The Sissy Journal
The Sissy Journal
by Lady Jayne Hills
Detroit Sissy Society CEO and True Boss Bitch
Day : 03/13/2019
Time : 1:30 PM
How : Gr****r
Where : His Place – House
Name : ? 001 ?
He hit me up on gr****r. We chatted and swapped pics. Sent girly pics first, then boy pics. He wanted to meet up right away.
I went over to his house in boy clothes. He lives only a few blocks away. I walk in…
As tall as me. Olive / white skin. Chubby Hairy Daddy Bear. Glasses. Cute.
We sit in the front room and I light a joint. We puff it once before clothes start coming off. I show him my freshly shaved legs and asked if I shaved all the way to my ass. Of course I do and he wanted to see. I strip completely and turn my ass in front of his face while he sits on the couch. He touches and spanks my ass. Then he stands up and takes his pants off. OH MY GOD, HE IS UNCUT!!! I have never sucked an uncut cock, so I quickly get on my knees to give it a try. LOVE IT!!! He likes deep head. He wanted to fuck me, and tried a few times, but I wasn’t “ready” ( I explained it to him after ) for anal. He stood over me and worked my mouth and throat till he was ready to cum. Asking where I wanted him to cum, I opened my mouth and stuck out my tongue. I let him cum in my mouth and kept in in for a little bit after. I spit it into a tissue that was in my jacket pocket. HOT ONE, HAVE TO DO IT AGAIN!
UPDATE – Saw him on gr****r as part of a couple. That explains his time restraints.
Day : 03/15/2019
Time : 10:45 PM
How : Texted old hookup
Where : His Place – House
Name : Xxx
I texted an old hookup that I haven’t talked to in 3 years. We used to hookup every couple of weeks. He has not ever seen me in sissy dress or had any idea I had sissy tendencies. He was excited to hear from me and we made plans to meet at his house later that night.
When I pulled up he was waiting on the porch. We hugged and smoked a joint, caught up on each others lives, then I went to the bedroom to get “ready” while he waited in the den. I quickly did my makeup (total fail, it is much harder than it looks and I need more practice) and put on my brown wig. I slipped into some black thigh high sheer stockings, a garter belt with clips, kaçak casino a black top-tie bra top, and my pink sissy clitty ring.
I got on my knees on the floor and called him in. He was impressed and took little time getting his cock into my mouth. We moved to the bed and it became clear to me why girls wear hair ties to bed. The wig kept getting in my eyes and mouth every time I put his cock in my mouth. So it was time to ditch the wig :(, but I had my mind on dick and was not going to be stopped.
He suck me, I sucked him, he rimmed me for a while (ooooo he is good at that), and I pulled out my but plug. It is black silicon with a pretty purple gem in the end. I lubed up and he sucked on my nipples while I slipped it into my pussyhole. Once secure, I crawled down to his cock and sucked him to his hardest point. During this thorough sucking, I used some more lube to pull the plug out. I straddled him and slowly lowered my sissy ass onto his hard cock.
Ok, he fucked the hell out of me. 4 different positions and lots of sissygasms for me :)!!! I finished him off in my mouth and swallowed. A+++
Day : 03/16/2019
Time : 7:40 PM
How : Gr****r (reg)
Where : His Place – Apt
Name : ? 002 ? “Xxxxxx”
Was horny and having no sissy luck finding dick. Set up a non sissy 🙁 gr****r. Found some dick.
Set up a meetup at his place. Came in and we sat at the kitchen table and smoked a joint. Found a common interest in books and history and he started to show me some historical pieces. With the historic book and artifact still in his hands, I started rubbing his cock, slid his pants down, and started sucking him.
We made our way to the bed and WOW, he is great with his tongue, really into nipple play (BIG +), and can deep throat without pinching my huge clitty. He was incredible. Lots of oral and asseating. No anal and we both came on his belly. Will have to do that again.
