Judy
My story:
I was a tomboy when I was growing up. In elementary school, I was a long-legged, skinny thing that could outrun most boys my age and had a decent throwing arm. I was often invited into pick-up baseball games and almost always had boys hanging around me.
In high school I ran track and played softball until, in my senior year, when I gave up sports to concentrate on academics. I also grew into a woman’s body; tall and athletic looking. In college, I fast-tracked to a business degree in three years; though I did find time to lose my virginity and be a bit promiscuous.
I was taking a couple of graduate courses, thinking of an MBA when I met John. He was in his senior year and when he graduated we got married. With lots of help from our parents and massive debt, we bought an insurance business and hung out John’s newly minted CPA license. I worked part-time in the insurance office and expanded our social network.
The company flourished, due in no small part to the MILF in the office. More than a few horny husbands gave us their business hoping to get into my pants. While I never actually cheated on John, a couple of the more persistent ones got to second base in a quiet corner at a party or cookout.
When the company was established, I stayed at home, but took charge of our personal finances and started investing in our IRAs, and am doing quite well. The internet age has been great for retail investors. When our daughter was born, John was over the moon.
When John wasn’t busy with work he was totally devoted to our daughter whom he adored from the moment she popped out of me. Our sex life had never been spectacular but it suffered neglect while she was young.
When she reached her teens and wasn’t joined at the hip to daddy, I worried that I would have to entertain him by myself. That’s when he discovered internet porn. Initially, it was vanilla sex but it excited him. When we had the house to ourselves we watched together and usually ended up having mad sex after and sometimes during. In time, things progressed to swinging sites, then to cuckold videos with BBC, which turned us both on a lot.
The more we watched, the more I began to notice cuck personality traits that reminded me of my husband. He seemed content for me to manage our finances, direct our social lives, give parties, accept invites from others, decide when and where to vacation, etc.
Because of the way I matriculated, I didn’t have a college class per se, so when we got the notice for John’s twentieth reunion I urged him to attend and take me. We ran into his old ex-roommate, who resembled some of the jocks that I had dated in college. He gave off a vibe that warned me that he was dangerous.
John seemed wary of him but I was intrigued, so when he invited us for dinner, I accepted before John could decline. I recognized right away that Bob was a player and he must have seen in me a potential target. “This might get interesting,” I thought.
John and I went back to our hotel to rest before dinner. I decided to test his reaction to my talking about Bob in a positive way. It wasn’t long until his cock was at full staff. I found to my surprise that talking about Bob had made me wet and receptive. John came in my pussy after about five minutes of fucking. I was left hanging but said nothing.
My legs are my best feature so I dressed in a mid-thigh length skirt and a shear, scoop-neck blouse and strappy sandals with no stockings. Dinner was great; much wine was drunk and we all shared reminiscences of our college days. John seemed to relax around Bob. Then, when John was not looking I felt Bob’s big hand on my leg under the table; I didn’t push it away.
After dinner, we adjourned to the lounge for drinks. Things got interesting when Bob and I danced. He pulled me close enough for me to feel his hard cock pressing my belly and he explained how he satisfies married women with his big cock and that he had the hots for me.
He insisted that he saw cuckold tendencies in John and we compared notes. He was very persuasive and I really needed to see his ten-inch uncut cock. I would have taken it out and sucked it right on the dance floor if John were not sitting nearby.
Long story short, we finally convinced John that a one-time romp with Bob would be ok. It was clear that he agreed under duress and was very skittish about the whole thing. I reassured him of my love and insisted that he would be with me the entire time.
John was finally mollified, and when we were in Bob’s suite I asked John to undress me and orally get me ready, although I was already wet from dancing. Finally, Bob took over and John watched.
It was truly wonderful; Bob thrilled me with his tongue and his amazing uncircumcised cock. I could have climbed the walls in sexual abandon but restrained myself out of concern for John’s feelings. I quietly orgasmed about three times. Bob would have fucked me again that night but I said no and we left. I pleaded tiredness to John when we got back in our room.
The next morning we held a postmortem; John had several questions. The sixty-four thousand dollar one was did I want a repeat? In honesty, I had to say yes. His face dropped and his shoulders sagged. I had hurt him, but I think, not surprised him. We had no more conversations about it before the game. I thought, “Well, that’s it. I don’t want to hurt him further.” He continued to be subdued during the football game.
The big shocker was when we were leaving the stadium after the game. John turned to me; kissed me and told me to go for it. Then he walked away through the crowd. My immediate impulse was to run after him, but Bob held me back. He assured me that John would be thrilled to reclaim me later.
That night Bob turned me every way but loose. We sucked and licked each other to climaxes and then fucked to exhaustion through many orgasms. I actually dozed off after our first session with his thick cum oozing out of me. When I awoke, I had planned to go back to John but that huge cock convinced me to spend the night.
In the morning I was too sore for vaginal sex and my abdominal muscles were sore from cumming so many times. In the shower I sucked Bob to another ejaculation and swallowed it all. I loved holding his big cock and sliding the foreskin back and forth over its head before trying to get as much as possible into my mouth. But the shower floor is hard on the knees. Bob thinks that next time he should try fucking my ass. Next time?
End of Judy’s recollections
On the plane going home John was in a constant state of arousal. Judy finally placed her coat over his lap and released his cock for a handjob. She caught his jism in his handkerchief while the man on the other side of her tried not to get caught looking. After John was neatly tucked in again she turned and gave the guy her best smile, then held the cloth up to her nose for a sniff. John snorted trying to keep from laughing.
The next several days were a whirlwind of sex, fueled by Judy's recitation of her night of wanton debauchery at the hands of his nemesis, Bob. Her stories got them both so aroused that they feared their noisy orgasms would wake their daughter.
About a week after they got home a large, heavy package arrived addressed to both of them with a smaller, ornate package attached. The large box was a case of expensive wine; the small box contained a very tiny, lacy thong.
The smile on Judy’s face made John’s stomach lurch. “He knows where we live.”
