An Old Fart Wins Big - Cover

An Old Fart Wins Big

Copyright© 2024 by REP

Chapter 5

We decided to address the issue of Bren sharing me with her friends. Actually, there were only two young ladies who asked Bren to share me with her.

Last night, we decided Bren should ask the two girls to have dinner with us tonight so we could talk. The plan worked, but not the way we intended. When Karen’s friends learned that two of their friends were going to talk with me tonight about taking them to bed, an additional two young women approached Bren and asked her to let me take them to bed. The result was Bren arrived home with four attractive young women following her.

Bren was going to ride home with one of the two girls, so I had left early to start dinner. Bren quickly briefed me on what happened after I left. It was a good thing I had made a large pot of chili and a sheet pan of cornbread for dinner. I liked chili and cornbread and I had planned to have some as my lunch during the next few days.

During dinner, I explained to the four young women how Bren and I had gotten ourselves into this situation. I let them know that if they still wanted me to take them to bed, I would do so. But we would have to spread the nights out for Bren and my relationship came first. We would fit them in when I had enough energy.

That was almost an insulting way to say it, but oddly enough, it made them even more adamant about finding out what it was like to be in bed with a man like me.

I just don’t understand women.

Bren remarked on the change in their attitude, and one of the women — Ann Hester — explained why she was even more eager to go to bed with me than she had been.

Ann said, “My relationships with boys in and since high school haven’t been memorable. All I would let them do, before I got to UMB, was a bit of kissing and touching. I didn’t actually have sex until last year. It was painful and the guy dumped me the next day. Since then, I’ve had sex a few times, but it was nothing like what Bren described. I want to experience lovemaking like that.

What Ken just said made it clear to me that he is devoted to you and that arouses me for some reason. However, when Ken made the offer he was your boyfriend, but now he is your husband. Having sex with your husband seems wrong to me, but I still want to be with him.”

I had watched Ann as she spoke and felt my emotions kick in for her.

Ann continued by saying, “I realize the two of you don’t really want me to join Ken in bed. So don’t worry, I won’t insist on doing that or blame you for not allowing me to have sex with him.”

The other three women were nodding their heads as Ann spoke.

I wanted to confirm what I suspected. I asked, “Did the rest of you have similar experiences?”

They all nodded and said, “Yes”.

Janet Best said, “The four of us and the rest of the girls have talked about our experiences with boys and men. There are differences between our experiences, but overall, none of us have ever had what I would consider to be a really good time in bed with a man.”

When I looked there were tears in Bren’s eyes, but they hadn’t reached her cheeks. I knew from past discussions that her experiences with boys were similar to what these four young women experienced. The main difference was she was still a virgin when she met Frank. Somehow that seemed to make the four women’s experiences worse.

I scooted over and hugged Bren. While hugging her, she whispered, “You have to take them to bed and show them what good sex is like.”

When I pull back from Bren, I could see the emotions on her face and in her eyes, so I just nodded. Her little smile let me know that she truly wanted me to bed these four women. So, I nodded in agreement.

I think I surprised the young ladies, when I said, “Bren and I agree that the four of you deserve to experience what it is like to have good sex with a skilled man. The two of us will work something out. It may require more than a month before I can spend a night with all of you.”

As the four of them left, Joyce Pittman and Janet Best gave us exceptionally intimate goodbye hugs. Hugging me like that was understandable, but the hugs they gave Bren gave me the idea that they might be bisexual. It would be very interesting if we ended up in a relationship with all four of them, and two of them were bisexual.

After they were gone, I said, “I noticed that the hugs Joyce and Diane gave you were a bit more sexual than the hugs Ann and Diane gave you. Did you get the feeling that Joyce and Janet are bisexual?”

“I never thought about something like that. Why are you asking?”

“Well ... if they are and we ended up in a relationship with one or both of them, how would you feel about having sex with a woman?”

“I don’t know. I never seriously thought about having a female lover.”

“Bren, I would not be surprised if we ended up in a long-term relationship with at least one of the four young women. You may want to give a sexual relationship with a woman some advance thought. If we ended up in a relationship with two of them, the odds are one of the two will be bi. If we let two women join our relationship, the woman not in bed with me could enjoy some time in bed with you. If we end up in a relationship with all four of them, there will be more combinations than I care to think of. For instance, if I were in bed with one of the four women, you and the other three could have a foursome.”

I could tell that Bren didn’t know what to say about my remark, so I didn’t push her. Later that night as we snuggled after our lovemaking, she said, “I have been trying to picture what it would be like to be in bed with a woman.”

I asked, “Does it disgust you?”

“No, it is just something that I never seriously considered. With the right woman, I might experiment a bit. Would that bother you?”

