My American Friends Ch. 4

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Tiffany and Natalie plan the seduction of Natalie's Dad.
3.9k words
4.09
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Part 4 of the 5 part series

Updated 10/19/2022
Created 08/03/2002
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From: "nataliebare"
To: sonia_de_beaumanoir@hotmail.com
Subject: Tiffany Returns
Date: July 20, 2002

Hi Sonia.

I'm happy to say that Tiff got back yesterday. She and her parents had gone to Gainesville to help get her apartment set up for the coming year. She will be going to the U. of Florida in September. I'll be going to U. of Miami, but I have to live in a dorm, at least the first year. You told me Sylvie's sister lives in the Miami area too. Maybe we can get together when Sylvie and/or you come for a visit.

I've been celibate for five days; Jane has her period and hasn't wanted sex since our visit to Clearwater. I also think either her ass or her conscience is still smarting. Of course, that doesn't mean I haven't experimented. I borrowed that big dildo from Jane's bedroom and tried it on myself. It is WAY too big for me; I could barely get the head inside before I felt like it was splitting me. I'm still amazed Jane gets it into herself. The dildo from the strapon is a nice size, and I have no problem doing myself with it. I tried it in my ass too, with lots of KY. Once it's in I can fuck myself with it while I finger my clit, and have some very nice cums that way.

Tiff and I spent the whole afternoon together today. I was planning to surprise her with the strapon, but Tiff had some surprises for me first. During the drive to Gainesville, Tiff's mom came out and told her that they knew about her and me being "more than friends." Tiff acted innocent, but her dad said they understood, and at least they didn't worry about her being with me as opposed to some of the guys she had been dating. (Of course they don't know how wicked I'm becoming lately.) Tiff asked them what they thought we were supposed to be doing. She was expecting to hear that Jane had informed on us, but they just said that they had known for quite a while and that parents aren't quite as dumb as we girls might think. They said that Dad and Jane have also known since the beginning. So I guess Dad either knows about you and me, or else wouldn't be shocked if he did know.

Tiff told them that she really likes boys more than girls, and not to worry about her being a lesbian. I was a little more than hurt by this remark, but Tiff said she only told them that to make them feel better (liar!). Maybe they want to see some grandchildren someday. The reality is that she does like boys as much as me, so I need to get over that.

Afterwards, I told Tiff how Dad and Jane had been with some people on the island (I didn't mention names), and how I thought they might be swingers. Tiff agreed and said she wouldn't be surprised if her parents were swapping with them too, although her mom is pretty straight.

Talking about our folks fucking each other was such an interesting topic. I told her it was hard to imagine her dad, who is kind of old and ugly, fucking Jane, who is a lot younger and very pretty. For that matter, old people like that fucking anyone is kind of hard to stomach. Tiff said that she wondered if there was anyone Jane wouldn't fuck, and besides her dad isn't that old. She said she has had fantasies about fucking him herself, and asked if I had the same. I told her I'd never had fantasies about fucking her dad. She hit me on the arm and saying, "That's not what I meant. I mean fucking your dad." Well I have at times imagined it, and said so. But Dad is much handsomer than hers.

Then Tiff said she wondered if our dads ever thought about fucking us. I said I didn't know, but we could probably ask Jane and find out. Tiff said she thought most dads have that fantasy, and that for her to fuck her dad would be like with me and Jane, since they aren't biological parents. I wonder if she was serious about that. Then she said she'd make me a bet: that she could get my dad to fuck her, and if she did I would have to let hers fuck me. That didn't sound like a good bet to me. I told her that to be fair she should have to seduce her mom since I had done it with mine. All this kind of talk got us in the mood for sex, and we went to my room for a quickie, and then for a swim.

After our swim and some lunch, I showed her the strapon. She was hot to try it out. I won't bore you with too many details, but we fucked each other a couple of times each. I discovered my favorite position is missionary, since I love to look into her eyes and kiss while doing it, plus I can play with my nipples at the same time or reach around behind to feel Tiff's pussy under the cock. My pussy isn't sore at all any more, and she can pump me hard without hurting. Tiff really likes doggy best. I asked her if I do it better than the guys she's fucked, and she says I'm much better. Of course, I can pump her until she cums, which can't be said for most guys, and in addition we cuddle afterwards. Even so I'm still looking forward to doing it with a man the first time, even if it's not perfect.

