to roll it back.”

She tried it for herself and commented, “I always wondered what circumcision was. Does it feel any different to a woman?”

I couldn’t resist that lead, “I guess you will just have to try it to find out.” She sucked on it a little harder as I continued, “Some women say they can tell.”

I poured her another glass of wine. “It doesn’t seem fair, I am showing you my parts and I can’t see any of yours.”

“Oh, you can’t possibly think that a fat older married woman like me is sexy. I’ve seen some of your dates.” I knew she wanted to be persuaded.

“You are on board my ship and I’m the Captain so what I say must be obeyed.” Her sudden grin told me I was on the right track, giving her orders. “I want to make an inspection so remove your clothes immediately.”

She immediately complied, still standing. I walked around her and reached out to touch her nipples and buns. She shivered when I touched then. I could soon smell her arousal. I leaned over and put my hands under her full breasts, raised them up a bit, and then bit her already hard nipples. She writhed and moaned.

“Undress me completely and pleasure the Captain’s cock,” I ordered. She made quick work and her mouth got full of my organ. I hadn’t been laid for a few days so I was rising to an ejaculation. I ordered, “Get ready to taste the Captain’s seed.” Oscar said she didn’t like to give head and had never tasted his cum but she was compliant for me though, and swallowed like a champ.

She seemed disappointed as my cock wilted so I asked, “Was there something else you wanted?” She nodded and replied shyly, “I wanted to see if your big penis would fit in me.”

“Oh, in that case just keep pleasuring it with your mouth and it will soon be ready to impale you.” It didn’t take long as I thought about bouncing on her well-padded body.

As Irene laid back and opened her thighs as an invitation, I asked her, “So you are willing to let me, a friend of your husband, put my penis into your married pussy and shoot my sperm there. What if you get pregnant?”

She looked back at me and answered in a quivering voice, “I just have to try that big thing you have. I’ve never had any sperm in me but my husband’s so that will make me wicked, but I will live with that. I won’t get pregnant because this is a safe time so shoot away. It will be an excitement I’ve never had.”

Placing the point of the spear just millimeters from her moist pussy lips I commanded, “Tell me again what you want!”

“I want you to fuck me!”

Pressing firmly against the opening I ordered again, “Tell me exactly what you want!”

She was beginning to pant with desire and her voice quivered, “Stick your big cock in my cheating married pussy and fuck it and shoot your sperm where my husband does.” That was what I wanted and I began small in-and-outs that kept getting gradually deeper. She struggled to hold still as the sensations of her stretching pussy got stronger and stronger.

Finally, our pubes met and she clamped her legs around me. “Push with your hips when I go into you. Bump your clit on me.”

This was new to her and her excitement built until she had her first orgasm just from cock alone. She shook and cried out her pleasure and then laid back limp, exhausted. I kept moving inside her until I felt my pleasure hitting its peak.

“Here is the cock-juice you wanted!”, I exclaimed as the first of many hot spurts erupted inside her. She moaned with each one, saying how wicked she was. From the tone of her voice, it wasn’t a very bad “wicked”.

We rested briefly and she showered and kissed me as she left. Nothing was said about a next time but I knew there would be one. I rested up. I had a hot date tonight.

Two days later she was trying out my meat again. This time she wanted to be on top. That made her breasts a lot easier to enjoy and let her try things her way. I didn’t need to give any orders. She knew what she wanted.

A few days later we had a sail outing planned. I had invited my favorite girlfriend before Irene had come on to me. I couldn’t just un-invite her. Plus, it might keep our affair in balance. I sure didn’t want Irene’s sexual explorations to destroy her marriage.

It would be interesting to see how this newly-cheating wife would handle the situation.

The daughters were with grandparents so I could really push things. Oscar had told me over drinks that Irene was acting differently. She had refused him sex for the first time ever. He would be quite horny for what ever happened.

Irene handled Yolanda’s presence reasonably well. She could not directly compete with the taller, skinner, younger blond, so she didn’t try. I did get a glance that would have killed if it could have even though I explained the circumstances.

Captain’s orders were topless before we got underway and bottomless when we reached the anchorage where we would spend the night. THAT was going to be interesting, I knew. While sailing Oscar got up on the front deck and was chatting with Yolanda so Irene had a chance to talk to me.

“Do you fuck her?” was the first thing out of her mouth.

