Freaky Good Man

I finally got the chance to play with a friend that I had met over a year ago. We met in person at a party last summer. We flirted a bit but nothing was pursued from either of us. We did keep in touch and would check on each other from time to time.

The other day I saw her online and we started to chat and catch up with each other. She had been familiar with the blog, but she hadn’t really been keeping up with it so I told her to check out the latest updates.

After discussing what we had been doing since we last chatted and talking about the latest adventures on the blog. We decided to hook up but this time with the intentions of being very very bad. lol

We decided to hook up Saturday night and on Sunday we tentatively had planned to go to the swingers club. She had never been, but had read about my experiences on the blog. The reason I say Sunday was tentative is that I knew that it was a good chance that she may change her mind about going.

It was at the first part of the week when we decided to hook up, so it made for a long week with anticipation. During the week we chatted and talked some shit to each other. I tried to feel her out about what she was open to and was not open to which I think is so important. If you know that you can let it all hang out with a person, you can just go for broke. It is also important to know what that person is not into, so you don’t push the wrong button to turn that person off.

She gave me the green light on everything except cumming in her mouth. Now cumming in a woman’s mouth is one of my favorites, but I have a big two that I like. If I can get at least one of the big two I am cool. Now it doesn’t mean that I have to do the big 2, but to know that if I am in the mood for them that I can go there is great. The big two are cumming in the woman’s mouth and of course anal sex. Now when I say the big two, they are two of the things that I enjoy that there is a very good chance a woman may not be down with. They are still on the Taboo list for a lot of women. So no cumming in the mouth, but anal was a GO.

Saturday night comes and I get us a hotel room. She meets me and we get comfy in the room. We are lying on the bed getting mellow and having convo. She starts rubbing my dick and then leans over and starts to suck it. She has great head skills and is going to work. As she is sucking it, the YM is hard, but it’s not that superman hard. I grab the YM and start stroking it while she is sucking it and it got superman hard and was fully inflated. lol I pull the YM out of her mouth and start slapping her on the face and tongue with it. When it got fully loaded, she kind of sat back and looked and was like damn.

After about 10 mins of sucking me I had to make her stop. It was feeling great and I was close to cumming. We had talked too much shit for me to be cumming that damn soon. So, I tell her to stop and told her that I wanted to eat her pussy. I start eating the pussy and she is cumming in no time. Her first orgasm was within 5 minutes of me eating her. She started running a bit, but I grabbed her legs and went to work on her. It was great!

Since she gave me pretty much free reign on what I could do to her, I brought my bag with a few toys in it. In fact I picked up a new gadget to play with that night. I bought a bondage set that I had seen a few months back. The package included 2 sets of nylon cuffs with Velcro straps, 2 tethers and a blindfold. For those of you that aren’t familiar, the tethers are used to strap the person cuff to cuff or cuff to something else. It basically allows you to secure the person however you want.

The first thing I do is blindfolded her. Then I cuffed her hands behind her back. After I do that, I make her bend over. Then I slide the wonderful silver bullet into her ass. Once I turned it on, she was done. She started cumming from the silver bullet in her ass before I could finish putting the other cuffs around her ankles. That silver bullet is a MF.

I started to kiss her and suck on her breast while she was standing there blindfolded with the silver bullet in her ass. I kissed her neck, sucked her nipples and played with her clit. She was so damn wet.

Then I made her bend over and entered her pussy from the back. She was so damn wet it slide in with no problem. I was fucking her from the back getting some nice deep strokes. I can tell she works the kitty because she would squeeze down on it from time to time and it felt so damn tight when she did that it was crazy. She came on the dick several times fucking that way. I was in a nice groove hitting the pussy nice and deep. She exploded with a huge orgasm and fell to the floor. It was so intense it was like someone had hit her in the stomach or something.

After she recouped a bit from that orgasm. I unhooked the handcuffs that were on her hands. The cuffs were still on her wrist, just not connected. Once I did that, I laid her down on the bed and ate her pussy. Then I started fucking her missionary style. I always like to lick the pussy before changing positions. When we did it missionary I would spread her legs wide and also put them on my shoulders. I was getting some nice long strokes in.

