Meeting Sydney

After my work trip, I didn't return back to Boston back when back to where I was living since I was still in the process of moving and sorting out my affairs at home. I thought about my time with Sydney that it was wrong to fool around with someone at work but also at the same time it was some of the best sex I had in a while. On Sunday I received a company message from Sydney if we can talk about a media message that needed to go on Monday, and I agreed. I gave her my cell and she called, she wanted to be careful, she thought she had my right cell to text but wanted to be professional I respected that. She said she wanted to see me again when I returned to Boston, she wasn't looking for anything serious but the sex between us was amazing and we should deny this, let's just be fuck buddies for now and see where it goes. I was happy to hear this and agreed with plans to hook up on Monday night.

I returned to Boston the next day and work was normal, Sydney and I agreed the night before to meet in my hotel that night where we would have room service followed by amazing sex which we had. This routine went on all week until I went home Friday for the weekend again. The following week though instead of my hotel I stayed at her place for the week, and somehow the sex got even better. One particular night I went after work with some people for drinks and returned to her place drunk, she got me in the shower to clean off and then into the bed where I just laid there. She proceeded to give me a blow job that normally I would not remember that well but after a couple of minutes, I felt her tongue on my ass followed by a finger that caused me to get harder and cum fast and then pass out.

The next day I had to think if this was real or not, as we didn't talk about it, I was too embarrassed to bring it up and she used the opportunity I believe to do this while I was drunk, little did she know I loved it.

It was a week later and again I was staying at her place and we were putting some of my clothes in her closet. One of the items fell on a box in a corner and when I picked it up I removed something covering the box to show some items in there, some sex toys, with one of the items being a strapon. Sydney look at me and I just said grinned and said interesting toys. She grabbed my cock they the shorts I had on and got on her knees saying they were and then gave me a blow job, that ended up in bed with a great sex session.

After that sex, we were just laying there I brought up the elephant in the room and asked was she Bi, she said yes but that is not what the toys were for. She then went on to tell me that years ago a boyfriend introduced her to pegging him. This led to her being dominant in the relationship acting as a dominatrix which she loved. They would break up because he wanted to be in a gay relationship. She said over the years she would date guys and try to introduce this sometimes it would work and then after a bit, they would break up, or it scared guys away, she was not looking for this anymore. She asked did this freak me out and I assured her it did not deep inside it turned me on a lot, but I was too nervous to say anything to her.

That weekend I went home and I was obsessed with porn videos of pegging and dominatrix. The following week was normal with Sydney but I kept thinking about what she told me and deep down wanted to tell her I was into it but finally, I did. All week it drove me crazy so on Friday morning I sent Sydney a text and said I decided to stay in town for the weekend do you have plans and want to see me. She quickly replied and said she would love to be with me all weekend. It was then at sent the text that would change our relationship, I said I was thinking we try something new, and she said what's that, and I replied remember what you said last week what you were into. She replied back with a yes, and I said I am into that, her reply back was are you serious! and I said yes have done before very into it, was nervous to say anything. She then replied back and said how far can we go tonight, I thought about this for a couple of minutes and just replied back we need to be discreet still, she then replied back be at my place at 6:30 then.

The rest of the day was hard to work on what was in store for us will this be the same as I experienced in the past, better will this bring us closer.

I got to her place at 6:30 and she was there as normal, she gave me a kiss and asked was serious and ready to submit to her, I kissed her with passion and told her, yes and I trusted her. She then said good, go into the room take a shower then come back to the bedroom and put on what she would put on the bed, no exceptions, and obey every command tonight. We kissed again and I disappeared into the bathroom to shower, when I came out she placed items on the bed but was not in there. I looked at the items and admittedly had 2nd thoughts but they quickly went away and I proceeded to put on the items. Thigh-high stockings, panties, bra, a collar around my neck, ball-gag, and a blindfold. I stood there for a couple of minutes feeling like a fool until I heard her come in, she didn't say anything but she secured my hands attached a leash to the collar, and told me to get on all fours a crawl as she led me out the room to the main area.

She then guided me onto a device where my legs were secured, my hands were free but then secured to the device, I would later find out I was attached to a bench she had for these occasions. Once I was totally secured she removed my blindfold, and she appeared in front of me, and once my eyes adjusted she looked hot as hell in a leather dominatrix outfit. She then asked was this what I am into as she removed the ball gag, and I said yes. She then asked me to tell her what I have done, I told her everything, which led her to ask if I have had BI sex and I admitted, she then put the gag back in my mouth.

She then went on to say that she picked up on vibes I might have been a fag for a while and a couple of weeks ago she started by fingering my ass when I was drunk and she could tell how much I liked it, you were so drunk you were begging for it, I didn't recall that. Then her next step was letting me see her toys by mistake to see if I would take it to the next step once she told me what she was into. And now I just admitted to sucking cock before and taking cock in the ass from women and men in the past. and on top of that here you are dressed like a fag, admitting this all to me and basically giving me the rights to own you.

Now I became nervous, she stopped talking went behind me and pulled my panties down, and started to lube my ass, and used toys and vibrators on me for a while teasing my hole, until she used a strap on and fucked me rough and hard for a while. I don't know how long it was but when she finished she untied me secured my hands and led me to the bathroom to clean up, we then returned to the bedroom where she secured me to the bed. the gag was removed and a new one was placed that had a cock on it and secured it, she then proceeded to ride this cock attached to my face until she came. At this point, I still didn't cum Sydney removed the cock gag mask and hoped on my cock riding me hard until I had the biggest orgasm of my life. She then untied me falling down next to me kissing me then looking in my eyes and telling me she loved me. I looked at her and didn't say anything, she said this was all part of the fun what she said tonight, this is our secret. I then asked her did I really sent vibes I was Bi early on and she laughed and said no, but she did take advantage when I was drunk to see how I would like my ass played with, and that sent out a signal. She also did plan for me to see her box to see if I would be into any of that, and I guess you were.

As we lay there she said I do love you, and you don't have to say it back, its when I said I am falling in love with you also why do you think I was honest that I was into this. We continued to talk while she rubbed me getting me hard, she then asked can she have one more thing before we fuck again. She said you know how much I love my pussy to be eaten, while I love for it to be eaten after I have been fucked and for my significant other to clean cum out of my pussy. I didn't need to be told twice and got between her legs and ate her out like it was my last meal driving her crazy while she pulled my face hard into her pussy while I cleaned every drop of my cum out of her. I then got up and fucked her while we kissed sho she can taste it but we didn't fuck we made love that night.

The rest of the weekend she role played ting me up playing with my ass and fucking it a lot, I fucked her a lot and each time I cleaned my cum out of her pussy driving her crazy each time.

Part 3 Where Sydney and I take this to the next level and fuck others.