10. Linda's Family Evolves - Pt. 01

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Linda makes a more intimate connection with Bobby.
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Part 1 of the 5 part series

Updated 03/16/2024
Created 12/18/2023
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And so the summer was beginning. Bill left for San Diego after a great going away party. And I, of course, sent him off with the best sex I could devise. I will genuinely miss Bill. And I hope we keep in touch. My harem was down from six to three and that made me sad. There was nothing I could do to get Ken or Desi back, but I truly cared for them. And still do. But there seems to be no way to keep in touch with them. They just couldn't handle the sex thing. I guess not many men could.

But I must bring you up to date on what happened outside the house. I mentioned the way I came into contact with Bobby. It was after one of my nude modeling jobs at the college. On my way home in a secluded field I inadvertently came upon him masturbating behind a tree. He had been one of the students drawing me that day, and I had turned him on. More than he could stand for long; he couldn't wait to get home to jerk off. And it turned me on that I had turned him on. Long story short, I gave him a hand job and then walked the rest of the way to his apartment with him.

After that I would meet up with him regularly after that class. Usually we would just walk back to his place together. I had decided that I would not favor him with a hand job unless he was particularly horny. But he is a guy, after all. He was always particularly horny. Also, I was his only female acquaintance. I didn't mind helping him out, but I was concerned that he might become more demanding, or that he might get romantic. I was watching him closely for any danger signals, and I made it clear that I was not open, at this point. He knew I had "boyfriends" and he took what I did as kindness and not romantic at all.

As I got to know him, and felt more safe around him, I could see that he was really a good guy. Good but damaged like me. He had grown up the third in a large family on a little subsistence farm about fifty miles away. He had been home schooled and had come to the college here on a scholarship he had won. Good scores on tests and a good portfolio. But he was socially awkward, as you might expect. His family had been pretty isolated, deliberately so, and he was painfully shy around women especially. He just needed a girl friend who was not me. We had both been damaged by our upbringing, but I had escaped from mine more easily than he was escaping from his. Gary had helped me; I thought I might be able to help Bobby. His sexual tension was enormous. He clearly could not handle being single. I was sure he had to masturbate every night, maybe more than that. And he had his nude sketches of me, and I knew he masturbated while looking at them. Getting an eye-full of naked women wasn't why he took the drawing class though. He was a very good sketch artist, much better than I was. I was turned on by the realism of his sketches of me in class naked. Much better and they would have been almost photographic in quality.

I explained about our house, that we had a group marriage, that I was living with four (at the time) guys and that they were all my "boyfriends". It was a completely new idea to him, but after his shock he seemed to accept it all without judging. Not judging is not that easy to do, either. To accept something you don't really understand, have never imagined, could not even have existed in the world you were raised in, is hard. Especially if it is something sexual.

So the question was, could he become an addition to my "harem"? The question was probably churning around in his mind too. But when we all began living together, and having sex, we had already been a tight group of friends. Introducing a new guy, a stranger to Nick, Matt, and Derek, would be considerably more complicated. They would need to become close friends with him first. It would take time. I don't know if Bobby realized how complex it would be. But he was lonely. I did enjoy spending time with him, that one afternoon each week, and that may have helped him with his loneliness, as well as his sexual tension a little. But a hand job once a week won't go far. The only relatively quick solution for him would be for him to find a serious girl friend somewhere.

And so it was, in one of my weekly meetings with Andrea, the militant feminist, his name happened to come up. I mentioned that I had become friends with Bobby and she asked, "Bobby who?"

Then I realized I had never asked his last name. "Just Bobby. I never asked his last name."

"You met him in class?"

"Yes, he is a freshman this year, art major. He is advanced and is taking some upper level drawing classes."

"Oh. Let me guess. You were a nude model in one of his classes and he tried to pick you up?"

"Yes. But not exactly like that. He didn't try to pick me up. I was walking home across the fields and I accidentally surprised him masturbating."

"Ah. Accidentally?"

"Yes. I am sure it was an accident. I have seldom seen anyone that embarrassed."

"Describe this guy."

"He is maybe shorter than average. Red hair. Very skinny. Bad complexion. Blue eyes."

"Wait a minute. I know this kid. Rents an apartment in town?"

"Yes. How did you meet him."

