Becoming Sherry's Bitchboy

After being recently divorced the depression was showing on my face at work. I had no money after the financial hardship and working paycheck to paycheck. She worked in the same company and known her for five years she asked how I was doing knowing my predicament as word got around from work gossip. I made small talk a few times and she asked me out which I immediately refused as I was broke barely paying my bills. A week or 2 later same thing she asked me out to a concert and I respectfully declined. Another week or two she asked again about restaurants and I told her some good ones in the area and she said "Lets go my treat and you can buy next timem" knowing my tax return was coming and could use a good time I agreed. Little did I know how much my life would change. She was about 5' 3" a solid 130 from playing sports like girl's softball and weights at the gym with short brown hair and plain Jane face.

When word got around we were going to go on a date an older lady at work said she thought she was a lesbian which kind of shocked me as next time I saw her could see the tendencies. Went to a steak place had a good time and since she liked sports said lets watch some football this weekend and she'll bring the food and I supply the beer and said ok. We enjoyed and became friends and since I was on the way from work to her house would pop over my house to check how I was knowing I was still in a fragile state as I would get emotional about the whole breakup. I never made a move on her and was watching mostly porn to get off and one day when I had forgotten to lock the side door with my headphones on she walked in on me jerking off to porn actually Femdom porn and was in the room for quite a while I was to learn later. To my shock she was there as she never saw me naked before and here I was all 5' 9" 220 with my 6" cock all lubed and hard.

Being so embarrassed I quickly covered up and apologized as she said none was necessary since she intruded on my privacy and as I dressed in another room she quickly checked out the sites open and did a fast glance at my history of site visited. They were men feminized by Dommes as well as many strap on videos. When I came back out still red in the face she said she had to leave and see me around. I was mortified when I discovered she had seen my deepest secret. Seeing her at work I tried to avoid but ran into her in a corridor, no mention but said lets get together for a beer and she popped by that afternoon and once loosened up by the beers she brought up what happened the other day and I admitted those sites and scenario turned me on. She got quiet and silent and finally said would I want to do that with her she wouldn't mind if it made me happy, what a friend lol. I told her some porn sites so she could do some research and said this weekend is good.

On Saturday she came over after small talk told me to strip as my body after years of sports and manual labor was decent but inactivity had made me soft and a beer belly and I could tell she enjoyed looking it at as I started to get hard. From her sports bag she pulled out a belt and told me to get on all fours and then started fondling my balls and jacking me from behind until I felt her belt whipping my ass and telling me I deserved it for being sneaky and a secret masturbator. She beat my ass for a solid 15 minutes until I was a started to tear up and my ass covered in stripes as she said I was going to get this every time she was over if I didn't obey her. As I started to cry real tears she saw and then really gave it to me across my thighs until I was crying like a little boy wailing and my whole body and ass shaking until she stopped. She had broken me and told me its as yes ma'am no ma'am from now on and follow her orders.

As I got up from the bed she said to give her a hug and as I did I started crying again as she held me if anyone was watching would see a naked larger man hugging a small fully dressed women bawling his eyes out. after letting me go and seeing I was hard she told me to prop myself up on some pillow and jerkoff for her as she wanted to video on her phone I was a little scared but complied as she captured my masturbation technique on her cell and I shot off 3 ropes of cum in the air. After cumming the feeling of being a normal guy returned as I showered an she was waiting when I got out and went to my bureau to get some clothes and she said no she wanted me to stay naked for the rest of the day I said I was going to get dressed and ignored her she walked up to me and punched me hard in the stomach all her strength as I folded over she punched me twice in the face as I backed away into a corner for a chance to recover she got me against the wall and a series of punches to my arms stomach and thighs as I sank to the floor and as she grabbed me by my neck cocked her arm back and said "I will keep punching your face and give you black eyes and a cut lip if you if resist me."

As she stood over me with her fist ready my will crumbled and I started to weep with real tears as she watched, her break a man and make him succumb to her will. I got up and went to the kitchen for a drink with her behind me and stayed silent. She told me its for my own good and she would beat me up again if I tried to fight it. I was quiet and she told me she wanted a key to my place and my password as she was going to incorporate changes to my life and had the video she would share at work. Well my choice was either to kill her or obey and I chose the latter. She said she would check my net history to see what I was surfing and not to jerk off unless in her presence and I complied. I was confused by it all but in my state of mind not strong enough to think of a way out of this situation.

At work I was the macho maintenance guy in uniform but no one knew I was her sub now as we didn't let on at work he made twice the money I did and was doing her homework online of the femdom nuisances of controlling and owning a man in mind and body in addition to her working out at the gym I learned on self defense classes and increasing her endurance as she was rock solid and very dedicated in any thing she put her mind to. Very smart and disciplined woman a far cry from my existence. Her plan was unusual from other Dommes as she was going to break me physically and then mold me into what she desired I found out after the fact. Having access to my house she installed some apparatus on the garage ceiling beams for attaching me in place to accomplish that.

I knew after work to shower and stay naked if she came over which was 3 times a week during work days and full days on the weekend as she always wore name brand sports attire. I was whipped by her belt a couple times a week and she started to finger my ass being smaller 3-4 fingers were easily able to be inserted and knew she would soon fist my hole. It got to the point where I would get hard whenever she walked in and would touch and lightly stroke myself until she stopped me and would have to follow her instructions on what she wanted to do. intense ass beatings a couple times a week for training and one day took me out to the garage to secure me to a 4 inch caste iron pipe by the wrists as she went inside to get her bag.

