tagLetters & TranscriptsA Correspondence with Sharon Ch. 21

A Correspondence with Sharon Ch. 21


Part 21: The Pittsburgh adventure part 2 and the Easter Surprise

This is the continuation of an email correspondence I had with a woman named Sharon Alderson. If you have not read the previous parts I suggest you go back and read from the beginning to get the full background. This conversation includes elements of wife swapping/sharing, incest, and group sex. If you don't approve of these behaviors and you still read on anyway then you are an idiot and I take great delight in knowing I've made you disgusted. Please leave me an anonymous note and let me know how well I've done.


Apr 04/16/09 06:44AM


Thank you for making the effort to give me so much detail about the Pittsburgh trip. I don't have time to read it all now, so I printed it out. This will allow me to read it over lunch and make some notes. I will try to write back tonight. Just remember to pace yourself. I'd hate for you to get carpal tunnel syndrome!

Before I got your last email I had started breaking up your emails into more reasonable sized files instead of one huge one. Then it occurred to me that with some minimal editing I could interleave my emails with yours and it would make an interesting account. I would like your permission to post them on Literotica.

Your friend,



Apr 04/16/09 10:55AM


When I said I was determined to keep you up to date I was serious. Don't worry about me, I know how to use proper posture when typing. I also take plenty of short breaks on the longer ones like I sent last night (and probably today). I'm fine with you posting our emails on Literotica. I trust you to make whatever editing you feel is needed. Now the rest of the Pittsburgh adventure, as you called it.

After I was done eating Tommy told me to clean up the mess. I guess they wanted a mother as well as a slut. After I was finished with that I didn't know what to do so I just stood beside Tommy. He was rubbing my butt and watching TV and then out of nowhere he says "Hey did you guys know I spanked Sharon a while back?"

That got a "no way" out of Bruce and Scott. To which Tommy says "Yes, she was bad. Tell them Sharon."

I just looked down and said "Yes, it's true."

Bruce looked excited and says "I'd like to see that."

Tommy then looked up at me and said "OK, take the position, slut."

I hesitated and asked him what had I done wrong?

He insisted on spanking me and said he'd think of a reason. So I laid down over his lap like I had before. He put one hand on my back and the other on my butt. "Let's see, oh I know," Tommy said, "You haven't begged me to fuck your ass yet."

Just the mention of that surprised me and I stiffened up. Tommy responded by pressing firmly down on my back to remind me that he was in charge. Remember that before I left I had decided to just let whatever happen. I was still very much in that mood, so I relaxed and waited for the first slap. It came soon enough, followed by a second and then a third. They were about as hard as last time. Not enough to really hurt, but they did sting a little.

"I'm going to keep going until you beg me," Tommy says. Then he started spanking me again, about one a second, alternating between my cheeks. It went on longer than the first time and amazingly I could feel my pussy getting hot. I didn't expect that. Naturally I didn't give in yet.

Then Bruce and Scott wanted a turn, so Tommy stopped spanking me but kept me over his knees. Bruce and Scott took turns, one on each cheek, but they were hitting me harder than Tommy was. I don't think they realized he was holding back. My butt really started to burn and I could feel the tears welling up in my eyes so I cried out, "OK, OK, please stop."

Tommy asked, "Well?"

I knew what he wanted but I was having problems saying it, so I said, "Please don't make me say it, Tommy." I added a little extra wimper to get a little sympathy from him.

It didn't work. He had Bruce and Scott each give me another swat. They let up a little that time, but now it didn't matter. My butt was really stinging. Tommy warned me, "We can do this all day Sharon."

So I gave in. He was going to get his wish no matter how much I didn't want to do it. "Please fuck my virgin ass Tommy."

Now I have had anal sex before, but I wanted Tommy to think it was my first time so he'd go easy on me. He prompted me, "Come on, you can do better than that."

So I begged again trying to make it sound more sincere. I'm sure this was something that Joe started -- the begging. I guess he likes it because it's so degrading and humiliating. It seems like Tommy is really getting to like it as well. There might be another reason too. Maybe you are right and Joe does want me to be a little less passive. That's going to continue to be hard for me since it does not come naturally.