“Of course and for more than a year. She has other boyfriends too and is not jealous of any I have. She will fuck your husband if I ask her to”

“Absolutely NOT!”, came the quick reply showing her double standard.

Then another one from Irene, “Do you like her better than me?”

“You are very different so it is not a matter of better. Is that not true of me and Oscar?”

She looked pensive at that question, “I have not let him in me since we started out of respect for you. He is so much smaller I may not feel him anymore.”

I looked at her and gave an order, “He is your husband and lover for many years and is my friend also. I want you to sex him when you want but we will eventually make him wear a condom. But perhaps it would be exciting for you if he went in bare when it was right after I had inseminated you. Two juices in you at the same time would be hot like it has been for my girlfriends. Yolanda has fucked another boyfriend just before doing me.”

Irene said she’d think about that.

We reached our anchorage in early afternoon and swam and ate and drank. When thigs slowed down I asked Yolanda to take a nap with me. You must realize that sailboats are small and nothing is hidden so I knew they would hear and feel as we screwed. Irene and Oscar stayed in the cockpit but made no comment when we returned except for Oscar’s small erection. I’m sure he wished he could fuck her too.

We had a late dinner and watched the sunset. I fucked Yolanda again at bedtime but heard nothing from the other couple in the bow cabin. Yolanda had been drinking a lot and fell asleep after her orgasm. I went up to the cockpit and could hear Oscar snoring.

Irene came quietly, wearing a light robe. Without a word she bent over and, with hand and mouth, urged my manhood to the condition she wanted. When it was ready she turned her back to me, pulled her robe aside, and sot down in my cock. I reached around to tease her tits the way she liked while she rode me. Her fingers were fluttering on her clit.

As drained as I was, it took a while for me to cum but she got hers twice. There was no kiss as she simply got up and, without looking back, went to her berth. A short time later I felt the boat moving rhythmically. Oscar was getting seconds but unbeknownst. I’d left much less semen than usual so he probably thought it was her natural lube. Smart girl.

Irene played it cool the rest of the outing and found another time to get some of my cock too. We talked on the sail back and I told her I was pleased with her behavior. My schedule only allowed her two turns with my cock each week so she’d have to use her husband the rest of the time. She told me that her fertile period was coming up and I’d have to use condoms.

“I don’t use condoms with any one,” I emphatically replied, “You will just have to do without.” I bet that she would “take a chance”, and I was right. The subject was never mentioned again. She was now under my control so time to take the last step.

“Irene,” I said, after we had screwed one afternoon, “You must tell Oscar that you have a lover, but not who it is. Now is the time to mandate wearing a condom unless you have just been laid. I think it will excite him to fuck in another man’s cum. That is a special treat. For me it is especially erotic to feel the silky slipperiness, knowing how it got that way. For the woman it is wicked and very female to welcome different seed. Oscar will be humiliated because it is his wife being promiscuous and unfaithful. He wants that.

“You can take charge of your sex life if you are just insistent. Oscar will resist a little, of course, but he loves you and wants to please you. You could reward his compliance with an occasional blow job.”

She was nervous about this confrontation so I reassured her, “You can do it.” Then I walked through a script a couple of times. We fucked again before she left. I was meeting Oscar for drinks tomorrow after work.

That brings us back to the beginning of this story. I got him another brandy and acted sympathetic, “Oh Oscar! What a situation. I’ve run into this before with married women who came on to me. They didn’t want out of their marriages but were feeling old or under-experienced or something. It was more the reassurance and ego building than the sex itself. I don’t think Irene wants to leave you or it would be a lot different.”

He looked somewhat relieved but asked, “So what do I do? I don’t want to lose her!”

“My advice is to just be cool and supportive of her. Do what she wants and tell her you love her. I’d bet she will get over it in time and your marriage will be better. Some of the women I’ve been involved with said they learned to fuck better and their husbands liked it too.”

Oscar got agitated, “But I don’t like her fucking anybody else! It’s MY pussy!”

“WRONG! It’s hers and you need to respect that first of all. BTW, Yolanda has a couple of other guys she fucks regularly and I’ve never noticed that her pussy is any the worse for it. You didn’t even notice any change to Irene’s did you?”

He looked thoughtful, “Well, no. But I still don’t like it.”

“That’s up to you, of course. You’ve heard my advice.”

We were going sailing on a Friday night. Irene arranged to meet Oscar at the boat so she could get there early and hopefully get a cock-stuffing before the others arrived. I’m always glad to help a woman in need.

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