Things were a little awkward at first, so we started slow by just kissing with some heavy petting. Once I felt comfortable, The T and I got naked. I had never put on a condom before, so he had me do it. I fumbled a bit, but finally I got it.

I wasn’t really wet enough, so he decided to go down on me. It felt good, but not quite good enough. Luckily though, that made me wet enough. He slid his cock in slowly, riding on top of me. We kept this position for a bit, until he wanted to fuck me doggy style.

I had a problem keeping my ass higher than my head, but eventually we had the right position. We decided to get the bullet out, to try and make me cum. That is when Leah came in to join us. Before I got the bullet onto my now dripping wet pussy, she asked to go down on me. I said sure, and opened my legs once more.

Unfortunately, she did not last long down there because all she could taste was condom lube. I did not blame her one bit, so I went down on her instead. She was the first girl I went down on, and I hope she won’t be the last. I did just as I had always imagined myself doing with a girl, and slowly traced my tongue all along the pussy lips, then around the clit. She moaned, telling me I was doing it just right, but it would not make her cum. She had me stop so that The T and I could continue and she could use her vibrator.

The T had me put on a fresh condom and told me to climb on top. It was my first time on top, so the positioning was very awkward at first. Eventually I had a good hythm going, where I gripped the top of the head board and he used his hips to move me up and down. Sadly, just when I was really enjoying that position, I got a bad cramp in my hip, so we switched to him on top.

This time I had my bullet ready, and I got it on my clit while he fucked me. Leah stopped what she was doing with her vibe to encourage me to cum.

“Oh God, Leah, shes so close, shes so tight,” The T moaned.

“Ooo, I can tell shes close, by her breathing,” Leah said.

The truth was, I was close, but not close enough. The pressure of needing to cum was building, physically and emotionally. Unfortunately, the emotional pressure to cum outweighed the physical. Leah was so excited that I was gonna cum, I could not disappoint her. I started making the sounds I make when orgasming, and flexing my pussy around The T’s cock. They both encouraged me while I was cumming, and talking dirty to me. After a few seconds, I slowed down on the moaning and relaxed.
After I “came,” Leah went back to the living room to watch another show of hers. Once she was out of hearing distance, The T asked the dreaded question.

“You didn’t really finish, did you?”

I decided to be honest. “No, she was pressuring me so much I just couldn’t. I lost the closeness I had to cumming,” I said to him quietly.

“I understand completely, and thank you for being honest,” he said back.

That was the only time I faked my orgasm. I never really saw the point in faking. I think that if you fake an orgasm with someone, they think they are doing something right, and will never really know how to get you off. The only reason I faked this time was to not disappoint my hostess, who I knew we would never be hooking up again. I was glad The T was so understanding.

We ended up putting on a fresh condom so that he could at least have his orgasm. Leah was right, it was good sex with him. It was easy to turn down Toby after fucking The T. The T and I never got together again, unfortunately, because Leah decided she did not want to share him anymore. She was apparently jealous to see me fucking her “best friend.”

I told her thats great, but I don’t know anyone else that will have sex with me. She told me about The T. The T was one of her close friends, and knew how to pleasure a woman. He could not get off unless she got off. She also said she was willing to host us, and that we could stay over at her place.

A few nights later, I went over to her place to meet The T. He seemed nice, but I wasn’t quite comfortable enough to do anything sexual. We did kiss a bit, and I have to say, it was not bad. I was horny, but not ready. He understood and respected that, so we decided to try for next time.

The next time the three of us got together, we made a safeword (tricycle). We also planned how we would do things (her room, her bed, she would come in and watch once in a while, maybe join in). She asked me if he could fuck her too, or just me. I preferred that he just fuck me. She was fine with that.

I went home to get my bag of goodies (something sexy to wear, bullet, and strap on with Raquel), and told my mom that I was going to stay next door for the night.

To be continued…

I know a lot of people use words like “orange” or “red” as their safeword. I am not sure how we came up with tricycle. I think it was just the fact that there were three of us, and we were trying to find random words that were unique enough to remember in the heat of the moment.

Our safeword never got used, but it sure did get made fun of. It became our inside joke when one of us would come up to the other (two) and say “I want to ride your tricycle.” No one knew what the hell we were talking about, it was great.

I got into this habit with Will. Since Will was not a very sexual person, I would thank him anytime things got sexual. I would even thank him when I did all the work (by sucking him off).

At first he seemed really turned off by me thanking him, feeling like he was abusing me (he actually said it like that). I explained that this was not the case at all, and that the reason I thanked him was because I wanted to show my appreciation for his sexual mood. He accepted that explanation, and began to thank me afterwards as well.

Even after Will I still thank my partner for sexual encounters. The two times I got with Toby after the break up I ended up thanking him. He thought he was king shit afterwards. With him, it was definitely not the case. It was just a habit, me thanking him.

However, when I got with D, it was definitely more than habit. I really was truly thankful that I had another chance to get with him, and glad that we weren’t as limited as we were the first time we hooked up in the woods outside our school.

After a couple times of saying “thanks,” he said that I didn’t have to thank him. I ended up apologizing, and explained the habit. We left it at that.

So really, I don’t know if this is a good or bad habit. It is polite at least, but I am not sure if its something I should break myself of or what. I really don’t mind thanking the other person for sex, but I certainly don’t thank myself for masturbating. That might be pushing the weirdness a bit.

I led him to my bed, where he first took off my shirt, then my pants and thong. As I was getting out a condom from my stash under my bed, he ended up getting the rest of his clothes off. I admired his body by running my hand over his chest, then taking his cock in my hands to put the condom on.

