Pizza Baseball And A Bet

This is another story about experiences with Jill, my first long term girlfriend and sexual partner. They are based on true events except that they are revised into a much more positive, pleasurable outcome. If we'd known then how to have a relationship good enough to do the things we could have, then maybe things could have turned out better.

***

Jill and Jenny

Jill and I were going through a rough patch. We had been together for a few years but it seemed we had different views of the future. She wanted to get married soon but I wasn't ready. She thought that seeing other people was the way to figure out if we had something good enough to wait for, or maybe it would help me get ready.

Jenny, Jill's sexually enthusiastic cousin, was in for a visit. (The same Jenny from "What Might Have Been") The two of them would get out at night after their family obligations. On the Sunday Jenny was leaving, Jill invited me to come over that night. She had things to talk about. This sounded bad.

When I arrived, she was dressed in very short denim shorts and a white gauze top that buttoned up. I could see she wasn't wearing a bra. I was not expecting that. It had been a while since we'd had sex, so I was happy for the show, whatever the reason. I reckoned that she had been out with Jenny, which could mean most anything.

She told me she had some explaining to do. She continued, "When we broke up, I planned to have sex with lots of guys. I wanted to have some fun, but I also wanted to hurt you and make you jealous. After talking to Jenny and thinking about it for a while, I decided I shouldn't use sex to hurt you when I could use it to bring us closer. It didn't make sense to do something to hurt you that I wouldn't do to make you happy.

So first, I'm going to do you any time you want it. I know we're not over all our issues yet, but I'll probably make you give it to me even if you don't want it. I hope you don't mind. It's OK though; I'll take some of the responsibility for making sure you want it.

Next, I'm going to tell you a story. This story is either completely true or completely untrue. There is no middle ground. There are a couple of conditions, (1) I'm not going to tell you which it is, true or untrue, and (2) I'll only tell you during sexual activity. Once you come, we have to stop until the sex begins again. Any type of activity is ok, and I'll do a lot of the work since I'm telling the story. I might even have a few new tricks to try on you."

As she spoke, she walked around the room and kicked off her shoes. She continued talking as she slowly unbuttoned her top to the point where only one button remained.

"For two nights in a row, Jenny and I had been talking to a couple of guys at the pizza hang out. One was the regional manager and the other was the local guy. Jenny mostly flirted with Dave, the regional guy, while the other one, Steve, showed me lots of attention. Sometimes though, Dave would get very close to me if Steve and Jenny were distracted."

The restaurant was located near our school's sports rival. Steve grew up there and was a graduate of that school.

Jill continued, "We talked about the baseball game between our two schools, which was scheduled for the following afternoon. After a good bit of trash talking, we arranged a bet. If our team won, we would get free food for a month. If theirs won, Jenny and I would have to give Dave and Steve our bras. And, we had to let them take the bras off of us.

We were state champions the previous year, so it seemed like a safe bet. But, you might remember, our team lost. At first we said we wouldn't go back to the restaurant that night, but we came up with another plan instead. We really didn't want to give them our bras, so we wouldn't even wear them. We couldn't give them what we didn't have."

"Yeah, that will teach them a lesson," I muttered quietly. Jill didn't break her concentration, even as she took off her shirt. But as she spoke she undressed me and pushed me onto the couch. She kneeled on the floor between my legs.

"Jenny and I both wore gauze tops and jean shorts. In the low lights inside, it wasn't obvious but with bright light, you could see right through our tops. We didn't care because we would probably never see those guys again. Jenny was leaving town and Dave was moving on soon to his new work assignment. Steve had a regular girlfriend.

When we arrived, Dave told us we had to pay up. Jenny told the two of them that the joke was on them, we didn't even have bras to give them. Dave said, oh no, a deal is a deal. So we would have to go to Steve's house with them and prove that we had no bra to give them. Jenny pulled me along as she stepped into the bright light of the cash register area so they could see very clearly through our tops. I could feel them both staring at me. But they said they couldn't see anything, so that was not good enough. Without even asking me, Jenny said we would go with them to make good on our bet, but that was all.