After yawning, I said, “No, but I’ve heard it can be arousing to watch.”

I fell asleep about then. I learned the next morning that Bren had given the idea some serious consideration until she fell asleep.


It was Friday. Yesterday, we decided to have one of the four young women join us this evening, but which one. We decided to write their names on slips of paper, and draw a slip from a hat. Bren put the slips of paper in a hat and I raised it above my head. After stirring the slips, I lowered the hat and Bren selected a slip. Ann would be joining us tomorrow night if she was still interested. Bren picked a second slip, just in case Ann decided to not join us.

We had decided on inviting the ladies selected to join me in bed to dinner on Friday evenings because if things worked out, we may want her to spend the weekend with us. Not that I would have sex with her every day, but it would give us time to get to know her.

I was still escorting Bren to and from school and classes, while using my walking stick as if my hip still bothered me. Karen’s friends had commented on how long it was taking for my hip to heal. I told them that slow healing is what they had to look forward to when they got old. I think I surprised them.

Ann followed us home when we left UMB’s campus. We talked for a while about various topics. We eventually got around to if Ann had any specific interests in what she wanted to do while in bed with me.

She said, “I don’t know much about sexual techniques. The guys usually put me on my back and fucked me until they came in me. They didn’t stay very long after that.

“Why don’t you treat me like you treat Bren?”

“All right, Ann. You and I don’t share the same feelings as Bren and I do. However, I do like you, so I can treat you in a similar manner physically with a measure of affection.”

Bren said, “I’m going to get dinner started. You two go ahead and talk.”

Anne insisted on helping Bren fix dinner. I suspected that she was nervous and didn’t want to discuss what we would soon be doing.

During dinner, Anne said, “I noticed that you don’t use your walking stick here at home. Is there a reason for that?

I replied, “When I’m moving around the campus, I occasionally get a twinge in my hip and there may not be somewhere to sit. So I need to have my walking stick available to relieve the pressure on my hip and to keep from falling down. Here at home, all I have to do is sit down somewhere.”

I had figured that someone would get around to asking me about me carrying my walking stick when it appeared like I didn’t need it. So I had created an explanation for why I carried the walking stick at UMB. All I had to do was adapt it to Ann’s question. I’m glad it flowed off my tongue smoothly without hesitation or gaps that would seem to be me trying to decide what to say next. That is a valid reason to doubt what you are being told. So is a person not meeting your eyes after you asked them a question?

Ann relaxed as we talked during dinner. When we finished dinner, Ann and I went into the living room and talked about our courses at UMB. Bren joined us a little while later, and the three of us continued that discussion.

Bren suddenly said, “I have something that needs to be done. Can you help me for a few minutes, Ann?”

They disappeared upstairs and were gone for at least five minutes. Bren came back downstairs by herself.

“I talked to Ann to make sure she was still comfortable with going to bed with you. She is waiting for you in my old bedroom. Knock lightly on the door before you go in so you don’t startle her. She said something about getting ready for you, so she may not be dressed. I like Ann, so be gentle with her and give her a good time.”

I left to go upstairs. I could hear Bren turning off the lights and locking up before going to bed.

I tapped lightly on the door and heard Ann tell me to come in. When I did, I saw that the lights had been turned off, and could tell that several scented candles had been lit. Ann was in bed with the covers pulled up to her neck. I knew she was nude beneath the covers for I could see her clothes folded and placed on a chair with her bra and panties on top.

I moved to her side of the bed, leaned over, and gave her a loving kiss. She responded. I disrobed and slid under the covers on my side of the bed. She rolled toward me, and in a whisper, she said, “I love you.”

My reaching out and caressing her face broke the ice. Ann moved toward me and kissed me. There was a lot of passion in the kiss, so I kissed back with passion. Our kiss led to full frontal contact with us hugging each other as if we were trying to merge our bodies and become one person.

I kissed my way down to Ann’s throat and then to one of her B-cup breasts. She pulled my head to her breast and whispered, “My breasts and nipples are very sensitive.”

I turned her onto her back so I could caress both breasts. She was right. I started by caressing and kissing the sides of her breast. That was enough to elicit full-throated moans. As I moved closer to her nipples, the moans became louder. I got the impression that her past lovers had not paid much attention to her breast.

When I leaned across her body and sucked her left nipple into my mouth, she orgasmed with a loud “Yes! Oh god, Yes.” I continued to caress her breasts with my mouth and hands, which evoked further moans and orgasms. Her pulling my face into her breasts made it difficult to properly caress her breasts, but she must have enjoyed the pressure on her breasts for she tried to bury my face in her chest.