I wanted her to stay for dinner, but Tiff said she had a dinner/movie date that night with her boyfriend (guy who had taken her to the prom). I asked if she was going to let him fuck her, and she said, "maybe." With Tiff that means "yes."

So here I am writing you on a Saturday night. Since I started with Tiff I've turned down all the boys who have asked me out, and no one calls any more. Jane and Dad are out too. I almost suggested to Tiff that we have a threesome with her date, but I want to have my first real cock with someone I like.

Yours in solitude,
Natalie

From: "nataliebare"
To: sonia_de_beaumanoir@hotmail.com
Subject: Sunday Morning
Date: July 21, 2002

Hi again Sonia,

It's early Sunday morning, and Tiff just left the house. She turned up after her date, and tapped on my bedroom window. I was in bed listening to music and doing my nails. I let her in the back door, but there was no reason to keep quiet since Jane and Dad were still out.

She and her date had gone to the movie, but she didn't see much of it since she had her head in his lap the whole time they were there. He came in her mouth pretty quick, but she was counting on that so that the next round he would last. Afterwards she suggested that they go for a ride as the film was less interesting than what she had in mind.

They drove to the bayfront where it was dark and deserted, and climbed in the back seat for a fuck. But even though he lasted a lot longer the second time she didn't get off. The boy was pretty satisfied with himself and drove her home. So she got her car and drove over to see me.

She got undressed and into bed with me, and I ate her. Her cunt was all red and moist inside; I'm not sure if there was any sperm left in her by then, but the thought of eating a pussy that had just been fucked was a real turnon. By the time she came, I had a mouth full of her juice and perhaps some semen too, and I was as wet as I could possibly be. Then Tiff did me with her vibrator, which she had in her purse as always. I was cumming in less than a minute. We lay there together until we had calmed down, and she left.

I'm not ready for sleep yet, and I wanted to write while the experience was still fresh. I'm thinking I should get Jane to do the same thing. Eating Dad's cum from her hole would be so hot. The thought of it is making me want to cum again. I wonder if I could do that if he had fucked her ass; it sounds filthy and exciting at the same time.

Enough! I'm going to go do myself and get some sleep.

Love,
Natalie

From: "nataliebare"
To: sonia_de_beaumanoir@hotmail.com
Subject: Analysis
Date: July 28, 2002

Bonjour ma chere Sonia,

I hope my weak try at French is correct.

Jane recovered from her menstrual funk, and has been eager to play with us all week. We haven't discussed our time with Laura at all, nor has Jane asked me to do anything like what we did there. I'm thankful for that because I don't feel too proud of myself, even if I was tipsy and she wanted me to. I wonder how you felt afterwards the times you were with Jane.

Tiff has been going out on dates all week, so the three of us are together in the afternoons. Tiff does tell us all about her dates the next day. She has sex with him each time. I'm kind of envious, even though Tiff says he's not very good. Jane says she wants to invite him over, and I think she's only half kidding.

When Tiff is here we've been somewhat in a rut, doing the same things over and over. It's still fun, and we have lots of cums every day. All of us take turns using the strapon on the others. Tiff refuses to let us fuck her ass, and I did too at first (more about that later), but Jane loves it. Jane showed us a position she says you particularly like. She gets into a 69 with one of us while the other does her ass with the strapon. The one on the bottom can finger or lick her pussy while finger fucking the one with the strapon from below. I agree with you that this is a hot variation; I like being the bottom best.

One thing that surprised me at first was that the strapon never seemed to come out of her dirty. She told me that she gives herself enemas frequently, not only so that anal is pretty clean, but also because she liked the enemas themselves. I wanted to try that myself, and now we have been doing daily enemas together. At first I didn't much care for it, but now I quite enjoy the experience.

Afterwards, Jane wipes me dry and then puts her tongue in and around my asshole. The sensation is such a turnon, and I bring myself off while she is doing it. She told me that this is called rimming, a word that sounds crude to my ears. She wanted me to do it to her. I refused the first time, but after I had tried it once I found I liked it OK. I don't put my tongue inside though - that's too gross.