It wasn't long until the restaurant closed. Dave rode with Jenny while Steve pulled me toward his car. I got into the passenger side. While he was getting in the driver's side, I unbuttoned all but one of my buttons. I wanted to prove to him that there was no bra to give him. Maybe I could keep this short.

We hit a couple of stop lights. Each time, he leaned over and kissed me while he stuck his hand into the shirt and cupped my bare boobs. I was very nervous but excited. I thought that should be the end of our little game. It was fun but now it was time to move on. But his touch made my nipples stand out. I was sort of embarrassed. Maybe tonight was going to last longer than I thought. I was both excited and apprehensive. Maybe that excitement was what I wanted after all."

Jill stroked my dick and occasionally brought it into her mouth and rubbed her tongue all around the head. She gently held my balls as she worked.

"Steve's house was only a mile away. We arrived quicker than the time it took to answer all the questions running through my mind. At the last stop light, my last button was undone and my top was completely open.

When we got to Steve's, it was a small place. Jenny and Dave were already in the bedroom. It was separated from the living room only by a set of glass doors. The main room had two large windows with a couple of trees just outside. I thought it would be interesting if you were sitting under one of them watching us through those large windows. I made it a game for myself, pretending you were really there.

Before I even sat down Steve had my top off and I had his shirt and pants off. It's sort of a blur now. He stripped off his underwear as I watched. He wasn't bad to look at, but not terribly impressive. I pulled him toward me as I sat on the couch. I wanted to try out some blow job tricks Jenny had told me about."

Jill stood up and took off her shorts. She straddled me and guided my dick into her as she sat on me. She was so wet that I slipped in easily. I could see her in the light from the street lamp coming in through the window. She bounced as she continued the story.

"I pulled him onto the couch and moved his legs apart so I could have good access to everything. I wrapped my hand around his dick. As I pumped it, I pulled him toward my mouth. I ran my tongue around the head as I gripped firmly and pumped. I held his balls with my other hand. My fingers felt the swelling in the part behind his balls. I rubbed that part as I felt it swell even more.

I even turned sideways to the window. I imagined that would give you the best view from your seat under the tree.

Within just a few seconds, it seemed, Steve was coming in my mouth. It surprised me but I just kept pumping. He kept coming. I swallowed some of it, but I just let most of it run out. Some dripped onto my chest and ran across my hand. As strange as it sounds, I enjoyed feeling the come on my skin. As his breathing slowed, I pushed up on the swelled up part behind his balls with my fingers. More came out as he moaned. I kept pumping at a slower rate as even more seeped out.

After trying a few times to sit up, Steve fell onto the couch, almost in a coma it seemed. Now what was I going to do? I was left hanging. I was ready, but he was not. That was not my plan. I only intended to practice my blow job techniques that Jenny had told me about.

So with nothing else to do, I sneaked over to the glass door. I peeked around the edge to see Dave on top of Jenny as they bounced on the bed. He held her arms over her head as he pumped into her. She had her legs wrapped around what looked to be a nice ass. I stared.

They both moaned loudly. Steve had quietly joined me by the door. It felt sort of juvenile, but we were spying on them. Steve stood behind me rubbing my boobs and playing with my nipples. I was enjoying the attention along with the view. Just then, he pulled my arms back so my boobs stood out. He kicked the door and Dave and Jenny looked over at us. They stared at me. Dave tightened up in a loud orgasm."

I popped. I tried not to. I came and came some more. I held the boobs that were bouncing in my face. It was great but I knew that meant the story was over. And it was.

Jill brought us some drinks. She gave me a few minutes. But soon, as she sat on the couch beside me, she brought out a bottle of massage oil. She poured some in her hand and began rubbing all around my crotch. She rubbed herself with her other hand. I knew Jill was just making this stuff up, but I appreciated the effort she had obviously put into it. And besides, I was getting laid.