Once the condom was on, I scooted back onto my bed, where he climbed on top of my, guiding his cock into my ready pussy. I asked if I needed lube, as I wasn’t sure how wet I was.

“What do you think?” he asked, as he slid deeper inside, my wetness very audible.

“Ahh, I guess not,” I said, smiling.

He started with slow thrusts, then getting faster and deeper. He kept a very steady rhythm, only slowing down a few times to pace himself. Eventually though, he had to cum. He gave one last deep, slow thrust, then reaching himself forward to kiss me.

“Thank you,” he said, smiling.

“You’re very welcome, and thank you,” I said, grinning back.

The other night at work, the idea of doing that again has been a real turn on. I think I will have to get it out again and do just that. There will definitely be an update.

Because I don’t like the idea of hearing my name during sex, I have never called anyone else’s name out. Now, I don’t know if people really do this normally. I am sure some people get extremely turned on by it, but it could also be just something in the movies. I am not really experienced enough to know.

I know a few years ago I ended up “accidentally” watch my friends have sex on webcam. They tricked me into it really. We were just casually chatting, and the next thing I knew they were having sex, and she was calling him “Daddy.” The camera was placed so that it only showed from the waist up, and she was wearing a shirt. They still give me shit for watching, but hey, they started it, and I was a little curious, and only slightly disappointed that I didn’t really see anything.

Despite all this, there have been several times that while masturbating, I have quietly called out the name of the person I was thinking of. The first time I did this, Will was at work and we were still at work. I felt very weird doing it, but I tried it.

The other time I did this, I ended up calling out (quietly), D’s name. I just said it over and over before and during my orgasm. It may have just been me, but the orgasm seemed slightly more intense than usual, but not much because I had been at it for a while with dying batteries.

I am considering trying to clear my mindset of not being turned off by hearing my name, and maybe not be so creeped out by calling someone else’s name. Is it normal to call out the person’s name you are fucking or thinking about while masturbating?

The first time I placed an ad, I would only give my picture when I received one myself. The problem was that once they saw the picture I sent (of my face) each and every responder quit responding. I guess I wasn’t pretty or skinny enough for them. The only real creeper I got was someone messaging me, telling they were married and wanted to know if i would be their “on the side.” Hell no, I don’t want to be involved in that crap.

The second time I placed the ad, I got twice as many responses. There were actually several people I had ongoing conversations with, one of them lasting about 6 hours through email. The other few lasted off and on for a couple days. However, once they all got my picture, they never wrote back. My low self esteem was not surprised.

One guy actually made plans to meet up with me for coffee, but then when I sent my picture so that he would know who to look for, he cancelled the day of the plan to meet. At least he was decent enough to let me know he wouldn’t be there, rather than me waste my gas to go to the damn coffee shop. His excuse? He had to babysit his brother.

There were some guys that seemed really promising, until they either turned out to be shallow or creepy. Both were expected, obviously. I really was not surprised that once people saw me, they quit talking to me. Though I was kind of irritated because I did say that I was a bigger girl in the ad. Either they didn’t see that part, or didn’t think I was THAT big.

One guy who seemed to be really promising showed his creepy side on the second email when I asked him what he did in his spare time. His response? “I like getting head.” That was all he wrote. I never did write back to him.

Out of all the emails, only one seemed to be a bot. At first I thought he was real, real creepy, until I started getting a bunch of links in the emails.

Out of all the guys that saw my picture, only one said that I was “gorgeous.” Unfortunately, he kept sending that same thing. He sent his pic, and he turned out to be one of the tweekers where I work. I quit responding to him as well, but he didn’t get the hint and kept emailing me. He has finally stopped, and has not recognized me at the casino.

I don’t know if I will post on there again, but if I do, maybe I should put it in bold that I am fat? Maybe then they won’t waste my time or theirs.

Orgasms have always relaxed me completely, however, there will be times (not very often as of lately) that I will fall asleep with my bullet in hand after an orgasm, wake up, and go for another masturbatory round. The more I masturbate in one session, the weaker the orgasm becomes. However, the longer I can keep the same orgasm going, the stronger it becomes, and the more likely I am to squirt (which I have not done in two years I think).

The last few times I have masturbated I have gotten very distracted. I think this happens because I wasn’t much in the horny mindset in the first place, and was just doing it to sleep, or as recently, take my pain away from my nipples. I was trying my hardest to think dirty thoughts, but then the stress of moving came into mind, then family after that (as I will be closer to them), and it just went downhill from there.

I then tried turning to my backup dirty thoughts, the ones that are/were a sure-fire way to get me off. Thoughts about Will, and things about him/us that got me off. Sure, they worked, but they made me feel sad. You see, for the two years we were together, he was all I could think about while masturbating. Nothing else really turned me on. Since the break up, I have had to reprogram my turn-ons. I try and think of anything but him, however, the more I try not to think of him, the more I do.

Most of the time thinking about other things help. Sometiems I pop in a porn on my dvd player, but its just not the same to me anymore. Lately I have been thinking about when D and I get together, and how turned on he makes me once we decide to get down to business. I like having sex with D, and I look forward to more sex with him.

I always used to feel creepy thinking about people I know in real life while masturbating. It just didn’t feel right. However, once I became sexually active, that kind of changed. I think it changed when I started this blog, really. This blog has really helped to give me an outlet to discover myself. Now I can think about people in real life while I masturbate, and write about it. I can’t however, think about people I have never done anything with though. I still feel creepy. I also feel creepy if I think about them when we no longer do things. Will and Forbidden Fruit are a good example of that.