It was difficult, if not impossible, to caress Ann’s breasts. So I slid my hand down and caressed her stomach. She thrust her hips up to my hand. Her moans grew louder and she grasped my hand and moved it to between her thighs. Her thighs were spread just enough to allow my hand access. She was very wet.

Moving my hand to between her thighs resulted in her releasing my head. I returned to kissing her breast and sucking her nipples as I gently inserted my middle finger into her, Ann orgasmed again, spread her thighs further, and pulled me on top of her. She is a lot stronger than she looked.

Normally, I would go down on my lover at this point and stimulate her even further, but Ann seemed to be more aroused now than Bren normally was when I slid into her. I decided to skip oral sex with Ann until later.

I grasped myself and slowly pressed myself into her. Before I expected it, I slid across her clit, U-spots, and G-spot before hitting her A-spot. Ann’s entire body spasmed and she went crazy beneath me.

As the spasms weakened, I started my swinging thrusts and reminded myself to shorten the lengths of my swings. Ann was having orgasm after orgasm when I hit the opening to her womb rather firmly.

In addition to triggering another orgasm, she started shouting “Yes, give me your baby! I want your baby!

Then she passed out. I rolled off of her, and pulled her into my arms and cuddled her.

I could hear Bren in the room with us. In a whisper, she said. “That was awesome. I heard Ann’s screams and thought I should make sure that she was okay. You definitely gave her the experience she wanted.”

In a quiet voice, I said, “We need to talk about this in the morning. I’ll stay with Ann for the rest of tonight.”

Bren returned to our bedroom. As I lay cuddling Ann, my thoughts wandered. I accepted that Ann was in love with me and wanted my baby. I examined my feelings and realized I was in love with her. I also came to realize my feelings for Janet, Joyce, and Diane were similar to the way I felt about Ann before I had sex with her. If their and my feelings were to evolve into them being in love with me, all four of them would want to join my relationship with Bren. My house had five bedrooms, but it wasn’t large enough for five adults and a child, and any possible future additions and children to our relationship.

When I had hit the opening of Ann’s womb and she started screaming that she wanted my baby, I remembered something that I had forgotten many years ago.

When Betty and I decided we didn’t want more children, it was because her doctor told her she was too old to carry a child to term and deliver it. Betty knew her doctor was right, but she still wanted more children. So before my vasectomy, Betty and I went to one of those cryogenic facilities that stored sperm and eggs. Betty wanted to be sure that there would be a large amount of viable sperm, so I made about six deposits. My sperm was still stored at that facility and from what they told Betty and me, it should still be viable.

After delivering the baby, Bren and I can have a child of our own using in vitro fertilization. That would also be true for any woman we decided to add to our relationship.

Ann woke and snuggled closer to me. It was difficult to distinguish where I stopped and Ann began. I could hear her breathing change into deep breathing and also heard her light snores. I fell asleep a short time later.


When I came out of the private bath in the morning, Ann was awake and also needed to pee. I was in bed when she came out of the bathroom and she snuggled up to me. We agreed that we were both ready for breakfast. Before we dressed and went downstairs, I told Ann that Bren and I wanted her to stay with us for the entire weekend. I also told her that after breakfast, Bren and I needed to talk privately. She was okay with both of those things.

During breakfast we talked about Ann’s experience. When we finished eating, Ann excused herself and went back upstairs to her bedroom. Bren and I went to our bedroom to talk.

Bren said, “It sounded to me like Ann is ecstatic about last night.”

“I agree. I’ve come to realize that she is in love with me, and I feel the same way about her. How do you feel about Ann?”

“About the same way as you, Ken. I think I love her, but I am not in love with her. If I spend more time with her, I might fall in love with her. I wasn’t really expecting this to happen.”

“Neither was I. It was the emotional bond we created when we had sex that made me realize I was actually in love with Ann. After you left last night, I also realized that my feelings for Janet, Joyce, and Diane are similar to what I felt for Ann before we slept together.”

“Do you think you love them?”

“I don’t know for sure, but I think I may. I recalled you talking about having sister-wives during one of our discussions. Were you serious?”

“I don’t think I was seriously thinking about adding someone to our relationship back then. But now, the thought of having a sister-wife is sort of comforting. Two or maybe three sister-wives would be okay, but I don’t know how we would deal with having four sister-wives.”

“Bren, before we decide on that, there is another matter we need to discuss. Last night I remembered that before I had my vasectomy, Betty and I deposited my sperm in a cryogenic storage facility. I think I conveniently forgot about that before Betty’s death. Ann telling me she wanted my baby prompted my memory. I think my sperm is still on deposit at that facility, and it should still be viable.”

“Are you thinking of using your sperm to get Ann pregnant?”

“Actually, my first thought was that after you deliver the baby, and the doctor says you are ready, you and I can have a baby.”

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