Ex-Girlfriend Kerry Becomes Fun Friends with Fetish Benefits – Part 1

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It started with an IM from an old girlfriend, Kerry. “I’m sorry to hear you and Susan are done, what happened?” My reply was guarded. And, it wasn’t really her business anyway, “You know it just didn’t work out. We had a pretty good run, but kids, finances, etc., just wore us out, I think”. After some back and forth exchanging of updates in our lives Kerry asked a pointed question: “Did you ever explore that kinky streak of yours with her?”.


As an ex-girlfriend Kerry had some deeper insights into me. But, in truth, my kinky streak was attributable mostly to her and her need to dominate. I mostly went along for the ride, unable to resist her. I also recalled enjoying being kinky with her. It had been a lot of fun.

But, I wrote back, “No, not really, my ex wasn’t as adventurous as you were or perhaps still are?”

Kerry didn’t answer and turned to discussing kids, both hers and mine, my living arrangements and life in general. Then, she said: “I have to sign-off, but I’m coming to Boston in a couple weeks, do you want to get together?”

“Yes” I replied, not believing my potential good fortune. “Just let me know when you’ll be here. I’ll even pick you up at the airport if you want”. She said: ‘I’ll let you know. Goodnignt”.

Good Fortune

We signed off and I went to bed. I couldn’t help but recollect our time together We had dated only for a short time – just 2 months. It had been a very sexually wild time for me. Kerry, even then was a bondage and domination affictionado. She had dominated and used me sexually almost continuously. Once even affectionately calling me “her walking hard-on” right before using the hell out of me for a weekend.

In truth it was easy to be that way for her. Kerry was a very beautiful girl. Red hair, dark green eyes, full firm breasts, long legs and milky white skin. She was tall, standing 5’7″ in bare feet. I wondered more if she still retained her looks after 20 years. In fact, in general I found myself thinking about Kerry, a lot. I wondered if she still had that domineering sex drive.

I had a hard time getting to sleep.

A few days went by and another IM popped up: “Hi there, I’m going to be in town next week-end. My flight lands at Logan at 7pm. Where are we going for dinner?” I told her I’d find us a restaurant and get a reservation. Out of the blue Kery then said: “You know I’m going to want to play after dinner”. After a moment I said: “No”, but that’ll be fun, though I haven’t “played” since we broke up.” Kerry then wrote: “Lets talk on the phone. I’m going to call you. I want to hear your voice”

My phone rang and I answered: “You do know I never gave up being a domme”.

Fantasy Lives on

Kerry and I hadn’t kept up with each other since we’d broken up years ago, though we were “friends” on Facebook. So, I knew she’d divorced and where she
lived and other “public” details of her life. Her public profile never had anything suggstive of kinkiness, so I didn’t really know about her continued dommeliness.


I just said: “Nope, but I didn’t think you would – as I remember you were spectacular in that leather body suit you had”. Kerry laughed and said: “I’m bringing it with me”. She added: “Do you have any of the toys I like to play with?” Again, I said: “Nope, should I get some?” Without hesitation she rattled off a list of items for me to acquire for the end of the week. She also said: “Dennis, no jerking off between now and Friday, OK? I want you fresh and horny, just like when we dated” “OK”, I said. “I gotta go” was Kerry’s reply. “Get those items please”.

After she hung up I thought about her in that leather body suit…..and definitely wanted to jerk-off, but didn’t. I had promised after all. The next day I went shopping for Kerry’s toys. It was a long list: Anal plugs, various restraints, a gag, various implements for inflicting pain, etc..

The next evening she called me again. We talked about the week end. She said after dinner Friday we’d play it by ear. I told her I’d completed her
shopping task. She was pleased, saying: “I’m really looking forward to seeing you. I wonder if you still have what it takes to keep up with me”.

Can You Still Keep Up?

I wondered that too. She said she’d call me Friday before getting on her plane.
It was a long couple of days. But, at last she called. “I’m in Chicago, about to board my plane. I want you to get the smallest butt plug in the package you bought, insert it and wear it on our date tonight as a reminder of old times”. I responded, should I call you “Mistress”, too”. After a moment she responded “we’ll see”. Then, “See you in a couple hours” and she hung up.

