Why Didn't I Just...
Chapter 35

Copyright┬ę 2006 by Openbook

Erotica Sex Story: Chapter 35 - Jimmy Gordon has spent his life drinking, smoking and making money. Now, his lifestyle has caught up with him and he has no time left. At home, drinking and feeling sorry for himself, he finds the one thing he really needs, a second chance.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Time Travel   Historical   DoOver  


We left the restaurant right after Diane gave up asking me for a repeat demonstration. She was quiet as we drove back over to the campus. It was still only about nine o'clock when I parked my car and started to get out so I could walk with Diane over to her dorm. Before I could help her, she opened her own door and hopped out.

"I'll be back in a minute, don't you leave." She took off then, heading towards her dorm room. Three minutes later, she came back into view, carrying her choir robe in her hands. She opened the passenger side again, and got back in the car, after first putting her robe on. She sat back down in the seat, turning to face towards me with one leg up on the seat.

"I'm ready."

I looked at her. Twenty four hours before, she was on her bed, bawling her eyes out over her lost love, and now she was here, ready to watch me jack off while she wore her choir gown. This girl was special. Resilience like hers needed to be appreciated. This girl had an abundance of spunk. I admired her for it.

"What are you doing?"

"What do you mean?"

"Why did you go get that robe?"

"For your reward. Isn't this what you said? You said you wanted to masturbate in the car with me sitting there watching you, and you wanted me wearing my choir robe."

"Why would I want to do it now?"

"Isn't this what you told me you wanted?"

"When I said that, it was only so I could prove to you I'm not really an angel. I know now you don't really think I'm an angel. It wouldn't be much of a reward now anyway."

"Why not?"

"Well, for one thing, I'm not really in the mood. For another, you don't really want to see me doing it. Mostly though, it's the fact I'm a little too old to be sitting in a car, getting myself off. It's not very dignified."

"All right. I just thought it was part of the deal. If you don't want to, I'll just go in the dorm."

"Good night, Diane. I enjoyed being with you today. I hope you enjoyed yourself too."

"I did. Will I be seeing you again?"

"I don't know. I like you, but you seem to still be in love with Leon. Perhaps I should let you have some time to get over him before I start taking you out."

"Is that what you are planning on? You are going to start taking me out?"

"I was hoping to."

"I'd like to go back flying again. How will you know when I'm over Leon?"

"You'll call me and tell me you are." I had written my phone number on the back of an empty envelope, I handed it to her. "Good night Diane."

"Good night, Jimmy." It was the first time she'd ever called me by my name. To me, it was a sign of her recognition of me as just another person. When I got home, I had my guardian show me a tape of what she was doing. I wanted to find out if she crying again, or, if she was doing better. She was brushing out her hair, and remembering different things about the time we'd spent together that day. While I watched, she started running her fingers lightly over the tops of her pj's, while she remembered how it had felt to have bigger breasts.

<Give her the same sized boobs as last time. Let her keep them for an hour, but if she trys to leave her room or if anyone comes near her door, turn them back to her normal size.>

Once again, it startled her, but she soon smiled and stood up, taking her top off. She was heading out of her room, to go look in the mirror in the dorm bathroom. As soon as she opened her door, the breasts were shrunk back to her normal size. She closed the door, and they returned once more. Once again, she opened up her door, and once again, her breasts disappeared. She shut the door and turned her light off. She got into bed and spent the next few minutes exploring her new endowments. She began to think about Leon, picturing the two of them making love together, her new breasts on prominent display. Apparently, her tiny breasts had been something of an impediment in their relationship. Leon preferred girls to have bigger breasts, and had never taken the trouble to keep this preference from Diane. When it became obvious to me that Diane was in the process of working herself up to an orgasm, I had my guardian stop running the tape.

It was another two weeks before I heard from Diane. In the meantime, I'd been checking in on her by watching tapes several times each day. She and Leon had one short conversation together, instigated by Diane, and taking place outside the classroom where Leon was a teaching assistant. It hadn't gone well for either of them, ending only after Diane was through screaming at him, and with her once again in tears. Her very public histrionics had made Leon extremely uncomfortable, but he was unable to leave due to his being assigned to oversee that classroom. As soon as she had fled the area, I had the guardian cause Leon to be visited again with the shits. I allowed him to make it to the restroom this time, but just barely. I instructed the guardian to let him get back to the classroom before giving him another bowel attack. I kept that up for the next hour or more, always letting him barely make it in time. I might have kept going, if the guardian hadn't warned me that Leon was becoming seriously dehydrated.

