Why Didn't I Just...
Chapter 15

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

Desc: Erotica Sex Story: Chapter 15 - 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.



Friday morning, I hurried off to my classes. There was some excitement in our real estate class after the instructor announced that he'd be hiring two part time assistants, from within the class, to help him with a new housing development project that he was working on. Not surprisingly, we learned the following Monday, that the two prettiest girls in the class had been selected to fill those positions. These selections were supposedly based on the one paragraph essay that each interested applicant had to write and hand in prior to the end of class on Friday. I was amazed that no one else seemed to catch on to what he was doing. I hadn't entered myself as an applicant, so it didn't affect me in any way, other than to be amused by his blatantly obvious technique.

As soon as the class ended, I went out to my car and drove right over to Donna's house. She was ready by the time that I got there, but I still had to endure several minutes of conversation with her mother before we could get out of there.

"You rich boys all think that you can get away with anything. You better not get her knocked up. I should make you give me some money though, just in case."

"Why do you spew that garbage out at me? What did I ever do that gives you the right to say these things to me?"

"I've got the right to look out for Donna Jean's interests, I'm her mother. Just because she doesn't bother to think about her future, that doesn't mean that nobody should."

"Well, she won't have anything bad happen to her while she's out with me."

"If it was up to me, she wouldn't be going with you today."

"Donna, are you ready? I can't take much more of listening to your mother."

"I'm ready, let's go. Bye mom. Don't worry, I know what I'm doing. We're just going to have a real good time. I'll tell you all about it when I get back." We went out and I put her bag in the trunk of my car. Soon, we were out on the highway, driving towards Los Angeles. From there, we'd go due West, then we'd head North, up the coast route from Santa Monica.

"Your mother sure doesn't seem to like me much."

"She would like you, Jimmy, if she knew you. She just always worries about me, that's all. She's afraid that you'll do something to hurt me. She says that some people always take advantage of other people, and that people like her and me, we always get used, and then dumped. It happened to her a bunch of times when she was young. She got pregnant with my older brother, and then she was dumped."

"So, now she thinks that every guy you go out with will do the same thing to you?"

"Rich guys. When she got pregnant, it was from a rich guy. Anybody who has any money at all though, is a rich guy to her. After you left, both on Wednesday, and again last night? She had me tell her everything that we've ever done together, from the first time that we met. I showed her the bathing suit that you bought me, and I even told her about the big tip that you left me that first day at the A&W. She wanted to know everything, even about the motel rooms that we got, and about all of the places that you've taken me out to eat. She even wanted to know what I ordered when we ate out. She wants to know everything that we're doing. She's still worried about how it will all turn out. She doesn't want me to get hurt."

"What do you think? Do you think that I'm going to hurt you?"

"I don't know, Jimmy. If you do though, it will still be worth it to me because you're treating me so good right now. My mom said that too, kind of, 'go ahead and enjoy it now', she said, 'because it never lasts', but, I just told her that none of my other boyfriends ever lasted either. At least, this time, I'm being treated good, and I'm being taken to some nice places for once. My mother always tells me that it was bad for her, but, all these years later, she still remembers every fun time that she had with those rich guys. It was just, at the time that it was all happening to her, she never thought that she'd get dumped at the end. She was surprised when it happened to her. I've heard all about it from her, a hundred times at least. If that happens to me now, it wouldn't be a surprise to me."

"I would never hurt you deliberately, Donna. I'm not saying that we'll always be together, because I don't know if we will or not, but I really do like you, and I want us to enjoy what we're doing together now."

"Jimmy, it's all right, really. Let's just have a good time. My mother has her own fears. I'm not afraid. I don't expect you to marry me or anything like that. It will be enough for me if you just treat me nice while we're together."

"I can do that, and I will. I promise. Where do you want to stop for lunch? How about Santa Monica, for some shrimp?"

"Shrimp? Sounds good. How far is it? I'm already pretty hungry."

