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I’m a 50 year old man and have very fond memories of a couple I lived when when I was a young soldier stationed in Colorado. I’ve always been a very s***** person and Fort Carson was my first time away from home. One day I was in an adult bookstore and found a swingers directory for the Colorado Springs area. If you’re my generation you will remember these. They were printed on newsprint and often had black and white photos with the ads inside them.
I found an ad for a couple looking for a young man to pleasure the wife while the husband watched. On a whim I decided to call the number in the ad. Later that night I met Jack and Diane (obviously I’m not using their real names) at a restaraunt for dinner. They were in their 40’s, a little heavy but definitely not unattractive. She had wide hips and big pillowy breasts. He was about my height but a little thicker. I got a hard on just looking at her and thinking about the prospect of screwing her.
They asked me about any girlfriends or previous experience. At that point I realized I had to tell the truth, I was a virgin. I had had a girfriend in high school and we had engaged in mutual m***********, but we never actually had s**. When Jack and Diane looked at one another I thought I had killed the deal. It turned out to be quite the opposite.
We met a couple more times before they took me home. The first time Diane and I had s** while Jack videotaped it. It was pretty much straightforward s** with her giving me directions, especially on how to pleasure her orally. She was a great teacher and I was a more than willing student. It was at our third party (as we called our trysts) that I realized what I was being groomed for.
Diane picked me up in town, which was kind of unusual since Jack normally did that but I didn’t think much of it. On the way to the house Diane went on about how orally talented I was. She said I had done such a good job for her that Jack was getting jealous.
When we arrived I walked through the door and was surprised to see Jack standing in the living room stroking his hard c***. His d*** was about 6 inches and fairly thick. It wasn’t huge, but it was a textbook perfect p**** with a bulbous head and a nice shaft.
I heard the door close and when I looked back Diane was stepping out of her dress. Normally we started our parties with a couple drinks and some small talk. It was clear my teachers wanted to get down to business. Diane knelt in front of Jack and gave his hard on a couple licks. Then she looked at me, patted the floor next to her and smiled.
“Get undressed and join me,” she said.
I was nervous, but I trusted them, so I complied. I found myself at eye-level with Jacks gorgeous, hard c***. Diane was stroking it gently and whispering to me.
“It’s beautiful isn’t it?” she said. “Go ahead, taste it.”
At this point she gently squeezed this d*** and a drop of precum appeared at its tip. I leaned forward and licked the head of his c***. His precum was sticky and hot. His d*** was like a steel rod encased in silky sleeve. The head was soft and smooth and before I knew what I was doing I was working it in and out of my mouth doing my best to imitate what I had seen Diane do in our earlier meetings.
I formed my tongue under his c*** so it rode in and out of my mouth on a velvety ramp. Jack moaned and placed his had on the back of my head and gently thrust his hips back and forth f****** my virgin mouth.
Diane moved behind me and put her arms around me, pressing those big soft t*** against me. Her hands slid down my body and grasped my 19-year-old d***, which was hard as a rock by this point. She gently stroked my c*** while her husband fucked my mouth. I was almost lost in the whole thing when I felt Jack’s c*** start to jerk in my mouth. I knew what that meant.
I pulled back, but wasn’t quite quick enough, the first spurt landed in my still open mouth. The rest splashed on my face as I turned my head. Diane squealed with delight and immediately clamped her mouth over mine. Her tongue greedily searched my mouth for her husband’s s****. As we kissed we traded his sperm, mixed with our own saliva, back and forth. Finally, Diane pulled away and swallowed the sweet mixture. She then lapped and sucked up the remaining sperm from my face and chin.
Jack had fallen back in to his recliner and was rubbing his c*** which was slowly softening.
“Diane, you have something to take care of,” he said pointing at my raging hardon. My d*** was so hard it hurt.
Diane pushed me to the floor and started blowing me. It only took a few minutes and I was shooting my load into that lovely mouth. she swallowed every drop.
That night they told me they had decided to ask me to move in, if I wanted to. I lived with them for the next year and a half until I was transferred to Germany. I was basically bisexual during that time and we spent many evenings pleasing each other. I learned much from my friends and I still speak to them periodically.
Happy memories indeed.

New Confession

Mother made me take my pants down in front of her guests. She had five friends around the table and several of them had brought along their daughters who are my age and in my class at school. I had to take my pants down in front of them and then be punished while they watched and smirked.