"I am a TA in an intro to sociology class and he is in it. But his name isn't Bobby."

A sudden stab of fear. "What do you mean?"

"His last name is Bobbington. Some old English name or something. His first name is so weird he has every one call him Bobby."

Relief. "What is his first name?"

"Almanzo, I think. Something like that."

"Oh! Like in the book!"

"Book?"

"Yes, it is one of the Little House books. People from my social milieu commonly use it in home school."

"You were home schooled?"

"No, but I know my people. They are pretty good books, actually, mostly."

"By 'social milieu' I assume you mean narrow bigoted backward fundamentalists?"

"That is not a fair description, not for all of us, but yes, something like that."

"OK, so this guy is damaged goods. You like to pick up strays, don't you?"

That gave me pause. What other strays had I picked up? The guys in the house? I suppose Bill would have qualified as a stray, though I preferred to think of him as a lost sheep. "Yes, I guess I do. Bobby is damaged, but in the same way I was. If I hadn't met Gary back when I was a senior I would probably still be back in my home town trying to cope with things. Maybe I can help him out."

"Wait. Have you had sex with this guy?"

"Yes and no. I haven't done more than give him a hand job."

"And he hasn't tried to push for more, to take advantage of you."

"Not at all."

"Hmmm. I am skeptical that any man's intentions can stay good when the possibility of sex is involved."

"I understand. I am watching for the warning signs. I explained to him my living environment, and that I wasn't open to any kind of romantic connection with him."

"Trust me. He doesn't want romance. He just wants sex. Though he might not be able to tell the difference."

"You may be right but I think I will notice the signs if anything starts going wrong. And I will run if I do."

"Good. I think you have been really lucky with the guys you've got. How big is your 'harem' now?"

"I am down to three. Bill left for San Diego after finals. He got a good job down there."

"Well, be careful. If you pick up many strays you are in danger of becoming a sex therapist. Though your methods are unorthodox to say the least."

That got me to thinking. Maybe I really could help the sexually wounded people escape from their youth. And it could be fun at the same time. But I knew I had better be careful. Sex is powerful stuff. Like C4, or whatever that stuff is that blows up.

At any rate, I decided to take things up a notch. It was the beginning of the summer I decided that I would give Bobby a blow job. I was sure Bobby was a virgin, like Ken had been, and if he thought the same way as Ken he would not consider a blow job as a violation of his virginity. That is a form of logic I just don't understand. If a guy has an orgasm in your pussy he is not a virgin but if he has an orgasm in your mouth he is still a virgin? It doesn't make sense, but sex is not exactly a rational activity.

I did have a sexual relationship to the three guys in the house, an intense one, but we had not made vows to each other. There was no assumption that we would be exclusive to each other. I knew that all three of them had women outside the house. They had all had girl friends before we had become a thing all together. There was no idea that we were all supposed to be faithful to each other. Even I, as the "house slut" was not under any obligation to them for my outside activities. There was no rule that kept me from having sex with Bobby except the fear that he would either become possessive on the one hand or broken-hearted on the other.

In summer, there were summer classes, but Bobby was not in one with me, either modeling or as a fellow student. So we kept meeting up on Thursday afternoons and just visiting. Typically I would walk him back to his apartment. There I would take off my clothes and if he was hard -- he was always hard -- I would help him out. Then we would hang out for an hour or so and just talk about whatever. He really liked it that I kept off my clothes, and I enjoyed him seeing me too.

So fairly early in the summer, we took our usual walk home chatting about everything. He was interested in everything. As usual, when we got to his apartment I took off my clothes. Typically he already had an erection just out of anticipation. He didn't need me to be naked and he never tried to touch me or take advantage. How many men would be that cautious of me? Normally I would unzip his pants and take his dick out, but this time I said, "You should take off your clothes too."

He looked frightened. I knew that feeling, though I hadn't been frightened about people seeing my body for two years now. "Why?"

"Because this time I am going to give you a blow job." His mouth popped open and his eyes got very round. I unbuttoned his shirt and peeled it back. He was standing up so everything was easy. Then I unzipped his pants and pulled them down, And then his underwear. I guess he felt more exposed being totally naked because he made as if to hide his dick. But I had already seen his dick many times now so it was just his insecurity that made him do it.