"Now I can continue the story," she announced.

"Steve and I sat side by side on the couch. We kissed a little as he regained his energy. He moved down to my boobs. He ran his tongue all around my nipples. He kissed and sucked and rubbed. It felt good. I discovered that I really enjoy these sensations.

Since I liked it, I thought he probably would, too. So I did the same to him. I licked and sucked his nipples just like he did to mine. We took turns kissing mouths and nipples. We didn't get in a hurry to move on."

Jill paused the story for a minute as she licked my nipples. She was rubbing her clit so I helped her with that. She came with a moan, but recovered quickly. She moved to her knees between my legs. With more oil on her hands, she clinched my dick with a very tight grip as she slowly stroked. And just like before, the other hand rubbed my balls. A two-hand/blow job is a joy. Her new techniques were a hit.

The story continued, "As Steve and I kissed, I felt another hand on my boobs. I was shocked to see Dave sitting down on my other side. I don't know if the guys had planned this, but Steve didn't seem to mind. They both moved down so they each took a boob in their mouth.

I didn't know what to do about the panic I was feeling, so I decided to just relax and enjoy. It felt great, double the pleasure. I think I had an orgasm or two just from their mouths working on my boobs, but I'm not sure. I'm sure it felt good, though.

Dave moved up to kiss me as Steve moved down between my legs. He knew what he was doing. He must have done this a lot. Dave played with my boobs as we made out. The feelings were wonderful. But probably the most fun part was imagining that while I was naked on the couch with my legs wrapped around some guy's head and another guy's hands all over my boobs, you were enjoying the show from outside.

All the sensations, attention, and thoughts got to me. I had a very strong orgasm, maybe even a few of them.

Steve asked if we were even now that he had returned the favor that I had given him. I told him no and asked if he had really brought me home just for oral sex.

He didn't answer. I told him that he had to have a condom if he was going to do me. He just pulled me down to the floor with him and put a condom in my hand. I took my time putting it on. He was definitely ready.

He turned me around on my knees with my arms on the seat of the couch. He moved around behind me and slid his dick in. He went slowly. I told him that we could be even now.

Steve held my butt but still managed to grope my boobs. Dave didn't move from his spot on the couch. I was just beside him. I rubbed his legs. Then it felt natural to grab his dick. I thought I wouldn't be in this situation very often. So I just moved over and started blowing Dave while Steve pumped into me from behind."

Jill stopped to think for a second. "Isn't that the sluttiest thing you've ever heard?"

I didn't say anything, probably because I couldn't get any words to come out.

"I think it is terribly slutty. I told myself this was a once in a lifetime chance to experiment. I'm still not sure what to think of it. I definitely enjoyed it, but nice girls don't do that, do they?"

I could barely get the response out, "Slutty is not a bad thing if it's done right." Jill went back to the story.

"It was awkward at first. I was getting lost in the focus on one or the other. Then it worked. Steve pumped me from the back, which pushed me up and down on Dave's dick. It was almost effortless on my part. And it was so erotic that it gave me a couple full body orgasms. I imagined what you would be thinking.

Dave tightened up. I could feel every pulse as he came. I swallowed some again, but I was still getting pushed up and down so there was come everywhere. I used the same techniques to milk every drop. I wanted to make sure he was completely finished off for a good while. It was a competition thing between Jenny and me.

Steve pulled out and turned me around, lying me flat on the floor. He pushed his dick into me as he pulled my legs around him. I gripped his butt as his orgasm took over his body."

Of course, I was coming as she was talking. She gave me the same treatment as Steve in the story. She kept slowly stroking, sometimes stopping to massage around and behind my balls. She would lick up the occasional drop from my dick. That must have been more of those new tricks she mentioned earlier.

Unfortunately, the story had to stop. I asked if she wanted to go out to eat. I said I wasn't assuming that we were back together but it would give us a chance to rest. That way, we could finish the story later that night. She agreed. Jill put on her same gauze top without a bra so we would have to eat at a dark place. There was a steak place in town that would work.

