Freaky Good Man

The wedding present.

There was a female I met while staying at my condo that was pretty cool. She had recently gotten engaged and was a few months away from moving to New Jersey to be with her husband to be. After she had gotten engaged she still wanted to play. I told her I wasn’t comfortable with it and that we wouldn’t play anymore. She wasn’t very happy about it, but rolled with the punches. We would communicate every so often just to catch up. The closer she came to leaving the more frequent she would bring up having one last play session. She switched gears and said that she had told her fiancée about me and because he was a bit older than her he was ok with her having a little fun until she got to New Jersey. She went as far as having general conversation with me when he was in the car with her and even giving him the phone so we could have general conversation. Now this conversation had nothing to do with the two of us playing, but I think she was trying to convince me that she has been open and honest with him.

We have this long conversation about some of the things she really wanted to try before she became official and it was some pretty good stuff. Some of it was more fantasy in the mind type scenarios, but I think if it could have been set up in the right way she would have went for it. One of the things she told me that she really wanted to try was being fisted. For those of you who have been reading me for awhile, I have had an experience attempting to fist a woman and have been open to experiencing it again. Needless to say, we ended up setting a play session up.

When she gets to my place she has this silver briefcase that looks like something out of James Bond. The shit had a lock and a combination code on it. Turns out those were all of her toys which she actually kept in her car for safe keeping away from her family. Shit was hilarious. She opened that thing up and had a mini arsenal of toys in there.

She had planned to spend the night so we took our time getting down to business. After walking to a restaurant near by and having several drinks after we got back, I could tell she had relaxed a bit. Although she was doing most of the chasing she was nervous as hell to the point it she was visibly nervous.

She jumped in the shower while I was watching a game on TV. She came out in bra and panties looking very sexy. This is not a big deal, but in the living room area of my condo the window was wide open with no blinds or curtains. Now I was on the 18th floor, so not like just anybody could see in, but you never know.

She comes over and sits on the floor between my legs and starts rubbing her hand all over my dick. Then she just pulls it out and goes to town giving me head. She attacked the dick like she was hungry. I slowed her down a little and put my hand behind her head to hold it down so she could deep throat. She tried to take it like a champ and got most of it in. Very nice job. It was a nice wet head job, but not too sloppy. After about 10 mins of some very nice head we move to my bed room.

In my bedroom, I have a king size bed and room for my futon. My futon is one of my secret weapons because it’s firm, some what low to the ground and most importantly it’s frame is made of metal and has several was that you can attach bondage straps to it. 

Part of the agreement that I made with her, was that if I agreed to a session I would get to do whatever I wanted to her. She agreed.

She gets completely naked and I lay her on the futon and thing bring out my ankle and hand cuffs. These cuffs are the cloth type with Velcro to keep them secure. They are very sturdy but are a lot more comfortable than regular cuffs. They also have little hooks on them so you can make addition attachments. I had already positioned the tie downs on the futon before she had gotten there. So once I had her cuffed it was on.

I cuffed her left wrist and ankle together and did the same for the right side. I then hooked each side to a separate tie down so that she was spread eagle. I took my time and started playing with her body. Lightly pinching her nipples and sucking on them. I stared kissing her neck and whispered to her to see if she was comfortable. She said that she was, but she was breathing very heavy with anticipation. I start to finger her pussy and she was wet as hell. I knew we were in for a fun time.

After fingering her and getting her to start moaning a bit I drop down to my knees and started eating her pussy. Her legs started to tighten up and she was moaning so damn loud. My dick got so hard hearing her and seeing her at my mercy. Her legs were trying to close as she was about to cum, but the bondage straps were doing their job nicely. Her back stared arching and lifted her ass off the futon, but I was there step for step eating that pussy like I was riding a wild horse. Next thing you know she is screaming oh shit and her body releases that nut as she breaks down in convulsions.

