My Second Time

Sade has suggested I write about some of my earlier experiences in my submission. I realized there were a number I’ve never even told her about. Not because I was hiding anything but because it just never came up in conversation..also all of these experiences pale in comparison to the countless experiences I’ve had with her. It would be like winning the lottery and still talking about that time you won $50 at your monthly poker game.

Still, she asked for some earlier stories….and here’s one.  My second time playing with a dominant woman:

In my mid-twenties I was still living in the midwest, I was on a few kinky dating sites but there were really only a few dominant women in my area…ok..in my state. I was pretty much just having casual relationships with a few vanilla women at the time but nothing serious and certainly nothing kinky.

One day I had an email from a woman who had looked at one of my profiles. We started emailing back and forth and she made herself pretty clear of what she wanted. Right off the bat she wanted me to know there would never be any sex between us. I told her I understood and promised not to push the issue. We talked on the phone and she had me send her naked photos of myself, mostly of me on my knees. She also expressed interest in the vanilla women I was sleeping with at the time.

She had never done anything like this before, she was in her late 30’s and being dominant was something she needed to “get out of her system”. Since I was usually done with work by noon every day it was perfect for her. She said I’d usually be coming over in the early afternoons.

I realize now it was pretty stupid of me to not even ask what she wanted of me, or what she was even into. I didn’t even ask to meet in a public place beforehand. I had only submitted to one person before her and my eagerness and inexperience overwhelmed any rational thought. A few days later I found myself driving over to her place.

She lived in a wealthier part of town in a huge house. For some reason this made me even more nervous as I pulled up.

She greeted me at the door and was very friendly. I remember thinking she wasn’t acting anything like I imagined. She was so friendly and relaxed it was almost like I was just coming over to have a cup of coffee with a new neighbor. Maybe she was trying to put my mind at ease since she could tell I was extremely nervous.

We talked for a few more minutes and eventually she took me to her living room, stood me in the center, put a blindfold on me and told me to wait there. I stood there for maybe five minutes while I heard her walking around upstairs. It was at this point I realized I had no idea what I was in for and this really turned me on.

She came back in the room and her tone was completely different. She was still friendly but now she was a bit more stern. She ordered me to strip and made me hand her each article of clothing as I took them off. Then she had me kneel on a towel with my knees spread wide and poured baby oil all over my erection. I heard her sit on the couch about ten feet away from me and ordered me to jerk off but not to orgasm without permission.

I had never experienced edging before. She made me get as close to orgasm as possible and then had me stop everything and let go for a minute or two before continuing. The whole time I could hear her panting and masturbating herself while directing me now and then she’d take photos.

During those breaks when I wasn’t stroking myself she’d always make comments:

-“Look at that hungry cock, how many nice girls did you feed it this week?”

-“You’re being such a good boy but I bet you really want to fuck me with that cock don’t you?”

-“Your nice girls have no ideas you’d rather be jerking off here for me than fucking them.”

-“You’re being such a good slutboy for me.”

After about an hour she made me come on my chest and just kneel there for a few minutes so she could look at me and had me put my clothes on my messy body while she left the room. Eventually she came back in and took the blindfold off and was back to her friendly self saying how lovely it was (I specifically remember the word “lovely” and how it seemed out of place) and wanted me to come over again soon but I wasn’t to ever contact her, she would contact me and I was to never ask her about her life other than basic pleasantries.

So it became something we’d do once or twice a month. I wouldn’t hear from her for weeks then I’d get a very short email asking if I was free that day and I’d come over and jerk off for her. Usually she’d make me stay there quietly blindfolded while she handled work calls and then she’d make me do it again. I always had the blindfold on.

I felt so objectified and desired. I craved it, wanted to be objectified and used more and more.

Every time I came over she’d up the ante on what she wanted me to do. Once she had me lay on some plastic sheet of some kind, covered in baby oil and made me fuck the floor so she could watch my ass, the whole time saying she wanted to see how I’d fuck her if she let me.

It was very rare that she’d ever touch me so when she did it was a big jolt for me. I remember her holding my ankle so she could tie it to the leg of the couch on one side of the room and then held the other so she could tie it to the couch on the other side of the room and spread my legs as wide as they could go. Each time she touched my ankle I was moaning since I rarely felt her touch.

The first time I experienced anal play was when she had me jerking off on all fours and she slid a thin vibrator in my ass and started spanking me. Then she made me get on my back and fuck myself with it and I could hear her use a vibrator on herself. I think it’s because of her that I wasn’t ashamed of enjoying anal play because she kept moaning how hot she thought I looked doing it. Had she made fun of me or tried humiliation with it I probably would have associated a negative feeling toward anal play.

We played maybe 10 times. The last time we played I didn’t know it was the last time. Everything was normal at first but this time she made me edge myself for much longer than usual, plus she was sitting closer to me on the floor instead of on the couch. I could hear her masturbating and at one point she shoved her foot in my mouth, making me suck on it while she came. I didn’t have a foot fetish but this really pushed me and I found it hard not to come since I was dying to have any part of her in my mouth.

After she came down from her orgasm she handcuffed me to the leg of the couch and just watched me laying there, hard and desperate. Then she sat on my face had had me eat her out. It was the first time I ever came in direct sexual contact with her. I don’t know how many times she came but eventually she had to get up and get some water.

When she came back she took the blindfold off and told me she always wanted a man to lick her asshole and asked if I would. Of course I agreed and she had me lick her while she masturbated. After she came she fell forward and surprised me by taking me in her mouth. We 69’ed for a few minutes. She kept saying how she always wanted to do it to me but just couldn’t. I didn’t understand what she meant at the time but I would eventually find out.

After she came again from sitting on me she took me out of her mouth and told me she was going to give me something special. She lubed up a vibrator with baby oil an slid it inside me while she stroked me. I was so close to orgasm but she was moving so slowly that I didn’t think it would happen. This went on forever., the vibrator slowly sliding inside me while she was slowly stroking me up and down.

Out of nowhere she picked up the pace of the vibrator so it was slamming into me but she was holding on to my cock without moving it then she went from 0 – 10000mph with her stroking and as I started to come she slid her mouth over me and sucked.

I think I blacked out.

I remember going home, excited that things were progressing to a whole new level. I couldn’t believe how good it felt to be objectified so much. To be used like that. I was so excited. When I got home though she sent me a long email saying she was leaving town in a few days. She was married and her husband moved months ago and they were just waiting until they found a house for her to move there with him. He was very vanilla and had no interest in her dominant desires but she loved him and would never leave him. She said she didn’t mean for it to go as far as it did but she couldn’t help herself since she knew it would be the last time she could see me.

I was crushed and she knew it. I replied back asking if we could play again before she left. She had to refuse, saying she knew it would only go further and she couldn’t do that to her husband. She said she was too old for me anyway and
said I needed to stop leading vanilla girls on and I needed to find a dominant woman, that I was a slave and she could tell this was a very deep part of me. She said I was a good boy and that I should never contact her again since it would just make things hard for both of us. I agreed and didn’t contact her again.

A year or so later I got an email from her. In the subject line it said “Do not reply to this email” The text only said “I miss this slutboy” There was a photo attachment of me on my knees jerking off.