Sissy Fag Locked In Chastity

Alpha Ape Meets Lady In Red

It was a Saturday afternoon and I was back home from university for the summer. I was walking through the mall looking for places to buy sneakers when I saw a gathering of women next to a stall. The women were hovering around it, so I walked over to the stall to see what was going on. As I approached the women parted and there was an old lady sitting there selling charms, which was unusual for this mall, they never had this type of thing here before, maybe a lot had changed while I was away at university. One woman stood out in the crowd, dressed in a long flowing summer dress and it caught my eye because her blonde hair flowed into the red of the dress and she had heels on that looked quite sexy. I could not hear what they were saying but I could hear a dainty voice which was sweet sounding so I waited until this lady turned around. When she turned around, I realised it was not a lady at all, it was a young lad my age dressed up as a girl, and a really slim long-legged girl at that. She had bright red lipstick on and alluring makeup, she looked really feminine. I was quite taken by her look, and I was especially comfortable with trans girls or sissy’s because I had Sissy Sarah at university, and our relationship was in full swing. So, I spoke out and said, “hey I love your outfit, you look beautiful” she turned and flashed me a smile before walking away, so I walked after her and said, “sorry have I offended you” and she said that it was ok, she was just having one of those days and was in quite a hurry. So, I asked her for her number and asked if we could perhaps meet up for a drink later that evening. I was in town for a few more weeks before returning to university so perhaps I could have a little fun while I was here. She agreed and said her name was cherry and did I know what I was getting into with a, you know what? And I laughed and said I was totally cool, so we planned to meet for a drink that evening.

Sissy Girls And Chastity Cages

The evening arrived and I got to the bar we agreed on early so that I could scope the place out and also see if there was any other talent about. I stood at the bar and took a look around…. the bar was heaving with bodies, and lots of sexy women. As I glanced towards the restrooms, I saw my lady in red had also arrived. Cherry was wearing a long flowing white summer dress with red petals on it. The dress was tight fitted to her figure and she had strappy heels on with red painted toes. She looked killer and the way she walked gave her a timid unsure vibe which really got me hard. She sat down and we talked and drank wine. I asked her when she had decided to be a girl and she said she had known all her life and just started to express it now as soon as she left uni, which aged her for me, and I knew she was maybe 1 or 2 years older than me… an older sissy girl... mmm.

I then asked her why she looked so shy and she said that she was just like that from years of bullying and also because she was now trying a new method of getting into her role as a woman…which was causing her some adjustment pain, which made me curious. I told her she was sexy and wanted to know what her new method was and why it was causing her discomfort to the point that she was walking a little funnier. She smiled and said “I am wearing a cage babe...”  I was surprised but I knew a little about cages, and I knew that chastity could be hot, it was something me and Sissy Sarah had discussed. I was excited and asked if I could see it, and I know how wild that sounds, but I was so comfortable being sexual with ladies and sissies by now that I felt no shame in asking… and lucky for me, Cherry smiled sweetly and said that I could if I was a good boy which just made my cock rock hard.

Sissy Girl Encounter

The drinks continued and the laughs got louder, we were both enjoying each other’s company and the night was going in the right direction. I was getting harder and harder and then Cherry got up and said she was going to the rest room, and headed straight to the disabled toilets. I watched her go, as a sissy I guessed that the disabled toilets were better for her, so that was no surprise. Then a horny thought flashed through my mind and I got up and followed her, she was just ahead and opened the door to step in, but I grabbed the door and gently nudged her in from behind to which she looked over her shoulder and gave a little giggle, I think she was expecting this.

Inside I pushed her up against the sink and grabbed her waist… pulled her in close and started kissing her, she kissed so sweetly that my cock felt like it was leaking already, I was getting wet tip just from being so hard for so long. We kissed and I ran my hands down her body… she leaned back putting her tight ass onto the sink, and then started to pull her dress up. As her dress went up, I got a look at her immaculately shaved perfectly shapely long legs which I got down and began to kiss. I kissed and licked her thighs until she pulled the dress up and over her crotch. Her tiny little boi cock was caged up in the tiniest of nub sized cages and was clearly wet and leaking, she had been so excited this whole time and this little lady had been leaking, she had come to the restroom to wipe off the cum. I was going insane looking at her, and I grabbed her cage, to which she gasped with excitement, and I moved it side to side to get a good look at her tiny cock, and tiny little balls hanging separately behind... all shaved and looking beautiful. As I moved her cage around, I could see her twitching and straining inside it... her lust was peeking and from the way she thrust her boy pussy towards me I had the feeling she wanted me to lick her cage, which was not something I had done, I was always very Alpha, but as she thrust her hips forward all I could see was her perfectly shaven taint and so I slid up kissing her belly and chest and neck and then grabbed her neck and with my other hand pulled her dress up and tucked it behind her neck. I then grabbed her tight tiny waist from behind and while pulling her hips out I pushed her head against the wall. I got down between her legs and spat on her boy cunt from behind, and she screamed a little. Looking at her hole I could see she was a messy little dirty girl, with a dirty ass, which contrasted with her perfectly shaven and smooth look overall… that just drove me wild and I wanted to be inside her right away.

Fucking A Dirty Sissy Girl

I stood up and pulled my thick cock out and pressed it against her dirty asshole while licking her neck, as she writhed, and moaned I could feel the rim of her asshole giving way, slowly gaping to allow me in. Then with a gentle push the thick plum shaped bell end of my cock was inside her dirty asshole having pushed past her rim, and she yelped with excitement. She was so tight that my cock felt like it was in a fruit press, but it felt amazing. Cherry whispered and egged me on saying “ fuck me bad boy.. dig into me deep you whore” she was erratic and talking nonsense as her caged cock and balls slapped back and forth, I even reached around and tugged on her cage to drive her wild. I was so horny I couldn’t hear anything... I lasted all of about 30 strokes inside her tight dirty asshole and then I unloaded a huge thick creamy cum load deep into her ass. It was all over as quick as that…the smell of her dirty ass now all over my cock as it hung wet and drained, I stepped back and pulled my pants back up. She slowly pulled her dress down and started arranging herself, she was no longer making eye contact with me... just meekly getting dressed. I said to her, “You go back to our seats first so it doesn’t look so hot when we both leave here together… and I will join you in 5 minutes” she murmured and left closing the door behind her… I relaxed as that awkward post climatic glow of a feverish fuck subsided and waited a full 5 mins before leaving the disabled toilet.

As I left the toilet, I looked towards our seats and couldn’t see her anywhere. I got to the seats and looked around, but could not see anything. Cherry was gone, I waited for 20 minutes before realising she was not coming back. I smiled to myself, still getting the faint waft of her dirty ass hitting my nostrils and downed my drink before leaving to head home.

To tribute my journey as an Alpha Master Mikey, click below.