After doing missionary for a while we took a short break. After the break she came over and started to ride the dick. At first she was grinding me with the dick in the pussy. It was feeling great but I wanted to get in her as deep as I could so I made her put her feet flat on the bed and I slid my hands underneath her ass and started bouncing her up and down on my dick. It was getting so deep in her she started cumming hard again and was moaning very loud. Every time it was time for her to come down on the dick I would slam her back down so it would get in deep.

She asked me to switch back to doggy style and I said ok, but it started feeling so damn good with her riding, I reached up with one hand and started to choke her. I told her she couldn’t get off that dick yet. As I was choking her, I was telling her she “better bounce on this fucking dick”. I told her she better not fucking stop riding. She was cumming all over my dick.

We switched positions and got back to doggy style, more a standing doggy. Where she is on her feet but bending over taking it from the back. I am grabbing her hips and just going to work on her pussy. I start to spank her ass. Nice firm stinging spanks. She loved every spank. I started pulling her hair while I was fucking her doggy. I grabbed her hair enough to use it to pull her back into my dick. I would also grab her shoulders and pull her back to me to get in deep. We fucked like that for a long time. It was just feeling so good and she just kept cumming. She eventually collapses on the ground again and put her face into the mattress. I didn’t realize it until she told me later, but at that point she started crying tears of joy. She was trying to hide it from me.

She was pretty much spent but she had agreed to let me do her anally and we had not gotten to that yet. So I asked her if she was still willing and after a short break she was down. When she stood back up, there was cum all over her thighs from her cumming so much.

At the start of the night when she started giving me head, I was fingering her pussy and her ass. Her ass felt very tight and I wasn’t sure if we would be able to make it work. We pulled out her lube and my vibrator. I bent her over and gently started working the vibrator in. After a little work I was able to get most of it in and started working it in and out of her ass. Next thing you know she cums on the vibrator. At that point you know I am ready to get the YM into the mix.

I asked her if she was comfortable and ready to try. She said yes, so I put lube on me and put more on her. Her cumming on the vibrator loosened her ass up nicely. I was able to get in without much of a problem. I took my time and eventually got about 85% inside her ass. It felt so damn good and so tight. I was able to start to stroke her ass pretty good, but not full force. I was spanking her ass as I fucked it and she loved it every time I spanked her. She ended up cumming about 3 times from anal. It felt so damn good.

After I did her in the ass I switched condoms and started fucking her again doggy. I was fucking her so good, she kept cumming over and over. We stayed in that position for a long time. I would spank her ass, I would pull her hair, and she would squeeze that pussy so hard. It was like a heavy weight fight. lol After awhile I asked her if I could cum, we had fucked so long I thought she would say yes. So I started releasing my cum before I got the answer and she said NO. So I had to try to pull back from cumming, but could only hold back another 5 mins. and shot a big load of cum all over her ass. It felt so damn good to cum.

We fucked so long it was crazy. The YM was in tiptop form. It would have been a great night for a 3some because I had enough to go around. She said the most she had cum before was 16 times. We went into the encounter trying to beat her record, well at least I did. lol You know how competitive I am. So, I made her tell me every time she came. The last time we remember was somewhere around 25 and we lost count. When we were at that point, I was shooting for doubling her previous orgasm record. I think we got there, but again we both lost count.

It was such an explosive session that when she left the hotel that night / early morning and was talking to me on the ride home. She had another orgasm just driving and talking to me. It was crazy. She was talking and all of a sudden was like damn I am about to cum again. Now that’s some good shit.

The next night we did hook up and got to the swingers club. We had a pretty good time, but we just played with each other. The crowd was a little light and most of the people were playing in private rooms. We went into a private room ourselves and got some good doggy style in. Her kitty was sore from the previous night, but it was all good. She did suck my dick out in the pool and hot tub area.

She told me later that she had squirted. As much as she was cumming I was expecting her to, because she had some pretty intense orgasms. For some reason I missed it. But it would explain the serious amount of cum that was coming down her legs.