In the meantime, while I waited to see if Diane would contact me, I received another very enthusiastic letter from Connie. She told me that if I came anywhere near the Bay Area and didn't stop off to see her, she would be devastated. I wrote her back, telling her I'd be flying up on Friday, October 17th, and I'd give her a call after I was finished with my business. I told her I could stay over for the whole weekend before returning home on Monday. It would be good to spend some time with Connie again.

My mother answered the telephone when Diane called. It was a Saturday, at about nine in the morning. I was outside washing my car when she called. When my mom opened the door and called me to the telephone, I thought it was Ken, because I had been expecting him to phone me. He was working on another partnership idea he had come up with, and he had run into a little snag he was trying to find a workaround for. Ken was always good at coming up with new ideas to reduce or eliminate tax liability on investment income. Since it was the only kind of income I had, I liked to help sponsor his research. As interested as I was in what Ken was doing, I was happier to find out it was Diane calling me.

"Jimmy, this is Diane Lowery, from Chapman college?"

"I remember Diane. It's good to hear from you. I was hoping you'd call. Are you ready to go flying again?"

"Yes. I'm over Leon. I found out you were right about him all along. When can we go flying?"

"I'm washing my car right now. If you want to go up this morning, I can be over to pick you up in about two hours."

"How should I dress? Should I bring my my Choir robe?"

"I'm going to be wearing jeans and a short sleeved shirt. You should wear something comfortable, and maybe a bra a few sizes too big for you. When we get in the air, I'll fill it for you."

"I was going to ask you about whether you were going to do it again or not. I don't have any big bras. I'll just take my bra off so it doesn't get all broken like the last time. Could you make them even bigger this time?"

"I don't know whether it's a good idea to make them much bigger than the last time. You wouldn't want to be top heavy."

"I wouldn't most of the time, but when you've spent your whole life poor, you want to see what being really rich feels like."

"Well, if you're sure, we'll give it a try. It will only be for a short time though."

I went out, after getting off the phone, and finished up with the car. When I got back inside, I phoned Ken and told him I was going to be gone for most of the weekend, and asked him if he needed anything before I left. He told me that he'd be in his apartment working on his problem all weekend, and would call me on Monday to give me a progress report. I went in to take a shower and get ready for my date. In the shower, I started thinking of what Diane had said about wanting bigger tits this time. I naturally started reviewing tits in my mind, and, almost before I knew it, my thoughts turned to Carolyn. I remembered her tits, which were the most magnificent ones I'd ever seen.

<Can you go into my memory and find an image of Carolyn Adams? Get one that shows her naked on top. When I tell you to, I want you to put those exact same breasts on Diane. Can you do it?>



I picked up Diane. She had been waiting near the street when I pulled up, and came right over and got in my car. She was wearing a dark green sweater that showed her hair color and fair skin off to good advantage. She had on some jeans and penny loafers too. The sweater was very loose on her. I was happy to see her again. When she didn't call me for so long, I had started thinking she might not ever call me. She was smiling at me after she got herself settled in the car.

"Hi, Jimmy."

"Hi, Diane. You look nice. Shall we stop and eat something first, or do you want to go flying first and then we'll eat later?"

"I'm hungry, but whatever you want is okay with me."

"I'm hungry too, let's go pick up a couple sandwiches and soft drinks at the sandwich place, and we can take them and eat while I'm doing my preflight checks." She nodded her assent to me, so we did it. It took me some time to get up in the air because I wanted to top off my fuel. It held about forty five gallons, and I wanted to make sure we would have plenty of time in the air. I was planning on flying up towards Victorville because I had some ideas about investing in the area because prices were so low, and I could pick up some larger parcels relatively cheaply. We finally were ready to get airborne, and I took us up. Diane kept looking over at me as I piloted the plane, heading North towards the mountains. Finally, she couldn't hold out any longer.

"Aren't you going to do it?"

"I'm doing it. Do you want to fly it for awhile?"

"Are you just going to tease me then? That's okay. I'm not going to beg you to do it."

"Go ahead and grab the yoke, I'll handle the foot pedals. Have you got it?" She reached out and took the yoke. I kept my hands on mine until she got the feel for it, and then I let go. "That's it, not too much, try to keep it level. Good job."

<Do it now.>

Suddenly, Diane's sweater filled up. She jerked the yolk back, and I took over to make certain we didn't stall. As soon as she saw that I had taken over she released the yoke and started admiring her new attributes. She pulled the bottom of her sweater up to get a good look, and then took it right off when it bunched up in a way that prevented her view. She had no bra on underneath. When I saw those breasts, I knew immediately they were too much for Diane. What had looked so good on Carolyn looked somewhat grotesque on Diane's much thinner frame. Her shoulders weren't anywhere near wide enough to support breasts of Carolyn's size.

