Author: Sissyjennycuckold

[M/F…M] Late Night Blue Lights [nc] [humil] [Mdom]

*I’ve written a few stories that range in topic and points of view. Typically I write first person, but this is an early attempt at third person. Please let me know what you think and I’ll take any constructive criticism you can provide.*

​

It was late, nearing midnight as James drove Anna home from the bachelorette party. Anna’s old college roommate was getting married the following week. The hour long drive back to their house was mostly on rural back roads. Two lane highways where the speed limit is often lowered with little notice. 

James and Anna had been married for over eight years. Their nights were typically not exciting and Anna used this opportunity to let loose. Anna was quite intoxicated when James arrived to pick her up. Anna had spilled a drink on herself at some point in the night the odor was still ever present as she rode home. 

It had been years since Anna and James had been frisky in the car and Anna felt like that should change. In her drunken state of mind, the long dark road with few passing cars would make the perfect time to perform a private blowjob on James. Initially James thought she was joking, but quickly realized Anna was committed to the endeavor as she took off her seatbelt and leaned over the center console of the minivan.  Read more »

[MF][cuck][sissy] Solder gets fucked in more than one way [Part II]

A few hours later I get a phone call, it’s Amy. She needs me to bring the car back so she can drive Kyle back to his car. He couldn’t park it at our house. I refuse at first but give in. The motel room might be driving me crazy. I need to try to put things back together with Amy. After Amy leaves with Sarge, I go in the bedroom. The bed is a mess, it smells of sex and on closer look, I can see dried stain outlines on the sheets. My curiosity and I guess I was glutton for punishment, I check the dirty clothes hamper. I pull out 2 new pieces of lingerie I’ve never seen before. I start picturing Amy wearing them and what they were doing in bed. I can’t stop myself, I unbutton my pants and start masturbating again. It’s uncomfortable and somewhat painful but I start rubbing her dirty lingerie on my cock. It’s soft and feels cool to the touch. I put the other piece of lingerie up to my nose and breath in her musty aroma. My body spasms as I orgasm. It hurts and I double over, pulling everything away from my little sensitive red cock. Thinking to myself, maybe 4 times in 24 hours is over doing it a bit. I’m not 15 any more.  Read more »

[MF][cuck][sissy] Solder gets fucked in more than one way [Part I]

My wife Amy and I met each other in High School. We started dating our junior year and only had a few break-up fights that never lasted long. I think the longest time we spent broken up was 3 months. We were pretty frisky since there wasn’t much else to do in our towns. We tried to practice safe sex but, sometime we just didn’t have condoms on us all the time.

Sure enough, halfway through our senior year, she gets pregnant. I think we found out in early February, I remember telling our parents just before Valentine’s Day. It went pretty much as expected. Our Moms flipped out and Dads just asked what am I going to do about it. I told them I was a man and would take care of her. Amy and I hadn’t really talked about it yet but, I told our parents I was planning on marring Amy and providing for our family.  Read more »

[MF][cuck][sissy] Solder gets fucked in more than one way [Part III]

The time came as the video ended. Sarge softly whispers in my ear, asking if I was ready. I wasn’t but I wanted to be. I wanted to be his slut. I wanted him to fuck me like he fucked my wife. Sarge pulled out a large bottle of lube and started slathering it on his cock. He told me to kneel, leaning over and to bite the pillow. This scared me. My body turned cold as I got myself into position. I felt his hand pull the crotch across my ass and put his finger covered in cool lube against my asshole. He swirled it in a circle before applying pressure and it quickly slide in. “Have you ever done this before?” he asks with a rough voice. “No, have you?” I meekly respond. I can feel his finger slide deeper in. I wait for his answer as I feel a second finger trying to make it’s way into my ass. I clench up and he backs off a little before pulling his finger in and out gradually fast. He then slides the second finger in quickly and with a bit of force. I gasped and bit the pillow until the pain subsided. After a few minutes I feel him shift around and pull his fingers out. He placed his warm cock head at the entrance of my ass and said, “I’ve done this before but never twice with the same girl”. He let that process in my head for a full second before plunging half his cock in me.  Read more »

The Secret International Society of Sissified Youth (SISSY) Order [Trans][Submissive][Sissification]

I am a card-carrying member of the Secret International Society of Sissified Youth (SISSY) Order. Well it’s not really a card but, more of a ring. This is my story of how I became member. I’ve been with the Order for 10 years of service, 8 of which were great. I’m not sure if I’ll make it to retirement but this is my story of how it all began.