Day : 03/17/2019
Time : 2:00 PM
How : Going Out
Where : Bxxx Xxxe
Name : ? 003 ? “Daddy” ; ? 004 ? “the gentleman”
Feeling so adventurous. I have a grand plan that will test the limits of the secret part of my secret sissy habit. I did a really good job on my makeup (I watched some “how to” videos on youtube) and headed casino oyna out to the gay health club.
Once there, I put on my pink wig, pink glasses, gray and black bra, black panties (silky), black garter belt with clips, my favorite pink sissy clitty ring, and sheer black thigh high stockings while getting ready in the locker room. I was approached immediately by multiple men (all daddy types) before I even had my things put away.
I wrap a towel around me (like a lady does, over my titties of course) and started to strut around to see the happenings of the day. There were men in the sauna, in the hot tub, a man in the sex swing (just waiting…), and a few men in a room with a large L shaped bench facing a large screen playing a porn scene of the yummiest guy getting sucked off. This is where I sat for a minute.
I sat at the edge of the bench closet to the yummy porn screen. I notice 4 doors across the room with empty gloryhole booths. This place is amazing!!! There are two men sitting on towels, stroking on the bench. The one closest to me is cute. Mid to late 40’s, a little balding, in good shape, and a very nicely shaped cock. I had a girlfriend in h***school. This guy looked exactly like her dad. This was a massive turn on for me.
He took an interest in me and started stroking my stockings while he stroked his cock. I was really turned on, so I scooted in closer and he started rubbing my clitty thru my panties. I stood up and gave him a little spin around so he could see my little silky lacy ass. He grabbed it and squeezed it. He slipped his hand into my panties and rubbed my sissyhole.
I told him to stay put for a few and I would be right back. He said if I was coming back, he would wait patiently. I didn’t want to get cum in my wig before I had a chance to take some pics. I found a large mirror in one of the hallways. I dropped the towel and started to snap away. Once I was satisfied with some selfies, I went back to find Daddy.
He was right where I left him, stroking on the L shaped bench in the porn room. I sat next to him and he started pinching my nipples. This is my biggest weakness, so at that point, he could of had anything he wanted. After some nipple play I slid canlı casino siteleri down to suck him off. I knelt in front of him while he relaxed on the bench. I sucked him and sucked him. I wanted him to cum soooooo bad. I talked very dirty to him. I could tell he was nervous with all of the people around, and he couldn’t cum 🙁 . I had him whisper his number to me and I was on my way.
The rest of the trip was very eventful. There was an older sissy there who kept me company. I watched her suck off two different guys in 10 minutes while we smoked a cig. She had a blonde wig and fishnet stockings. She was soooo sweet.
I found a “dark room” that was kinda scary looking at first. I was looking in when a lovely gentleman started stroking my pantie covered sissy ass. I asked what was in there and he said it was just a dark room set up for some public type of privacy. I liked the sound of that so we went in. He started kissing my neck and nipples. I could not see a thing. I felt the wall next to me, and there was a gloryhole, 4 of them. This place is amazing!!! More men entered, no clue how many, when the gentleman started to suck my sissy clitty. I had not had a clitty sucking yet, so I was game. While the gentleman was sucking me, I spotted a large black daddy giving me the eye. I tried to motion him with my head to the other side of the goryhole. I would love to try a bbc Daddy, but he didn’t make the move. After a few minutes, I parted ways with the gentleman and went on my way.
I walked the halls, took some pics, watched some porn, and was approached and complimented more times than I can count. The group was soooo sweet and respectful. I was starting to get another idea, leave here and go to the gay bar to have a drink. I get ready to go but I leave my pink wig on. When I get to the car, I light the half joint in the cup holder and look up directions to XiXx’s. They are not open for a few hours 🙁 . Too bad, guess it is time to go home and write out this glorious tale.
UPDATE – “Daddy” texted me and we have a date in a few weeks 😉
This story was written by Lady Jayne Hills
Detroit Sissy Society CEO and True Boss Bitch
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