We drove over to Santa Monica and had a real nice lunch, sitting outdoors where we could see the ocean. We didn't hurry, so it was after four o'clock before we got back on the road. We found ourselves a nice place to stay in Oxnard, not too far from the ocean, and we spent the night there. We went down to the beach that night, just holding hands and walking barefoot in the damp sand, close to the water. I talked to Donna about my classes, and she told me that she was getting some good practice in on her roller skating, but, she said that she was still a little shaky with her stopping and starting.

We stayed out on the beach from the time that we finished eating our supper until it got pretty late, maybe eleven thirty. I had left my watch in our room. We slept together through the night, with her pressed in tightly against me, and me cupping one of her boobs. It was the first night that we'd ever spent together. My first night sleeping with anyone. I enjoyed all of it. Donna seemed pleased as well. We made love two times in Oxnard, once when we first got into the room, and then once more, right before we went to sleep. There wasn't that sense of urgency about either time, and it was comforting to not be in any big hurry or to feel like we had to make use of limited time together in that way.

We had just gotten into the car on Saturday morning after checking out of our room. It was still early. Donna and I had showered together, and we had done some fooling around while we were in there. After we got out, I was very ready to finish things up on the bed, but Donna wanted us to hurry things along and go right away to Santa Barbara. She was real excited now because I had told her, in the shower, that we'd be getting ourselves a real hotel room rather than a motel room, and I had also promised her that we'd eat at least one of our meals by ordering in room service. She had seen that done in the movies before, and she told me that she'd always wanted to get a nice meal delivered right to her room. I didn't want to keep her waiting, since I could see how excited she was by it. So, before nine o'clock even, we were back in the car and heading North. We had been traveling for less than five minutes when I heard from the voice again.

Jimmy, you'll need to detour in Ventura in order to pick up that money. Do you want to do it on the way up or on the way back?

<How long is it going to take?>

No more than a quarter hour. It's buried in a garden at the Mission, so it could be a sightseeing side trip for you two as well.

<Donna's all excited about getting to our hotel. I don't think she's interested in anything else right now.>

Do it after then. I need to tell you, Jimmy, that Donna is more worried about you dumping her than she's been letting on. Her mother has her almost convinced that you're just taking her on this one final fling. That's one of the reasons that she wants to squeeze as much as she can from this experience.

<How do I convince her that it isn't going to be like that?>

Start talking about other trips. Mention a specific place that the two of you will be going to. Catalina Island is one place that she's always wanted to go to. San Diego is another. If you really want to make her excited, ask her about taking a train up to San Francisco for a weekend. Any one of these, if she believes that you really mean it, would stop her worries. Jimmy, if you really want to make her happy, tell her that she can bring her mother to Catalina Island with you.

<You're kidding, her mother? I couldn't put up with her for a single hour, let alone a full day.>

It would mean a lot to both of them, but it's up to you.

<Let me think about that last one.>

"Donna, I'd like to go visit the Missions in Santa Barbara and in Ventura while we're up here. Is that all right with you?"

"They're just a bunch of old buildings and a church, Jimmy, there's not that much to see. I went on field trips to a couple of them when I was a kid. If you want to go though, I guess we could."

"One of these days, real soon, maybe on a weekend, do you think that we can take a train trip up to San Francisco? I hear that it's a very nice train trip."

"Do you mean it, Jimmy? I've never taken a real train trip, and I've always wanted to go to see San Francisco."

"How about the weekend after next? I'll get the train tickets and make hotel reservations, and we can leave on the first train after my classes let out that Friday. We'd have all day Saturday to sight see, and then come back on Sunday. They've got some really posh hotels in San Francisco. We'll stay at one."

Donna had already been sitting close to me, but now she got even closer. She had both of her hands touching me. One on my arm, and one on my thigh. Her head was resting on my bicep. I felt a little shaking on my arm, and when I looked down, Donna was crying.

"Are you okay? Did I do something wrong?" She moved a little bit away and wiped her hands across her eyes. She took a couple of deep breaths, trying to regain some control of herself.

"No, it isn't anything bad. It was something that my mother told me, that's all."

"Something about me, or about us?"