<Keep them the same shape, but reduce them by thirty per cent of their mass.> These newly reduced breasts looked great on her, and the guardian had kept them sticking straight out the same way Carolyn's had been. They matched Diane's body perfectly now. After a minute, I was unable to see clearly because looking at them had caused me to think of Carolyn again. I was crying when I turned my head away. Not a good idea I thought, not good at all. It took me only a short time to regain control and to stop crying. Diane had noticed me turn away, and she could see my tears. She asked me if I wanted her to cover up.

"No, don't do that. Those look great on you. It's just that you reminded me of someone when I first saw them. I'm fine now. How do you like those beauties?"

"I love these, but those other ones were too big. They might fit Kate Smith though."

"Actually, they fit a girl who wasn't even as tall as you are. She had a bigger body type than you do, and had much wider shoulders too. They were just absolutely perfect on her body. I was just remembering how they looked on her for a minute."

"I love the shape of these, and the way they stick out like they do. These are very pretty, much nicer than those other ones that you let me try. Would you like to feel them? I don't mind. I'd kind of like to see what it's like to be felt up with big ones like these."

I reached out a hand and started playing with them. They felt like regular tits to me, not like Carolyn's at all. There was a little bit of familiarity, due to the shape, but it didn't seem like I was feeling Carolyn's breasts. I had been worried about whether it might feel like hers. It was a few minutes before I quit playing with them.

"How come you stopped? It felt nice. You have soft hands."

<Turn them back to her regular breasts.>

Her regular breasts were really small, not an A cup like I'd thought before. Perhaps more like the fried egg yolks, she had earlier described them as. When they were changed back again, I noticed that she immediately became self conscious, and reached for her sweater.

"Don't cover them. I want to play with these too." I reached over to touch them, but she had covered them with her hands before I got to them. "Come on, I get to play with these too. It's only fair." She slowly moved her hands away, and I spent time playing with her slightly raised and puffy areolas and nipples. She had about walnut sized breasts, certainly not any bigger. As I toyed with them, she began to relax, seeming to enjoy my touch at least as much as she had earlier, when I had handled the bigger ones.

"Disappointing, aren't they?"

"In what way?"

"Being so small. I've seen eleven year olds with more chest development than me."

"I think they are very nice. Haven't you heard that good things sometimes come in small packages? When you're forty, you'll be glad that you don't have big ones, believe me."

"You wouldn't think so if you were a girl. Suppose you had a small penis? It's similar for girls with nothing on top."

"Who said I didn't have a small one? My whole family is noted for having dicks on the small side. Everyone except for my Uncle Frank. He has a full four inches just like everybody else."

"I hate to tell you this, Jimmy, but four inches is pretty small too."

"Really? We all thought it was huge. Mine is three inches, and only just barely, and that's when it's really hard. Are you sure that four isn't the normal size?"

"I'm pretty sure it's more like six inches, Jimmy. Sorry."

"You're kidding me, right?

"I've seen some even longer."

"Well, of course longer. I was talking about width." It took her a minute, but she finally started laughing.

"You wish. I'll just bet you weren't talking about width."

"What would you like to bet?"

The entire time we'd been talking about this, I'd been massaging her breasts. I could see, by her facial expression, and by the way her nipples stood out, she was enjoying my attention to them. I continued to play with them, running my thumb lightly over the raised bumps on her areolas, and, occasionally, flicking her erect nipples.

I could have done more, but I was also trying to keep the plane aloft too. I stopped playing with her, and concentrated on looking out at the landscape below. We had passed the summit, and were quickly coming up on Victorville and Apple Valley. There were several areas I wanted to take a closer look at. We flew over two areas of particular interest to me three times before I was satisfied that I had seen enough. We had just come around, heading back towards Santa Ana, when my engine started making a coughing, sputtering, choking noise that didn't sound good at all.

<What's that noise?>

Your fuel line is clogged with impurities.

<Can you fix it?>

No, but if you can land, I can direct you to the problem and advise you about how to correct it.

I had already started a descent towards what appeared to be a paved road, two miles south of, and a mile or so east of, the town of Victorville. My adrenaline had really kicked at the prospect of losing the engine and having to make an unpowered landing, but as we neared the road, I started becoming calm again. Actually, the landing was pretty routine, and the engine never did die out on me. After we had landed and stopped, I turned the plane around, so we were facing back the same way we had come in, before turning the engine off.

There is more of this chapter...

For the rest of this story, you need to Log In or Register