Now the part I really wanted to write you about. I keep thinking about what Tiff and I talked about, especially about having sex with Dad. I know it's wicked to even think about it, but every time Tiff or Jane are fucking me I close my eyes and imagine that it's his cock inside me. I'm tempted to ask Jane what she thinks, but I'm still too embarassed to even mention it. Knowing Jane as I do now, I bet she'd be all for it, the little slut. Even if I'm not strictly a virgin any more, I keep thinking that having him be my first man would be a gift to both him and myself. I'll be going to college in five weeks, and won't see them that often. I imagine I might meet some guy there and do it with him unless I seduce Dad before I go. Do you think I'm evil for having these thoughts?

In the meantime I've temporized by learning to have anal sex with Jane. In my imagination I say that since Dad likes it so much, maybe he would like to do it with me too, maybe even more than the regular way. I told you how I've fucked my ass with the strapon dildo manually, but very slowly and carefully. I figured I needed to learn how to take it from another person, so I let Jane do me wearing the strapon. She herself likes it hard and fast, but I must say she was quite gentle at first, and lets me control the pace.

We've done it four or five times now, and I can stand it pretty well. I can say that I actually like it now, and have managed to cum doing it the last two times, although I touch my clit at the same time. The first few times we did with with me on all fours and her behind, but the last time I got on my back and pulled my legs back over my shoulders and my hands holding my thighs apart and being able to touch my cunt. This position feels very open and vulnerable. With my ass at the edge of the bed, Jane can stand and direct the dildo into me. Like with missionary, I can see her face and eyes while she's doing me, and I like that better than when she's behind.

Tiff is coming over this afternoon as usual, and I think I'll let her try my ass as well. I'd like to do hers as well, but so far she refuses to let anyone in.

I'll stop there for now. Please write soon.

Love,
Natalie

From: "nataliebare"
To: sonia_de_beaumanoir@hotmail.com
Subject: Enemas
Date: August 1, 2002

Hello Dear Sonia,

It is late Thursday night, and I just had to write you before going to bed.

I haven't written during the past week since nothing much happened until the past few days. I got my period on Monday, and was in a pissy mood until today. I've had no desire for anything sexual at all, and so Tiff and Jane left me pretty much to myself. It's always been like that with me each month, but until I started enjoying daily sex it didn't strike me that I would feel deprived. Jane says she's the same way but has her way of coping; you know what that is from our previous descriptions. I don't think being tied and whipped would be my recipe.

Luckily this mood passes, and this afternoon I called Tiff to see if she was free. Not only was she free, but we actually arranged a "sleepover" tonight, which we hadn't done since we were both 12. The parents know what that means now, but nobody seems to care much.

Tiff came over early and ate dinner with us. We were all nude as usual. Tiff has been to the naturist camp with us often, so she was happy to strip bare as well. I couldn't help but think that all of us would have looked sexier in swimsuits or underwear. Lately I've been looking at Dad when he's naked and imagining his cock erect. I want to touch it. I've only seen it like that once when I spied on Jane and him, and then it was hard to see much. He doesn't look that big, but Jane says his is nice and he knows how to use it.

Dad and Jane were going to the dog track that night and said they'd be back around 11:30. Tiff and I jumped in the pool for a swim while they were getting dressed, and waved at them as they were leaving. It was still light out and pleasantly warm when we got out of the pool. I got some beach towels to put on the pool loungers, and we lay down to dry off and get some sun.

I asked Tiff why she wasn't out with the b/f, and found out they had broken up. The reason is that he is going to a local community college this fall, and so won't be that close. He wanted her to be faithful (ha!) and they could get together on weekends and holidays. Tiff isn't interested in that, and as she tells me she wants to try a "variety" at school. Anyway, she told him to get lost in so many words. I am thinking that it's good news for me as we could be together more.

I told Tiff about how Jane and I had been doing the enema thing, and how Jane had fucked my ass a few times, so that I liked it now. I said she could do it to me too if she wanted to. We decided to try it later on. When I asked her why she never wanted to try anything anal, her reply was that one time she let an old boyfriends do it. His cock was pretty big and wasn't lubed enough, and when he had gotten the head in it hurt pretty bad. She'd yelled at him to stop, but instead he pushed all the way in. She was screaming and crying, and he pulled out after that, but she bled from it for days afterwards. That was a couple of years ago, and she hasn't let anyone touch her butt since.