I took hold of his dick like I usually do, wrapping my fingers around him. Then, instead of beginning to massage him, I knelt down in front of him and licked just the tip of his dick. A groan of pleasure went through him. He was uncircumcised so I used my tongue to peel back his foreskin the rest of the way, and took the head of his dick in my mouth. Then I pushed my face against him and took his whole dick in my mouth. His penis was a decent size, but his body was so skinny that it seemed even larger in proportion. I didn't have much trouble getting his whole dick in my mouth. When I had it all the way in so that his balls were against my lips, I moved the back of my tongue back and forth across the head of his dick. It must have felt really good. I doubt it took even a minute before he came. And so much semen! I swallowed as much as I could with each ejaculation but I couldn't get it all. Some dripped down from my mouth and down my chin and onto the floor. Of course, usually his cum just squirted out all over the floor, so this wasn't much to deal with. When I was touching him his ejaculations seemed like the normal amount, but it sure felt like more in my mouth. Maybe getting his first blow job had stimulated more semen? I don't know. His semen tasted saltier than what I was used to. I had tasted the semen of seven guys before Bobby, and his was the saltiest, but not unpleasantly so. I like the taste of semen.

He didn't say anything. He was just breathing very hard, like he had run up the stairs. But he was pretty wobbly after his orgasm. I laid him down on the bed, and then I laid down beside him. We just laid there side by side while he gradually recovered. I watched his dick deflate slowly. We spent half an hour or so and didn't talk much at all. Just lying side by side naked.

But time marches on, as they say. "I have to go now, Bobby."

"Oh. Ah, OK." I got up and started putting my clothes on. "Uh, Linda?"

"What?"

"Thank you."

He was the first man who had thanked me for sucking them off. Maybe the guys in the house were taking me for granted? I smiled then. "You are welcome. I had fun too." A pause. "I will see you next week, right?"

"Yes. Yes."

I had mentioned to the guys that I was seeing Bobby regularly. They were curious about meeting him, but not urgent about it. They took it for granted that I was probably having sex with him. But no one felt the need to talk about it.

It was the end of summer. I was going to spend the last week of August at home visiting my parents, and I hoped to see Gary while I was there. It was the last week I was hooking up with Bobby before I left, and that is when I decided it was OK to let Bobby fuck me. Early afternoon and I had just come out of a class in which I had modeled so I was pretty turned on. Having those students looking at my naked body for three hours was always a turn on. Bobby met me at our usual rendezvous spot. He had gotten a summer job as an assistant at the school library. He needed the money. His parents had very little.

As we were walking back to his apartment, we got to talking about my trip home. I would be leaving in two days and wouldn't see him again until all the dust settled in our next semester schedules. We were both in good moods, excited for the new year, happy at how the old year had gone. Bobby was really glad he hadn't gone home for the summer and I was too. Before we got back to his place, as we were both beginning to anticipate what we would do there, I decided it was time to give him a head's up (no pun intended). There was a pause in our conversation.

"I think we should do things a bit differently this afternoon. If it is OK with you."

He was cautious. I knew he counted on my weekly favors. "Yeah? What were you thinking?"

"I think it is time that you fuck me."

He halted in his tracks, entirely surprised. I guess it is not surprising he was surprised. He knew I didn't want our relationship to evolve into a romance, and he probably equated fucking with falling in love. It is not a rare error.

It took him a while to figure out what to say. "Are you sure? I mean, that would be great. That would be more than I hoped for. But are you sure? I mean..."

"Yes. I am sure. I am not saying that I am in love with you or anything. I am saying that I trust you enough that you will keep our relationship in perspective. You will, right?"

"Yeah. Yeah, sure. But won't you're uh, boyfriends, mind?"

"Not at all. We don't have that kind of closed relationship. They would be totally OK with it. Each of them have outside relationships as well."

He thought about it for a while. "I guess I don't understand."

"That's OK. I don't think many people would understand. All you have to do is accept it at face value and not get nervous or anything."

"You know I've never..." He let it trail off, embarrassed.

"Bobby, of course I know you are a virgin. If you don't mind losing your virginity to me, then there is nothing to worry about." He still looked worried. "Look, don't worry about your performance. I will show you, teach you, all you need to know. You don't need to be embarrassed."

There was still something bothering him. "I would feel like I was just using you."