It all started really when I was 11 and began dressing in my Mother’s clothes. I didn’t know what it was at the time but, being in women’s clothes just felt right. That might have been due to be molested by a neighbor during that time period but, I don’t look at that in a negative light. I believe he was just helping me find the way to my true self. Who knows, maybe I was asking for it, god knows I would do it all over again the same way if given the chance. Read more »

[CD] to [cuck] Wife tells the story of how it started

My husband Ron and I have been going through some rougher than normal patches for the last few months or year. We have been married for 15 years and together for 17 years. We met early in life, actually while still in high school. Yes, we were high school sweet hearts but, neither of us were completely “unexperienced”. While I believe my past was a little wilder than his, he was handsome, sweet and made me want to be a good woman for him. Ron, was always a quite person and didn’t talk much about his past. That was good for me because I didn’t really want to talk about mine either. So, through the years we grow together. Yes, there were some fights but, nothing major.
One night a couple years back, Ron and I are talking like the best friends we are, while we are drifting off to sleep. He tells me that he used to dress in women’s clothing. This didn’t completely shock me, I’m aware a lot of boys crossdress at some point growing up. I console him, telling him that is no surprise and we fall asleep soon after. Read more »

[inc][Fm] Camgirl Mom get in too deep and money-hungry(long)

I’ve been a devoted viewer to Crystal web-cam show for a few months or, others know her by the screenname TrailerQueen86. I found Crystal just a few days after she started. She was eager to get and keep viewers. She would do things on the free cam that others wouldn’t, things like play the insertion game. TrailerQueen86 would pick a random viewer and they got the opportunity to select any item in her trailer for her to insert into her vagina. I have to hand it to some of these sick guys. They would pick out some random stuff. I once saw her the majority of a PlayStation 4 controller in her. She even tried to play a game while masturbating with it.

This is where some of these guys found out she has a 15-year-old son. Crystal tried to steer the conversations away from her personal life but; as the masses found more exciting cam-girls to watch, she was left with a hand full of dedicated viewers. I’d say about 6 of us watched her regularly. We had become familiar with each other and the taste of what each other enjoyed. We all contributed a monthly donation to keep Crystal behind the camera. She was constantly worried about money, we all felt bad for her. She didn’t an easy life. Crystal worked at a local restaurant as a waitress and was raising her 15-year-old son alone after his father left a few years ago. Read more »

Abducted and Used [cd][Mm]

I was a strong minded fifteen-year-old boy. This was in a time before cell phones or fancy internet could provide outlet or rescue for me. I was fed up with my Mother’s ridicule about catching me crossdressing again. I had enough, I picked some clothes in a duffel bag and simply walked out the house. I remember her nagging and threating me. She was daring me to leave. Leave just like my Father did when I was younger, she said. That’s what I did, I walked right out and down the street while she kept yelling from the porch.

I started walking, I didn’t have a plan or a real direction to head in. I lived in a small town in a very rural area of the south. It’s the sort of town that doesn’t even lock the doors to the house at night. It was a 10 to 15-minute drive to the next town and I had no idea how long it would take me to walk. I didn’t care, I needed to get out of that house with that woman. There were only 4 roads that led out-of-town. I knew I needed to pick the least likely she should look for me on. I feared she would call any friends and family in the area to try to find me and possibly have them look for me. Read more »

Crossdressing Teen with Step-Dad part II

This is a continuation of my previous story – link in comments.

A few months have passed since my first night with Chuck. Our relationship has noticeably improved, as my Mother has even made a comment or two. I’ve started my senior year in high school. Thanksgiving is soon around the corner. Chuck has become accustom to receiving blowjobs from me regularly. At least twice a week, he visits my room with a light knock on the door. One particular night was different though. He knocked and entered, presenting me with a gift. He set it on the bed and said he’d like to see it on me, he said he’d be back in a few minutes. Read more »

Crossdressing Teen with Step-Dad

I was an only child to a single mother for all of my life. Well, that was the case until my Mom started dating Chuck. I was fifteen when fourteen when Mom met Chuck and married him a year later. I wasn’t the typical “young man” and didn’t try to challenge Chuck, who was proud to assert his Alpha male status when Mother wasn’t paying attention. You could say Chuck and I never really got along, although I was glad he made my Mother happy.
Everything changed during the summer of my Junior year in high school. Chuck worked as a handy-man/contractor and owned his own house renovation business. That summer, everything to include myself thought it would be good idea for me to work with Chuck. This would give me some “bonding” time with a father figure and maybe learn some helpful skills for later in life. Not to mention the fact it would give me spending money. I’ve seen the worst of Chuck’s behavior, I’ve dealt with him for a couple years for free, at least this time I would be getting paid.
As anyone in the contactor business know, work isn’t always steady, as I soon found out. Chuck would tell me to take the day off because he couldn’t afford to pay me for the piddle job he had lined up for the day. With Mom at work and Chuck out the house, this gave me the perfect time to play dress up. I’d been crossdressing since I was eleven. For me it was fun and a great way to pass the time while doing some choirs. Read more »