Anyway Tommy let me up and led me to the bed and had me get on my hands and knees. He produced a tube of something from his overnight bag and slicked up his finger. Then he felt around my anus a little with his finger before pushing it in. I begged him to go slow. Mostly he did. Next he worked his thumb in (where did he learn how to do this?) and wiggled it around a little. Then he pulled it out and started moving around behind me. I looked around and saw him spreading some sort of clear jell over his cock and stroke it a few times in his fist. Then he moved up closer and I just put my head down and closed my eyes.

When his cock first pushed against my anus I squeezed down by instinct, keeping it out at first. But he pressed a little harder and it popped in. He went about half way into me instantly and I cried out. It did hurt, but mainly I was just surprised. He paused and when I didn't say anything he continued to press inward. Once he was all the way in he paused and said, "Fuck, if you think her pussy is tight you have to try this!"

He fucked me slowly at first and Scott came up and put his cock in my face and told me to suck it. By then the pain had subsided but it still felt weird so I was kind of glad for the distraction. After about 10 minutes Tommy came inside me and fell backwards onto his back saying, "That was great."

Then Bruce climbed on the bed and told Tommy to get out of the way saying that he wanted to try my "hot ass" too. At that point I didn't care. I mean my butt was feeling strange, kind of like I needed to go to the bathroom, but it didn't hurt.

Bruce lubed up quickly and then started fucking my butt slowly like Tommy had at first. He was even more vocal than Tommy, if that was possible, saying how only a filthy whore would let herself get fucked in the ass and things like that. I think Scott liked that because he came in my mouth right about then. After that Bruce rode me hard and fast for about 10 minutes. Then he said, "I'm going to cum in your hot teacher ass." And after a few more strokes he did.

He pulled out and I collapsed and kind of curled up into a ball. My ass was sore. I didn't want any more anal for a while. Tommy came over and seemed a little worried, asking if I was OK. I told him that I was all right, but that I needed a break and could use a bath to sooth my butt. He said that would be fine, so I made up a nice hot bath and soaked for a while.

That was just what I needed. After I came back out I felt recharged. So did the kids. Off came the towel and they each fucked me again. At one point I was getting tired of being on my back so when Bruce switched with Scott I took one of your suggestions. I rolled over onto my side and lifted my leg into the air. It didn't take Bruce long to figure out how this position worked and he fucked me for a long time this way. I really enjoyed that a lot. Thank you for suggesting it.

About 10:00 they ordered another pizza. While we were waiting for it to be delivered to the room Tommy joked that I should "fuck the delivery guy". The other two were all for it, but I didn't think it was a good idea and I pleaded with Tommy not to make me do that. He finally relented but only on the condition that I answer the door in the nude and I let them fuck me up against the window later. Were were on the 5th floor but facing into a courtyard. If anybody on the other side of the hotel looked out their window they would be able see us, but that seemed like a safer alternative.

So when the knock on the door came, I peeked out first to verify who it was. There was what looked like a bored 18 year old standing there with a small cart. I opened the door wide and acted like I did this all the time. The kid just stared at my naked body for a second and then stammered something about me needing to sign for the pizzas. He handed me the card and I signed it. I handed the card back to him and he just stood the looking at me for a second. I was so embarrassed, but I tried not to let it show. Then he recovered his senses and handed me two pizzas. I took them, turned around, and closed the door with my butt.

The rest of the evening was more sucking and fucking. Like I said before, I couldn't believe how they could just keep getting it up. Tommy tried to fuck me standing up pressed against the window, but I was too short and he couldn't maintain the angle. In the end he had to settle for fondling me and getting his cock sucked in front of it. I'm pretty sure that we were watched by a couple on the other side of the court yard.

Sometime after 1:00AM we all fell asleep on the king bed. I think they each woke me up at least twice during the night to fuck me. I'm not sure, but I think I actually slept through a couple of them, I was so tired.

At about 9:00 or so I think (I'm a little fuzzy on the details here) I was woken up by Bruce as he pushed his cock into me. After he was done Tommy had his turn followed by Scott. Then I hit the shower. While I was in there Scott joined me saying that he always wanted to shower with a girl. We soaped each other up and generally got squeaky clean. It was actually a tender moment, which I really appreciated right then, but my concerns about Scott falling for me returned.