Mother didn’t like something I said and so she ordered me to go get the belt. I hesitated thinking that she didn’t mean to punish me in front of everyone, especially the girls who were my classmates. She couldn’t, she wouldn’t. I snapped out of it when I heard Mother say, “That’s an additional ten strokes. Now do you want to go get the belt or shall I make it twenty strokes?”

I went immediately to fetch the belt. I returned and knelt before Mother as I presented the belt and the hand restraints. Mother ordered me to stand up and lower my pants and underwear. I was shocked and quivering. I fumbled to undo the snap and lower the zipper to slide out of my pants. The whole room looked on. My co.ck was already stiffening in my underwear and poking up. The girls looked at my crotch and they were amused.

I took down my underwear and my co.ck sprang up, wobbling and the girls giggled. One woman said, “Oh my.” Mother told me to take off my pants and fold them neatly and place them on the chair. I obeyed. Then she put me over her knee, restrained my hands behind me and she reached under me and grabbed my balls. Mother held me in place by my balls and then she began my whipping.

They all watched my bare bottom turning red with each stroke. They heard me gasp and plead that I’d be a good boy and Mother replied, “Yes you will be a good boy when I am done with you, won’t you?” “Yes ma’am, yes ma’am,” I moaned.

Mother told me that I had interrupted her gathering and disturbed her friends. She made me thank her for each stroke. She whipped my bare bottom fifteen times and then she added the extra ten strokes I earned for hesitating when ordered to go get the belt.

I was then allowed to stand up and my swollen co.ck was dripping clear fluid out the hole and down onto my balls. One of the women said, “That thing looks bigger now than when you started.” Mother ordered me to apologize for disturbing the gathering. I stood there with my red bottom and my red face and told everyone that I was sorry for disturbing them.

Mother then ordered me to apologize to each person. She directed me to stand in front of Mrs. Bunting and apologize to her first, which I did. Mrs. Bunting looked at my throbbing, wet co.ck and then I moved over and stood in front of Mrs. Bourne, and then the others.

Mother made me apologize to each of their daughters. One girl, Brenda reached out and grabbed my wet co.ck head and asked, “Why is this thing so wet.” Mother said, “That’s the way it gets dear.” They all laughed.

Mother told me to bend over the arm of the sofa and she handed the belt to Brenda and told her add any strokes she thought I needed. Brenda was delighted and said, “Sure, he deserves more.” Becky said, “He’ll probably get wetter.” Brenda snapped the belt across my bare bottom and I howled as a second stroke and a third stroke hit. Becky took her turn and then Jeannie took the belt. Jeannie snapped it between my legs and caught my ball sac and I jumped and squirmed as they all laughed and joked.

Then Mother had me stand in middle of the room with the tears rolling down my face and the clear liquid rolling down my purple, bulging shaft. My co.ck stayed hard for twenty minutes. It wobbled about as the girls touched it. Jennifer borrowed her mother’s camera to take a few pics, so now she and her mom have pics of me hard, sobbing with a wet erection and a red bottom.

As my co.ck started to soften, Mother asked me if I was ready to put my pa.nties on. She asked the guests if I’d look better in pink pa.nties or yellow pa.nties. They selected the yellow. I was sent to retrieve the yellow pa.nties. I returned with the frilly yellow ones with my co.ck half hard and bouncing with each step. Mother had me put on the yellow frilly pa.nties and then thank everyone for selecting them.

I was glad to have my co.ck and balls covered-up again. Jeannie soon lowered my pa.nties for another inspection. They all watched and Jeannie took a few pics. Jeannie asked about who was going to discipline me tomorrow. Mother said that Jeannie could stop by after school to do that and any other of the girls could come along too.

The next day after school I was escorted by Jeannie who told me all the way home that she was going to whip me to tears until I was begging and pleading. She did. She whipped my bare bottom harshly while Brenda watched and waited to supplement the strokes with more. Brenda was amused but Jeannie was very dedicated to inflicting as much pain as she could.

After being whipped two days in a row my bottom was sore. My balls ached too. Jennifer still has the pics and so does Jeannie. Jeannie has made many after school visits to keep me disciplined with Mother’s consent. The two of them have a friendly relation. Jeannie is very demanding, like my Mother. Jeannie really enjoys using the leather belt and she said she feels good and she feels relieved after disciplining me.

I got a whipping from Jeannie today. I’m sure she’ll walk me home tomorrow and all the way she’ll tell me how she’s going to snap my balls with the belt, make my co.ck turn purple and my bare bottom welted from her strokes.

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