I really wanted to put on a condom right then and start fucking her, but I wanted to try the fisting first. I grab the lube and start to lube her pussy and my hand. I was able to get 3 fingers in pretty easily and started to be more aggressive fingering her pussy. She loved it. The fourth finger when in with a little work, but no major problem. I start rubbing her clit and she started cumming again with my four fingers insider her. That was actually not very good, because it made her pussy tighten up from cumming. After she relaxed for a few minutes I added more lube and got back to working her pussy. She was so damn wet from the lube and her natural juices I had to put a towel under her. Once she got back really relaxed and enjoying me I was able to get 5 full fingers in and most of my knuckles in. I could tell I was getting close to her limit, but as I checked on her she said she was still ok and it she said it felt real good.

We took a short break and I decided to take the cuffs off of her to see if she could relax more. We started back with me lightly sucking on her clit. I also pulled out one of my bullets and slid it in her ass to see if the attention on the bullet in her ass would possibly allow her to take the rest of my hand. She loved the feel of the bullet in her ass and was ready to go for more of my hand. I get back to my all of my finger in her and was able to get pass all of my knuckles and then she started to panic on me. It was a very hot visual, pretty much my whole hand was inside her pussy, but you could still see the bottom of my palm. I could tell as I pushed in that I was stretching her some, but it really felt like it was going to go in any moment. But, I was responding to her and would back off when it seemed like it hurt. With her not being tied up, she started moving a lot more and it made it more difficult to go all the way. We finally came to a stopping point, literally an inch or so from reaching our goal. When I asked her about trying more, she said that in her mind she had lost the mental of being able to do it and it was over riding her wanting to get it done. She said that she didn’t realize how close I was until I showed her how far of my hand was inside her. After showing her that, she felt that she good have gotten over that last hump. Unfortunately we didn’t get back to that.

That was not the end of the story however. She has a great body with a very sexy ass. So, I asked if she was willing to try anal earlier in the night and she agreed to it. She said she had done it before but it had been years and that she had never reached an orgasm from anal before. You know, me challenge and goal number one was to see if I could make her cum from anal.

She said she had actually came a couple of times while I was trying to fist her and while the bullet was in her ass so her ass was ready for some action. I put on a condom and lube her ass while she is in doggystyle. I slowly work my dick into her ass and it felt so damn tight and good. I tell her to rub her clit while I was inching inside of her ass with easy but firm strokes trying to get deeper into her. After a few minutes she started working her ass and moaning louder and louder. I told her to tell me where my dick was and as she kept saying it’s in my ass she started pushing back on my dick as her ass opened up. I started spanking her ass and then grabbed her hips and started fucking her in the ass with some nice deep strokes. Next thing I know she starts clamping down hard on my dick and starts saying: “Oh fuck, Oh fuck I am cumming”. She lets out a deep moan and her upper body collapses onto the bed.

I still had both hand on her hips and after a short pause started to slowly continue to fuck her. As she got over the orgasm she got back to bring that ass back on to the dick. I fucked her ass for a good 15 to 20 mins until I told her I was about to cum and I exploded a nut inside her ass (with condom on). She turned around as I pulled the condom off and sucked all of the cum off of my dick. After she cleaned my dick off she fell to her side and was literally snoring in a fetal position in about 5 minutes. I grabbed a blanked and put it on top of her. I went to wash up and finished watching whatever game was on TV.

After about an hour nap, she came out to the living room and specifically asked if I would fuck her in the ass again. I initially thought she was talking about at some other time and she was like, no I want it again right now. I was more than happy to oblige the request. I did fuck her pussy before I got back into her ass this time, but we had a nice 30 min session to end the night. We both passed out and had a good night sleep after the second session.

My friend has since moved to New Jersey and has said she has been faithful to her now husband. But, she did email one day saying she was having all of these freaky thoughts. She also let me know that she would be in town soon and I told her that she had to hold on to the memory and enjoy my wedding present to her.