"About how guys take a girl on a big trip right before they dump them. She said that's what this trip was for. She sounded so sure, I guess that, maybe, I kind of believed her. So, when you said that about San Francisco, and talked about us going there, well, then I knew for sure that she was wrong, and that I didn't have to be sad about this trip winding up being the end for us."

"Donna, your mother is wrong about how things work with me. I don't care what her own experiences were, because none of them were with me. She's just wrong to say that about us. I really like you. I like being with you, and, I like doing things with you, things like taking these trips, or going to see new things with you.

Your mother has had her own experiences, good or bad, but they don't have anything to do with what you and I are going to do. Maybe, if she went with us somewhere, she'd see that things are different with us, and she'd quit worrying, and more importantly, quit making you worry. Do you think that she'd go with us next Saturday, out to Catalina Island, on that boat? If she saw how much fun we have together, she would know that it isn't just me using you for sex, because, that's what she really thinks it is."

"You mean for us to take my mom with us? We couldn't do anything together, not if she was there. I don't know, Jimmy. It would be a little strange to me. I've never taken my mother on a date with me before. You know the way she talks too. Wouldn't you be embarrassed by having her say those things to you like she does?"

"So, is that a no to going to Catalina Island next Saturday?"

"No! I want to go there with you. I don't think you should invite my mother though. Really, it would just be too different."

"I'd like her to see you and I together, Donna. We aren't anything like she thinks we are together. She should know that we're different from what she fears."

"I'll ask her, Jimmy, but I don't think she'll want to go either."

"Well, either way, you and I will be going. So, now, we've got plans for this weekend, and the next two. I want to take the train down to San Diego too, one of these days, and maybe spend the night down there. Have you ever been to Mexico?" She looked up at me when I mentioned Mexico. Her face took on a fearful look for just a second.

"I went to Tijuana once with my parents when I was little. It was dirty, and I got scared by some dogs. I almost got bitten by three dogs. That's all I remember about it. I'd like to go to Dan Diego though. I think we drove through it, but I don't remember anything about it."

<What happened when I mentioned taking her mom with us to Catalina Island? I thought you said she'd like that?>

She suddenly got afraid that her mother would drive you away from her. She's also afraid of things that her mother might tell you about her. She and her mother have been at odds over Donna's past activities with boys and men. Her mother doesn't miss much when it comes to Donna's love life.

<What should I do? Should I say something to her, maybe reassure her in some way?>

You should let her work it all out for herself. She's being fed conflicting information right now. She needs to sift through it and decide for herself where the truth lies. This is a very good development actually, because it will speed up her acceptance of the fact that she is a better person than what she's been told and led to believe. It will help to convince her that she deserves to be well treated by men. The differences between what she is seeing coming from you and what her mother has led her to expect from men, will change her future expectations, and weaken the reliance she has had on her mother's values and standards. It is going quite well, Jimmy. You are making great progress with her.

<Is it mostly her mother that gives her this low self esteem?>

Her mother, and every single time that one of her mother's fears for her have been validated by her own selection of boyfriends. Donna has always looked for someone to treat her just like her mother told her to expect to be treated. Until you came along, she always succeeded in finding someone to treat her rather poorly.

<Can it really change so quickly, in a month or two?>

It is already happening, ever since that first day. It isn't difficult for her to see the difference, and decide that she prefers being well treated. Deciding that she deserves to be given this better treatment, that is what will take another month or two.

<This Mr. Wonderful, was she with him the last time through?>

Eventually. This time I'm moving up her meeting him so that it will be three years sooner, and I'm also eliminating a lot of the negative experiences and the guilt that she went through the time before. I hope that this time she will feel that she deserves to be loved and treated well, and that she'll be able to fully enjoy the life that she can lead. She won't constantly have to worry that her past activities and mistakes will somehow be discovered, or that such a discovery would bring either shame or suffering to her husband and children.