She came back with her bag and put on leather gloves used for hitting a heavy bag and smiled as she told me she worked out for hours on one at the gym but i was her heavy bag now and proceeded to punch my gut, ribs, thighs, shoulders and face for and hour or so as her hands were small but so piercing with all her strength from her rock hard legs. The punishment was brutal and I winced and groaned eventually crying real tears which was her desired effect and really let me have it opened a floodgate of real tears flowing. She took a break to drink some sports drink and sprayed water on me leaving me in place telling me to get used to this. she took her phone out to take pics of me in position and the tears flowing on my face. She was always taking pics of me naked as well in many embarrassing shots.

Once released I was very angry and tried to regain my manhood and punched her in the face she was a little surprised and came at me I went to punch her again but she got inside of my arms and started going to work on my body hitting me in the stomach over and over with body shots until my arms came down as I tried to push her away my strength ebbing away as she was getting stronger hitting me at will as i begged her to stop. She was angry at my defiance and was going to teach me a lesson once and for all as she pounded me without mercy backing me up against the wall as I cowered before her sinking to my knees crying again until she stopped and said "Do you want more?"

I said please no more Sherry. I realized then she was my master and superior and not to challenge her. She told me to get in the house pushing me from behind and into the shower telling "Don't you ever try that shit again cause I will fuck you up like never before," and I believed her. I took a shower and she put me to bed as it was getting late on a work night.

I woke up the next morning for work very sore all over and shaving in the mirror saw the many bruises and black and blues all over from the neck down. My uniform covered them up and went to work with the guys talking their usual macho crap about sports, cars and women I was still in a daze how she has come to put me in real fear and under her control. I was working on a ladder in a corridor and she came from behind and started speaking and I jumped in fear of her voice like habit and she noticed and told me she'd see me after work. I knew to be naked at her arrival but wasn't getting hard anymore as i was in fear of what was coming next. Once she walking in opened her bag and told me to put Nair on from the waist down as she wanted me smooth. She said "I always knew I could take you and beat you up and that you were really a punk and I was right," after my defeat physically she was going to feminize me and upon my hair removal brought out pink. orange, red, purple thongs from now on I was to wear under my clothes and took all my male underwear into her bag for good. She also had a butt plug she lubed and I put the pink ones on as instructed as we watched TV.

Next morning for work I wore the red thongs carefully tucking in my uniform shirt so the guys wouldn't see when I bent over or used the men's room and the feel on them on the underside of my balls and asshole was distracting all day. Sherry came by and took me into a hallway closet to show her I wore them as instructed. She said she wasn't coming by until Saturday but to behave or else and I understood I told her. I got a text Saturday morning to wear my plug and nothing else when she arrived. She showed up with her ever present sports bag and took me into the bedroom and had thigh high black stockings she told me to put on and as I did she took a strap on harness and 10 inch dildo and attached it over her sports shorts and told me to get on all fours.

Being an anal virgin I pleaded with her to be gentle as she lubed her cock and placed it at my opening and just put the head in as I gasped and she grabbed my balls and pulled me onto her cock slowly until I was impaled all the way onto her balls. She let me get accustomed to its size and slowly started fucking with ever increasing speed until she was going full speed as I was screaming from the ecstasy of her cock against my prostate as she was pounding away her usual endurance on display she was giving it to me good and hard and I was her bitch. after an hour I was a wreck and she stopped as I crumpled on the bed spent as she went to the fridge to crack open a beer and proud of her achievement. She told me I was her bitchboy and get used to it as whenever she wanted to get laid I need to be prepared with no back talk or she'd beat the hell outta me worse than before and I believed her. One day we went to a sports bar and she had beer and wings I was only allowed ginger ale and some free salsa chips on the table and after when we were headed to the care she told me to get in the back seat and she opened her trunk and took out her sports bag and got in the back with me told me to take my pants off as she put her harness on and put me on all fours and started fucking me in the parking lot for a half hour.

Once finished she got me back home and made me strip and on all fours brought out a can of Crisco and greased her hand up as she said I was ready for her fist and she slowly and a little painfully worked it in up to the wrist leaving it in as I wailed about in pain and pleasure and totally in her control as a assboy for her as she took pics again. Granted I never kissed her, saw her naked or had any sex with her as I found out she was indeed a lesbian and enjoyed emasculating men in fact had a twin brother who I met once a whiny guy that she told me she had regularly beat him up from about 7 years old to his teens behind her parents back when he misbehaved, so this wasn't something new she had a dominant streak in her and I was her victim. After I was instructed after work to be be in stocking and garters she bought for me as I was always smooth from the waist down and even found heels to wear. I was a sight but my legs were pretty nice I have to admit.

One day expecting her arrival she walked in with me in femme attire and behind her was a young tall very Black guy I was startled and embarrassed but she acted like it was normal and introduced me to Jamal from her gym and to get him a beer and sit on the couch next to him. I sat next to him made small talk as she watched and his hand was rubbing my stocking thigh and Sherry said undo his pants and suck his cock, I was not surprised but never was gay but did as told and he was hard and very long about 9 inches and did what I was told and gave him a long deep blowjob and reworded with his cum which she told me to swallow. After he left feelings of guilt was how I felt but she said he's going to be a regular visitor from now on and he was.

Jamal got my phone number from her and would text me to come over I was in lingerie and he would strip with that black snake always hard and I'd drop to my knees and after he was really rock hard would bend over taking his cock good and deep and truthfully the best sex I ever had and now gay as I desired cock more. She had accomplished her goal and transformed me into a CD faggot for good. I saw less of her as she got into a deep relationship with a woman but we still chat on the phone as I have been serving Jamal for a few years now so it was all worth it.