I Know I Shouldn’t Have Done It

I am a 33 yr old married female, average build and looks but haven’t gotten fat. I do have very nice, natural breasts that are still perky. My husband Steve is 3 years older than me and a horny guy, even more than most. He’s on active duty in the Air Force and plans to stay in until retirement. We have frequent sex and he likes to get creative and loves to roll play, particularly with me having sex with a stranger. This happened 3 years ago and I still feel guilty at times.

Our next door neighbor, James, is in his late 60s and a widower. He was invited to his brother’s retirement party, he lives a few hours out of town, but he can’t drive so he asked Steve if we would go with him and drive. We’ve known his brother, Frank, for years as well. He’s actually 2 or 3 years older than Steve. We discussed it and agreed to go with him. James said his brother had room enough for all of us so we wouldn’t need a hotel. 2 days before the trip, he called me and told me they’d just been placed on alert for some sort of training exercise. Unless it ended quickly, he wouldn’t be able to go. I knew James was going to be very disappointed since they are both widowed and have no other family. Steve and I discussed it and decided I would still take him. Steve jokingly said I should be careful because old men still get horny.

Friday came and they were still working 12 on 12 off, so James and I loaded up our car and drove to his brother’s place. The party was Saturday 12 noon at a fancy country club. We all played a round of golf before hitting the club for a few drinks. I was the only female among 8 senior citizen men.

About 5:00, everyone was ready to leave so we went back to Frank’s place. We continued drinking and eventually started playing penny anti poker. I had lost over $100 already and began to feel duped. We were also all getting quite drunk so around 7:30 I decided to take a shower to sober up a bit, and to get ready for bed so we could leave early the next day. When I got out of the shower, I put on a little white cotton short set that I often sleep in. Out of habit, I did not put on a bra or panties, but the clothes aren’t really very revealing…as long as I don’t bend over in front of anyone. Then, my boobs are visible and likely EVERYTHING if visible from behind.

I rejoined the brothers in the dining room, James had also showered and was sitting there in his boxer underwear. Frank was about to shower, but first poured us all another drink. When he was in the shower, James began flirting in earnest. He began telling me how long it has been since he’d seen a woman naked. As he poured me another stiff drink, he moved behind me and began rubbing my shoulders. I know it was so he could see my tits, but I felt a bit sorry for him so I didn’t stop him. That is until he reached down my top and grabbed my breasts! I grabbed his hands and asked what he was doing. He removed them and apologized saying how beautiful he thinks I am.

We soon continued drinking and playing poker, they continued the compliments. I was soon down over $300! And insisted on quitting. Frank offered to reduce it to $100 if I’d take my top off and continue to play. I was drunk enough so I did. By 11:00 I was again down over $350 and James offered to pay it for me if they could see me naked. I hesitated, but eventually agreed but said I was done playing. I slipped off my shorts and walked around the room for them. They asked me to be their waitress and bartender, so I made us all drinks. Before long, they were copping a feel here and there, grabbing my ass or cupping my breast. When Frank asked for a blow job, I decided to go to bed. I grabbed my clothes, kissed them good night, and went to my room tossing my clothes on a chair by the bed.

I had been asleep for a bit when I realized someone was in bed with me, it was James! He was kissing my face and had slid the cover off so I was bare from the waist up. I asked him what he thought he was doing and he asked me “Why did you get in bed naked?” I thought about it and said I didn’t know, I was just drunk. He then told me he and his brother were dying to be with a woman again and were willing to make it worth my while. I was caught off guard and didn’t respond immediately so he said “I have a time share in Cancun that I’m willing to book for you and Steve. I’ll pay for the airfare and all expenses while you’re there if you do this for us.”

As I looked at him, Frank walked over to the bed and pulled the covers off completely, then got in beside me. They both began to kiss and fondle me and the next thing I knew I was having sex with both of them. They both had very tiny penises, but the did both work and they could last a long time. The next day we drove home. Steve was there when we arrived and James went home. I told Steve all about it and he instantly took me to bed for sex. We did have a great time in Cancun…3 times!

Comments

Anonymous

by Anonymous on May 3, 2024 at 7:53 AM

I like wives like you. Did you have sex with them for the extra trips? You’re pretty expensive. I respect a woman who knows how much to charge. I guess Steve loves sloppy seconds and reclaiming you. Have you slept with anyone else and not made them pay for it?

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Anonymous

by Anonymous on May 3, 2024 at 5:18 PM

One of the 2 times I slept with both James and Frank. The other time was with Frank and one of his friends from the retirement party.

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