We drove up to Santa Barbara and I rented a large room with a good view of the ocean at a nice hotel situated close to the beach. We were allowed to check in early, because the hotel wasn't at all crowded. After we had enjoyed the view, and the really nice amenities of our room, we walked into town and looked for a nice place to eat. We went into a few clothing stores and then did some other window shopping along State Street. I talked Donna into letting me buy her three skirts that were very reasonably priced. they were full pleated skirts, made of a light, cottony looking material. They were each a different combination of a bright, multi colored pattern, and, after she tried each of them on for me, she looked so good in all of them that I just had to buy them all for her.

It was in that store that Donna got the skirts, that she asked the girl who was waiting on us about any of the good restaurants in town. It was really funny because, according to the girl at the store, our hotel had one of the best restaurants in the whole town. We finished our window shopping at about one or so, and then walked back to our hotel. Neither one of us had brought any fancy clothes with us, and the restaurant looked very fancy when we were standing in front of the entrance to it. Donna was at first afraid that we weren't dressed for such a fancy place, but I figured that it was only for lunch. I asked the man at the entrance about a dress code, but he said that we were fine, and that they permitted casual dress at all times.

We told him that we were staying at the hotel, and he led us to a nice table, near a big picture window. You could see the sand when we were seated, but could only see the water if we were standing up. Donna and I both tried to order the lobster dinner, but we were then told that it was only served after four in the afternoon. Strange, I thought, but our waiter told us that the luncheon selection was actually pretty limited, even though he'd given us the regular dinner menu when we first sat down. We finally decided on pastrami sandwiches with a side of cole slaw and pickles. It was all right, but not especially good like I'd been hoping for. It took a little something away from the whole dining experience.

After lunch, we went up to the room and spent the rest of the early afternoon making love. When we were just getting started on the bed, Donna gave me a blow job. She had claimed never to have done it before, but, based on the way that she did things, I had to take that assertion of hers with a big grain of salt. In my other time through, I had spent a fair amount of time with hookers, women whose job it was to know how to give good head. I thought that I could tell the difference between a novice and someone who was experienced. I'd have to rate Donna's performance as experienced, very experienced. I was thinking about whether I wanted to say something to her, when the voice spoke.

Let her bring it up, don't say anything to her now. I didn't say anything, just enjoyed what she was doing. When I was ready to cum, I told her, but she didn't pull away. She swallowed it all, and then came up so that I could hold her in my arms.

"Did that surprise you?"

"I was too busy enjoying it. It was wonderful. Thank you."

"I wanted to surprise you with my knowing how to do that. I told you before that I had never done that, but, that was before I really knew you, Jimmy. I don't do that with every guy I date, but I have done it with some, ones that I really liked a lot. Some of that other stuff, I have done before too. It was just that most guys seem to prefer to believe that you haven't really done that much before them. I'm sorry that I lied to you, Jimmy."

"Donna, you don't have to lie about anything that you did before me, or hide it either. We both enjoy what we're doing together, at least I know that I do. That's what's important to me. That we both make each other feel good, and that we do what we want to together. Is there anything that we haven't done before that you'd like to do?"

"Nothing new, but I really like it when you do me with your mouth, Jimmy. Nobody ever did that for me before, I swear. You're the only one. A guy I went with almost did it once, but then he kind of stopped before he got there, and just kissed me a little bit on my legs while I sucked him." I spent the next hour kissing her and licking her all over. Making love to her afterwards, was a sweet repeat of all of our earlier times. It was a peaceful thing with us, and it always left me sated and content.

At six thirty, we called room service and ordered ourselves two full lobster dinners, along with several side orders. I'm sure that they seldom had orders that included baked potatoes and French fries both, but both of us ordered that. We also got corn on the cob, and, a whole chocolate cake. The dinner was both messy and fun. If you've never eaten lobster pieces soaked in butter from a pretty girl's navel, take it from me that it's enjoyable. That room service was a wonderful investment. We could never behave like that in a restaurant.

We ate the cake the next morning, right after we both woke up. We spent an hour walking on the beach together that morning. We showered together again, made love, and then checked out of our room and drove over to the Santa Barbara mission. Donna was right about it not being that much to see, but I still needed to go to the Ventura mission to find the money that the voice had said was hidden there.

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Story tagged with:
Ma/Fa / Consensual / Time Travel / Historical / DoOver /