We checked out around 11:00, but I was still too tired to drive, so I asked Bruce to drive us back. I sacked out in the big rear seat with Tommy while Scott rode in front with Bruce. About half way there I was woken up by Tommy pulling my sweater up. He was trying to get it off of me and I helped him by putting my hands over my head. I was tired and didn't really care that we were in a moving car in broad daylight. I didn't even remember that I had not worn a bra until I felt Tommy playing with my boobs. It felt good, so I just let him do what he wanted while I dozed.

I must have fallen asleep because Tommy was shaking me and telling me that I needed to get dressed since we were almost "home". It took me a second to realize where I was. I looked around and saw that we were only a few miles out of town and I quickly pulled my sweater back on. "Those truckers really liked looking at your tits," Tommy says straight out.

I asked, "Truckers? Really?" Still not quite awake.

Tommy replied, "Oh yeah, lots of them."

I tried to think if I knew any truckers, but I wasn't sure. Maybe Joe did. I'll have to ask him sometime.

When we got back to the center the kids wanted to tell Joe all about the trip, but I was still dead tired and insisted that Joe drive me home. Joe told them that he would call them later. I got home and slept for about six hours before Joe woke me up to go out for dinner. He wanted to know all the details and asked a lot of questions. Next time I write I'll give you the highlights of those conversations.

I have to go now, but before I do I promised to tell you what the final count was for the Pittsburgh adventure. This is what I told Joe and is the best estimate I could make:

Anal sex: 2

Regular sex: 20 - 25

Oral sex: 15 - 20

Exposed to strangers: 1 hotel delivery boy, 1 couple across the court yard, and an unknown number of truckers

Orgasms for me: 10-12 (some were small and I may have missed a few)

Orgasms for the kids: 15 - 20

I know that the numbers don't add up (more sex than orgasms), but there were a lot of times when one of the kids would be fucking me and then would just switch with one of the others without cumming. After they came a few times they could go a long time before cumming again. I do know for sure that I swallowed four or five loads and took three on my face. Two were in my butt, so the rest was in my pussy.

Wait my phone is ringing.

That was Bruce, he is on his way over. I'll try to write some more later. I need to get you caught up so I can tell you about more recent events.


Apr 04/16/09 7:13PM


I was surprised to find another long email from you when I got home from work. WOW. I have a lot to think about, but I'll start with the notes I took from the first part of the Pittsburgh adventure.

I'm glad that Joe finally realized you need that uninterrupted time on the computer. Telling him that you were writing a journal was genius and pretty close to the truth. I'm really grateful that you are trying to catch me up on recent events. As I said before, I think maybe you have really turned a few important corners last weekend.

It sounds like Bruce is more the type that you are attracted to. That should make having sex with him a little hotter. From the way he acted I'd say he must have had more sexual experiences than the other boys. My guess is that he had a girlfriend at one point (and maybe still does) and they had a sexual relationship. I would love to know what he was thinking in that McDonalds. What were you feeling when you were kissing Tommy and Scott there in the restaurant? When the young mothers were giving you the evil eye, how did that make you feel?

In the hotel room when you described how they were kissing and fondling you after you were stripped, that was extremely hot! This is probably not a fair question but I'll ask anyway. How would you rate their cocks, from best to worst? Use any criteria you wish, just say how you decided.

It sounds like they were plenty vocal. I expect you are correct and that Joe has been pushing that. Bruce seemed to take to it easily enough, which surprised me a little. From what you wrote, though, you were not very vocal and were still mostly passive, except for the spanking. Is that a fair assessment? I really do think that Joe wants you to be a little less passive, so I'm glad to see you agree with me on that. I'll try to suggest simple ways that you can accomplish that. I know it won't be easy for you, but I believe that you can do it if you set your mind to it.

OK, just a few more questions. Was the anal sex as bad as you thought it would be? What were you thinking when you had to answer the door nude and sign the charge slip? Can you talk about the whole humiliation/embarrassment equals arousal thing? I'm pretty sure this was the most sex you've ever had in such a short period of time (around 20 hours?), but was it the most intense? Overall was it the best sex of your life? How would you describe it in a sentence?