I waited awhile contemplating the evening ahead. Then I got the plug, inserted it and left for the airport. I hadn’t had anything up my ass in twenty years and it was a bit uncomfortable. But, by the time I got to the airport an hour later it was better. I waited for her at the curb of terminal C. I saw her exiting and I got out of the car to greet her. We hugged, she kissed me. As she did she reached around behind me and discreetly pressed on my ass crack to see if I’d complied with her wish. She also felt my erection poking her belly. She laughed: “its so good to see and feel you Dennis. Its going to be a fun evening”. “Be a dear and put my bag in the back and lets get some dinner”.

Dinner Time

The restaurant was dark and intimate and served very good italian food. We mostly chatted about our lives over the years since we broke up. We had gone in separate directions, she out west for a career and marriage then divorce. Kids mostly grown and in boarding school or college. For my part it was a similar story. Eventually, Kerry decided we should go. I paid the check and tipped the waitress. On the way out Kerry held my arm and in lowered voice asked: “Do you remember the significance of an inserted butt plug?” I didn’t, but her saying it made me remember. When we had been together, the rule was: as long as I had the plug in I was to be her slave and obey her commands.


I said: “I’m supposed to obey you as long as I have it in”.

She laughed: “That’s right. But its more than that. You are my slave as long as its in.” “Now slave, take me to your home. I want to play.”

Home to Play

We got to my house – in a quiet neighborhood north of Boston. I retrieved Kerry’s luggage and escorted her to my home. Upon entering, I showed her
around the house and brought her to a guest bedroom. She said: “Slave. I’m using the master bedroom and you will be entertaining me there.”


Once in my bedroom, she had me strip for her. She then commanded me to assume various slave positions. I struggled to remember what was what. She often laughed at my ineptitude. And, then said: “At least you still try hard to comply”. With that she had me undress her then she laid back on the bed with her legs spread and pussy beckoning to me. “Now let’s see if you still remember how to please your mistress with your tongue.”

Two hours and several orgasms later, Kerry told me to stop. Callig me Dennis she said “you have not lost one skill, at least”. I stood and stretched, thanked her for her kind words. After no sex for over a week I was afflicted with an enormous raging hard-on. Of course Kerry saw might plight when I stood up. She sat up on the bed and had me stand in front of her with legs spread and hands behind my back. She began to fondle me, probing, squeezing and pulling on my member. She observed my reactions and got the impression that she was learning a lot about me. Of course, with all the prodding, pulling and stroking she was doing. I was producing lots of precum. She’d occasionally lick my juices from her fingers and sometimes would have me lick her fingers. After a while she said: “You really need to cum don’t you”. I just mumbled somewhat incoherently a “yes maam”. Kerry said: “OK, I need a good fucking after all that oral attention, do you think you can fuck me to orgasm without cumming until I tell you too?” I only grunted a “Yes” and she pulled me to her.

Yes Ma’am

We made love for a long time. It was a terrible struggle for me to not cum. When I felt her body shudder with orgasm she said “cum inside me now
slave”. I fucked her like a mad man and came hard inside her. Afterwards, I collapsed on top of her and we cuddled exhausted from our efforts.

Kerry told me to go to the bathroom and remove the plug in my ass. I did and after cleaning up came back to her in bed. I told her she was still the most spectacular woman I’d ever been with. She just smiled and kissed me, saying: “You were great, but let’s talk in the morning”. She snuggled into me and went to sleep.

Morning came early that Saturday. I awoke to Kerry stroking my hard cock. She smiled saying: “I really like a hard cock in the morning.” She then mounted me and began to fuck herself on my pole. She said: “No cumming until I say OK?” Again, I agreed. She used me hard for an hour and a couple of orgasms. She didn’t let me cum.