"And that would be fine. I want you to use me. That is what I am offering. You can fuck me and I will guide you every step of the way, and at the end I hope you will have the best intro to fucking possible. I expect you to use me and I will enjoy being used. This will be a good thing. For me, but I hope especially for you."

"OK." We were arriving at his apartment by this time.

"I think we should start out like we usually do and then just gradually proceed." I began taking off my clothes. When I was naked I stood in front of him with my legs slightly apart and my arms hanging down by my side. "Look at me. You've already seen me so much you must have my body memorized by now. You masturbate in front of my sketch, right?" He nodded. "And I imagine you fantasize when you do, right?" He nodded again. "Do you fantasize about fucking me?" He blushed this time and nodded again. "All right. Stare at my pussy right now and fantasize about fucking me." It feels so good when a man is looking at my pussy and I know he wants me. I was getting all hot just watching him stare. "I am going to do my best to make your dreams come true."

I walked up to him and put his hands on my breasts. "You have never touched my breasts before. That showed amazing restraint on your part and I appreciated it. But now you can touch them all you want." At first he just held his hands against my breasts and gently squeezed them. Then he began to massage them a little. I took one of his hands, moved it away and put his fingers on the nipple. "Now squeeze my nipple. A little hard but not too hard. Kind of roll my nipple between your finger and thumb." It was amazing how huge his dick had become. I had probably better not push him too far. I stared at the bulge in his pants and he blushed. "I have seen your dick so many times you don't need to blush now. Let's have it out." I began pulling off his clothes. I didn't want to have another mistake like with Ken. When Bobby did cum, I wanted it all in my pussy.

When he was naked I moved one of his hands to my pussy and pushed his hand flat against me. "Maybe we had better not wait too long. I don't want you to cum prematurely." So I moved over to his bed and lay down on my back and opened up my legs for him. "Now, Bobby, come here and lie down on top of me and I will guide your dick in." He knelt down between my legs and moved down onto me. I grabbed his dick on his way down and moved it to the opening of my vagina as he did so. I had meant to have him play with my clitoris for a while first, but I wasn't sure how long he would hold out. "OK, Bobby, all you have to do is push and you will be inside me."

I felt him pushing his penis inside me, hesitantly at first, and then eagerly, all the way in. I felt his balls between my legs and his dick felt so good I could have screamed. I hadn't realized quite how much I wanted him. "Now Bobby, use me. Just let your dick play inside me any way you want. Enjoy my pussy and when you can't hold back just let it all happen. I want your cum inside me."

He began pulling out and pushing back in, slowly at first, but I could tell he felt so good he wouldn't last long. He began to moan every time he thrust into me, and I could tell he was getting close. "Just let yourself go, Bobby. I'm waiting for your cum. I want to be fucked. Any time. Any time now, Bobby. Go ahead. Let it cum. Fuck. Fuck. Fuck! Oh, fuck me!" And then he was fucking me, pushing his dick as hard as he could when his orgasm started. He barely had time to back his penis up for another thrust when the second ejaculation was on him. Over and over he thrust in as hard as he could and when he was done he just collapsed on me. It was shattering for him.

"And just like that you aren't a virgin anymore." He was breathing heavily, lying there on me with his dick still inside. He could barely talk at first. "I hope that was as good as your fantasy."

"Oh, yes. Yes. I had no idea. I had no idea it felt so good."

"Better than masturbation? Better than a blow job?"

"Oh, yes, yes, yes. Let's do that again."

"You thing you could?"

"I don't know. Just being in you makes me want to fuck you again. I could fuck you all day."

"If you can do it, go ahead."

His dick was still erect inside me and he began moving it again. More slowly this time. I didn't want him to quit. He kept moving in and out, for quite a few minutes. And then I could feel him sort of stiffen, inside, and I knew he was going to do it. Now he started moving more quickly and I was beginning to get close to cumming myself. I didn't think he would make me cum though, It felt like he was going to get there first, but he surprised me. I felt myself getting up there, closer. If he held out a few more minutes I would cum, but he couldn't quite make it. I felt his next ejaculation but too soon. This time, of course, his orgasm didn't last as long. When he came back down I asked him if he could go for a third one, but I could already tell his dick was getting less rigid. I doubt he had anything left to give. He just shook his head.

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