Your friend,


Apr 04/16/09 9:34PM


I can answer some of your questions by telling you about my conversations with Joe on Saturday. The rest of them I'll answer at the end. If I miss any, just let me know.

As I said, I slept all Saturday afternoon. When Joe finally woke me up to get something to eat I was still tired, but I was also famished. I just threw my sweater and jeans back on that I had worn home from Pittsburgh and Joe took us to a little local place that we frequent. It is close to home and has good food. We took a small table in a corner so we could have some privacy.

Joe was interested in many of the same things you are and asked a lot of the same questions. It still amazes me how alike you two are. He asked me about the kissing in McDonald's too. I told him that I was embarrassed by it even though I enjoyed the kisses. He asked why I was embarrassed. I told him it was because the kids were so much younger than me. He said, "That's what made it so hot." I'll never figure you men out.

Joe thought that the young mothers were jealous of me "having three young studs" to "service" me. I think they were upset because they thought the heavy kissing was inappropriate in a family restaurant with children present. I told Joe that I felt a little ashamed to be caught kissing in there like that. What I couldn't tell him though, was that I also felt a little turned on at the same time. A lot of the things I've been doing lately are "naughty" and I think I'm starting to get hooked on it.

He also seemed to be very interested in the spanking, whether I enjoyed it or not. I told him it was OK (actually sort of fun) until Bruce and Scott started paddling me harder. He was also very interested in knowing what I was feeling when I had to beg for anal sex from Tommy and when I had to answer the door nude. In two words: humiliated and embarrassed. In fact there was quite a bit of that the entire time, but those two were probably the most intense.

That was as far as we got in the restaurant. When we got back home we went to bed and talked some more. In fact that's when we talked about the connection between humiliation, embarrassment, and sexual arousal. I'll tell you what I told Joe. I don't know what the connection is, only that it is there. It's like those feelings are wired directly into the pleasure center of my brain. I can't describe it any better.

Then I came up with the activity count that I already gave you. By this time Joe was hard and wanted to make love. He knew I was still sore and so he was very gentle and loving. It was just what I needed after the orgy in Pittsburgh.

You asked what I was thinking when I answered the door nude. As I was walking up to the door I was thinking "oh my god, I can't believe I'm going to do this". When I actually opened the door I was just trying to forget about the fact that I was nude. That wasn't easy. I tried to act like I was fully dressed and not nervous at all. I think I did a pretty good job, but I'm sure the delivery boy could tell I was embarrassed. You need to know something about me when I'm very embarrassed. I blush, but not just in my face. My neck and chest flush too and it's easy to see with my complexion. When the situation is sexual my nipples also stick out, and this time was no different. So I'm sure he could tell!

How would I rate their cocks? That is a difficult question. I guess that I liked Bruce's the best because it was just the right size for sucking and fucking. And he knew how to use it better than Tommy and Scott. It's a toss-up between the other two. Tommy's is better for sucking and Scott's is better for fucking.

Was that the most sex I'd had in a single day? Yes. Was it the most intense? No. One time with Jay an another man that worked at the office was more intense. I'll have to tell you about that some time. Overall was it the best sex of my life? It was definitely the most orgasms in one day, but also the only time I got sore muscles from having sex, not to mention my butt. So it was a mixed bag. I guess if I had to give you a yes or no answer, then yes, overall it was the best sex of my life. So far.

Tomorrow I have to work and then we are going out with Jeanne and Dick. I think Joe has something planned, but he's not saying what. So I probably won't be able to write you until Saturday. Then I'll finish telling you about the Easter surprise, as you put it (accurately) and the rest of the week, including Bruce's visit today. There's a lot to tell you, but I'm more determined than ever to get you caught up.


Apr 04/16/09 9:34PM


Thanks again for giving me so much to think about. Yes, Joe and I do seem to think a lot alike when it comes to this wife sharing, GB, submissive fantasy. Despite that he is still surprising me on a regular basis. I guess that's one of the things that keeps our conversations so fun.

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