Dismounting me she said: “Ever since I saw you had divorced I’ve wanted to make you mine again. But, now I want more. Before, I just wanted you as a human sex toy. Now, I want all of you. As in a full Female led relationship”

Full Time Female Led Realtionship

Laying next to Kerry with yet another raging hard-on it was all I could do to resist saying “anything, just please let me cum”. But, I didn’t. Saying instead: “Kerry, I love giving myself to you. And, think you are fantastic, but, I’ll need to think about it”. She said, “there’s no rush” “maybe I can do more to convince you”. She began stroking me and looked into my eyes and saying how she always knew my needs and desires. “Just relax Dennis I’m going to show you how much pleasure you can experience with a domme you can trust and love”.

She stroked and licked and sucked for what seemed like hours bringing me to the edge of climax time after time. Finally, she said “give it up for me Dennis” Squeezing harder and jerking my engorged cock I began to cum. She grabbed my ball sac and squeezed gently while jerking me. The effect was an incredible, powerful orgasm with cum flying up in the air. splattering on me, her and all over the bed. Kerry stroked me long after climax to the point of it being painful, getting everything I had to give at that moment. She stopped and said let’s shower and get some breakfast.

We cleaned up and I found the energy to cook a basic breakfast for us. After we ate, Kerry took my bathrobe off and said: “I like you naked. But, I’m going to dress while you clean up”. I finished the dishes and headed to the bedroom.

I found Kerry wearing her leather body suit. Hair in a pony tail. She said, “insert this and be my slave” handing me a larger anal plug than from the night before. I took it, found some lube and inserted it. Kerry said: “You may now address me as Mistress or Maam, slave”. “Now lets talk some more. You may only speak when asked. Understand?” I said: “Yes Mistress”. “Good” she replied. “earlier today you said you weren’t sure about an FLR with me”. Even though I think you love or want to love me”. “So, here is what I propose”. “I’m still living out west but I have a job offer here that I’m going to take”. “Its going to take a few months for me to wind up my affairs and come east full time”. “I’d like you to be my slave toy at least while I try to convince you that you
should fully give yourself to me”.

After a pause shed said: “You may speak now slave”.

I said: “Mistress, if I understand, you propose that I be your slave toy when you are here and that we work towards a deeper FLR as we go. Is that correct?” “Yes” she replied. “I accept” I said.


Kerry came to me and kissed me. This immediately produced another erection on my part. Noticing my erection Kerry smiled and said: “You are a horny slave”.
“Now that we have that settled we’ll need to take care of a few things and start your training”. She’d said: “get the items you purchased and bring them to me”.

The items were in the bedroom closet so in minute were laid out on the bed. Kerry chose a pair of wrist cuffs, put them on my wrists and attached them
behind my back. She then went into her bag and pulled out a black leather collar with a tag on it that said “Dennis” on one side and “Slave” on
the other. She placed the collar around my neck and secured it with a lock. Next came a leash, which she attached to the collar.

Collared & Leashed

Pulling me by leash she brought me to the bathroom and had me stand with my legs spread wide apart. “I’m going to shave your pubs. I like my naked slave’s
cock and balls to be smooth at all times.” She then proceeded to carefully shave the hair from my genitals, scrotum and around my anus. She used
a bunch of lotion afterwards. Bringing me back to the bedroom by the leash she reached into her bag and brought out a cock harness with attached ball stretcher and put it on me. This of course made my hard-on even harder. Kerry said: “This is going to make your cock bigger and more useful to me. You’ll be wearing it a lot, even when I’m not here”. Next came a body harness that I had purchased, ankle cuffs and finally an even larger butt plug. “You realize I’m going to want to take your ass before I go tomorrow”. “Yes Mistress” I said.

Now “dressed” and restrained, Kerry grabbed a flogger and began giving me commands. “Kneel, present, punishment, tongue, open” I had to quickly get
into the positions required and hold them. If I was slow or wrongly positioned myself she would strike me on the ass with the flogger. After several hours
of this training, she told me to stand and present, meaning I had to plant my feet eighteen inches apart at 45 degree angles with my cock thrust forward. She stroked my ring encased cock making it harder and larger. “Would you like a break from training slave?” “Yes Mistress, I said” “So be it, you will kneel by the bed and pleasure me.” She removed her leather pants and lay back on the bed pulling me gently towards her. I dove into her and strove to please her with several orgasms. Which she had.