This conversation made me a little warm, with me touching myself while she was talking. I said I wanted to show her something, and went over to sit on the foot of her lounger. I spread her legs and got down between them, but instead of licking her slit I started to run my tongue around her asshole and the skin between it and her cunt. I felt her tense up when I first touched her, but after a bit she relaxed and spread her legs even more, pushing her hips up to make it easier for me. Her little hole is wrinkled and very tight; it was clean and smelled of chlorine from the pool. She stroked her clit with one hand and my head with the other, and I alternated between working the tip of my tongue in circles with lapping with the flat part. Tiff was moaning and bouncing her hips against my face, and knowing she was close to cumming I switched to long licks from her ass up to her clit and back again, looking up at her face while I did so. I love the way she looks during a cum; she clinches her eyes shut and moans really loud.

After that session, we both were sweaty and so jumped back in the pool to cool off. I asked if she would like to give me an enema, and off we went to Jane and Dad's bathroom. I showed her how to fill up the bag with warm water and then slide the tip of the tube into my rear. I sat down on the toilet with my feet on the seat, and Tiff knelt in from of me holding the bag. Then she loosened the clip letting the water flow. I love the feeling of warmth inside me and that feeling of being so full you just HAVE to let it out. I pulled the tube out, telling Tiff she didn't have to watch the rest as it can be pretty gross. When the water came gurgling out of me into the toilet, Tiff actually laughed at me saying she always knew I was full of shit. I was actually pretty clean, but I had her do it again to show her that after a couple of times the water does come out clear.

Tiff says I should study to become a sex-ed teacher at school.

I convinced her to try it too. We washed off the tip of the tube, and I put some KY on it even though it is smaller than a finger. She sat on the toilet and the tube slid into her with no resistance at all. I hadn't put much water in the bag either, but even so she seemed alarmed when it was only half in. It takes some getting used to I think. We finished eventually, but she didn't want a second rinse.

Back in my room, Tiff put on the strapon and we lubed it up with KY. I also put some on my fingers and slipped two of them into my rear, to loosen myself up. I find I can relax the ring pretty quickly now. I asked Tiff for her vibrator that she always carries in her purse. Getting onto the bed on all fours, I played the vibrator on my pussy lips and around my clit, while Tiff got behind me and put the head of the dildo against my ass. She had done it to Jane before, and we had a nice rhythm going very quickly. I can push back against it now, so that every stroke goes in deep. After some time, I felt a nice cum starting to build. I pushed the vibrator into my cunt, thinking about how Jane had been fucked by Dad and Phillipe that time. I was yelling, "Fuck Me! Fuck Me!" and was semi-delirious when I had a massive O.

I collapsed on the bed with my ass in the air, with Tiff still embeded in me. She pulled out, and sat down beside me. My asshole stayed a bit open, and Tiff slipped two fingers inside and slowly felt around the opening; she had never done that before, even with Jane. I rolled over onto my back, and Tiff lay beside on her side, with her head propped up on her arm.

She gave me a look, and asked, "Why were you yelling 'Fuck Me Dad' just then." I told her I'd never said that, but she insisted that I had. I finally told her about my fantasies, and how they were her fault from bringing up the subject a while back. She told me that she loved that fantasy too, and that I should make it come true. She was sure that Dad would be cool about it, seeing that he was married to Jane and with all the stuff she had gotten up to. Tiff said she had some ideas about making it happen, as long as I wasn't BS'ing her. When I asked what her ideas were, she said to wait and see.

Then I told her about them and Phillipe and also about them and Sylvie. I hope you won't be mad at me for telling; I'm also hoping Tiff will come with us the next time to St. Martin, and we can all have some fun together. Sonia, I have never asked about what Jane tells you, but if she has said anything about Dad wanting to have sex with me, please write back and let me know.

I guess I've been long-winded, seeing as how big this email has gotten. Jane and Dad just came in and went to their room. Tiff is yelling at me to get off the computer and come to bed, so I will sign off for now.

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