We found a table in a back corner in a relatively empty section. After ordering, Jill undid a couple of buttons on her top. She said she could tell me a little more, but only a little, because she was teasing me with her top unbuttoned.

"When I got up I told everyone I was going to the shower. They should continue without me. But they all followed me into the shower instead. I got in with Steve, then Dave and Jenny squeezed in also. It was a full size tub with a shower but it was tight. All the skin on skin contact was nice.

I quickly washed off. Dave and Steve took turns soaping up me, then Jenny. I gave both of them a bit of attention with some good soapy stroking. Getting squeezed between Steve's a Dave's soapy bodies was a thrill. But Jenny had been patient and this was her turn.

I got out, but the others stayed. I told Jenny that I had worn them out so they would need some time to recover. The three of them spent a few more minutes together before joining me in the living room."

Then Jill told me that was all I could have until we got back. By the time we left the restaurant, there were only a couple of buttons holding Jill's top together. Once we arrived back at her place, it had been a couple of hours. She reckoned she could finish her story.

She undressed me, then herself. She led me to the bed and laid me down. As she kissed and rubbed herself over me, she continued.

"I put my jeans and shoes on but left my top off. I knew that Jenny expected her turn with the two of them, so I thought the guys could use some visual help. And Jenny wanted exactly the same treatment I had from them. Besides, I knew you would like that from your viewpoint.

So I watched as Steve went down on her while Dave kissed and rubbed her like me before. By the time she had an orgasm, Dave was ready to go. She put him on the floor and straddled him. She then sat Steve on the edge of the couch for a blow job. As she rocked on Dave, she stroked Steve.

I enjoyed the show. I know it sounds creepy but it was fun.

Steve erupted, followed by Dave a few seconds later. They just stayed there. Neither of them moved.

After a bit, I told Jenny we had to go. We all sorted through our clothes for a while before we found the right ones. We said our goodbyes and promised to stay in touch.

I'm sure we won't. Dave will go back to his job, Jenny will return home, and Steve will go back to his girlfriend. I didn't even give him my number.

I surprised myself with the way the night turned out, especially all the things I did. I guess I intended all along to fuck Steve, but I had no idea it would lead to all that. The most surprising thing was how much fun I had. You being there, even if just in my mind, added to the fun. If I thought I would blow two guys and fuck one, all in one night, I should have felt like such a whore. But instead I feel more of a rejuvenation and awakening than anything else. I suppose it really is exciting to get out of the comfort zone sometimes."

She pulled me onto her and wrapped her legs around me. Both of us had another orgasm.

I asked if this story was real or just made up. She wouldn't say. Maybe someday she would tell me, but probably not. I didn't really believe it was true. I told her that she was never that energetic sexually.

She continued, "Based on our night, I think it brought us closer. Would you agree? That was the point of telling you. It doesn't seem like you're hurt. In fact, I'd guess that you enjoyed it quite a bit. What if the story is true? Does that change anything? Do you want it be true? Or would you rather it not be true? Would you have liked to be under that tree?"

I didn't know the answers to these questions. We were definitely closer. I asked if we could do something like that sometime. "We'll have to see," was the only answer she gave. "But I'd like you to think about those questions I asked."

Yep, I knew it was all crap, I thought. But it was fun. "I enjoyed the game," I told her. "You really had me going, but I understand now."

"I'm sure we'll talk more about it later," she replied.

That was all we said about it before I left. As I walked out past her car, I noticed a cup in the back floor. I recognized it as one of the cups they use at the pizza place. It wasn't a to-go cup, but rather, one of the regular inside cups. And, was that a bra there beside it? It looked like it, but it could have been something else. The car was locked so I couldn't be sure.

Was the story true? If it was, what could we actually do together? She said she very much enjoyed it, what would she want to do together? What would I want us to do? What should we plan?