After recovering. Kerry had me stand and removed my restraints, except for the cock harness and collar, saying: “you will need to earn your next release slave”.

It was late afternoon. Kerry said she was hungry and that I should go prepare a meal for her. I turned and went to the kitchen making a simple pasta salad. “I apologize Mistress for my lack of cooking skills”.

Kerry thanked me for the meal and had me stand behind her while she ate. After eating, she said I could serve myself then cleen up and join her in the living room.

After dinner I went to the living room. Kerry instructed me to kneel by her side with legs spread wide and hands on my knees. I held that position for a long time. But after a while my legs began to shake. Seeing this Kerry had me stand in front of her. Feeling my legs she said your legs are strong. But, like the rest of you untrained. She massaged the muscles in my thighs and also took the opportunity to play with my cock and balls making me hard and less comfortable in the cock and ball harness I was wearing.

Kerry said: “go to the bedroom and wait for me there”. I did and a few minutes later she joined me. “Assume the punishment position” I knelt head to floor, ass lifted up as she had taught me. “your punishment will be a taking of your hole, prepare yourself”. Kerry got a dildo from her bag, strapped it on and knelt behind me. I had removed my butt plug and was waiting with trepidation when I felt the head slowly entering me from behind. She then began to slowly fuck me and then faster and faster.

Kerry began to come from fucking me. My cock was raging hard and leaking precum. All of a sudden she stopped pulled out and told me to rise, clean up and come to bed.

“May I speak Mistress?” I said after joining Kerry in bed. She said: “Yes”. “Why was I punished, Mistress?” “Because, regular punishment is part of your training”. “You will be punished weekly from now on, even if you have been a perfect slave. This will acclimate you to the reality of status as slave. Punishments will be light and possibly enjoyable for you if you perform well, more severe if you do not. The level of severity will be my decision”. “Do you understand slave?” I said simply: “Yes Mistress”.

“Roll over on your belly” Kerry instructed. I did and she cuffed my hands behind my back. Then instructed me to roll over on my back again. She
then removed the harness from my cock and balls, took out some lube and began to work my now sore and swollen genitals. Inspecting my cock and balls she said I was holding up well to her treatment of me. And started stroking me more vigorously. “Don’t cum unless I give permission” she said. Then she swung her pussy up over my mouth and said “eat”. While I “ate” her she worked my cock to one edge after another. She came again, then again. After over an hour she rolled off me satisfied and lay next to me gently playing with my cock. After a while she fell asleep, then so did I.

Sunday Morning


Sunday morning again came early. Kerry awoke and released me from my bonds. She told me I’d been a good slave this week end. But that today we were just going to be a regular couple. “You know Dennis, I always treat my boyfriend right”. She kissed me, I responded and We made love for rest of the morning, then showered together and went out for brunch. The Mistress / Slave dynamic gone for the moment and replaced by just Dennis and Kerry.

We had a great day, walking Boston learning more about each other and generally enjoying life. Later on that day on the way to the airport Kerry asked me what I thought of our weekend together.

I said: “Even better than I remember. What about you?
She replied: “I’m still tingling all over” I can’t wait to get back here and have you again. “But, if our new relationship is going to work I’m going to have to train you.” “It may not always be pleasant either” she continued. “But, I will IM you when I get back to my place and we can begin your training”.

We got to the airport and Kerry kissed me passionately saying “good bye for now, Dennis” “Good bye Kerry” was all that I could say. My thoughts were already jumping ahead to the “training” I was to receive. Kerry leaned back into the car and said: “remember, no orgasms without my permission”. “Yes Mistress” I said. She smiled and walked away…

Find your Mistress


The Reluctant Mistress and Her Unexpected Transition – Part 13

The Reluctant Mistress and Her Unexpected Transition Part 9


2 thoughts on “Ex-Girlfriend Kerry Becomes Fun Friends with Fetish Benefits – Part 1”

  1. I’d love to find a Mistress like that to serve and be her slave. Better yet if she was a trans sexual Mistress. That would be my dream come true!!!

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