Chastity Is A Confusing Kink

Chastity Is a Confusing Kink

This story has a slightly different presentation format. I hope you enjoy it.

I was born Jameson Madison. My name now is Jennifer Nicole Madison. I live as a full time female. The grip was tightening on me every day to become a woman, so I transitioned 2 years ago. My boobies are implants. I have had other surgeries to enhance my feminine appearance. I will stay a pre-op. I am a sex toy, and I love it.

I am kinky. I am naughty. I love boys and girls. I need both pussy and cock and yes, I am a good cocksucker as well as a terrific pussy licker. And I love my booty filled. I am still functional. I am a slut. I am submissive but have known to switch. Yes, you can also label me a sissy. I am the complete sexual package.

That leads to my love to play with sex toys, especially chastity. I own six different devices. My cock is not permanently encased in silicone or metal. In fact, I may wear one for only a few hours each day, or maybe not at all. Ten days is longest period that my cock has been caged but even then I experienced limited release.

Being locked in chastity is one of the ultimate services I can provide my partners. Wearing chastity is mostly a mental thing. It's all about entertainment and focus to me. I have had keyholders, I have self-locked. Chastity makes me concentrate on my partners needs and pleasures. It makes me pay more attention to my ass and how it feels being fucked. It makes the entire sexual adventure about me. Yes it really does. I love to top from the bottom.

And I will be the first to admit, it's all about me!

I enjoy wearing chastity cages because I want to. I willingly wear my cages. I have never felt forced to be caged. Chastity increases my desire to serve and service my partner. I am not currently in an exclusive relationship, and I have had multiple keyholders. Wearing chastity also humiliates me.

You Always Remember Your First Time

You always remember your first time but wearing chastity for multiple partners means you have many first time sexual events. My older sister, Melissa, was the first to demand that my cock to be encased in chastity, but to humiliate me even more, the person locking me was my ex-girlfriend, Aubrey aka Cash. I was fully aroused at the thought.

I will be brief, since my first time is documented in an already published story

Jennifer Nicole Goes Shopping

in the series

The Evolution of Jennifer Nicole.

The first time caged was to keep me from staining any new clothes that I going to try on during my first shopping spree dressed femme. So, Cash squeezed my shaft hard to break down my semi-aroused clit. Then did it again. It worked so she fit my shrinking shaft in the tube. She securely locked the rings and the shaft with the small lock. She kept the keys, sliding them down her gold neck chain that dangled between her magnificent globes. Later that afternoon, Cash freed my cock from the cage, then she expertly sucked it. I orgasmed very quickly that afternoon.

Being caged the first time, happened so quickly I didn't have time to balk. From that first experience, my curiosity about chastity became powerful. I was overwhelmed being feminine, but the chastity seed had been planted by Melissa and Cash. My mind took over from there, the desire to be caged again began to germinate. From that day forward, exposure to the mere concept of chastity kept running through my head. I tried to avoid the temptation, eventually the desire resulted in again trying on a chastity cage. The itch needed to be scratched. It was my cage to keep, so I self-locked whenever I felt the need.

I Didn't Have a Bucket List But I Had Two More Firsts!

So, then there was my first time in chastity with my girlfriend at the time. I also recall the first time I was caged for a man. Both times were with my college girlfriend Naomi. It was always entertaining to wear a chastity cage with her. Off and on we experimented with different sex toys, such as plugs, gags, collars, leashes, cuffs or remotes. Chastity somehow always was entangled in our play activities. Chastity has always been my favorite sex toy.

We also loved to share partners, male or female. Sometimes I was a Jameson but most of the time I was Jenn. We spent our college years sucking and fucking each other and others. If I was wearing chastity, Naomi would tease me building the tension in my loins. Having her mouth on my caged cock always rocked my world. When she released me, my cream always uncontrollably exploded everywhere. But Naomi loved to swallow, and we always shared my cream. Then she always wanted my cock inside her. We were young and she loved the penetrating sessions that always lasted longer and longer. We attributed the extended sessions to chastity.

But I always felt I needed more. So did she. One afternoon, she texted me to join her and her friend Hudson at our favorite coffee café near campus. Naomi, who is multilingual always wanted to text me in French. I took French lessons in school. It was our thing so to speak. It read,

'

Jenn je prends un café avec Hudson. Viens nous rejoindre.'

I responded back that I was a dressed as Jenn and self-locked,

'

Je suis habillée en Jenn, ça te va? Je suis aussi enfermé dans la chasteté.'

Her reply was,

'Hudson va apprécier ça!

'

followed by a smiley face with red hearts as eyes emoji.'

She never mentioned Hudson's gender only that Hudson will enjoy me caged in chastity.

When I arrived, I was pleasantly surprised. Hudson was handsome, with blond curly hair, nice smile, and a little hunky. When he stood to greet me, we hugged. He was taller than me, with a muscular and fit body.

Naomi, being Naomi, cut to the chase very quickly. "Jenn, Hudson and I have a design class together. He invited me for coffee and the conversation quickly turned to going out on a real date. I told him that I had a boyfriend and girlfriend!" She paused smiling, then added, "I told him that we shared!" Then giggled, "Hudson mentioned that he had experienced threesomes but never a foursome." Smiling I thought to myself, every woman would want to bed him.

Looking directly at Hudson I chuckled, "Did Naomi mention that I am

the

boyfriend and

the

girlfriend?"

Hudson smiled profusely, "She did say you were unique!"

It was my turn to smile, adding, "My house is nearby do you want a distinctive experience this afternoon?" I wasn't always this aggressive but wearing chastity always made me horny and I needed cock that afternoon.

Hudson first looked at Naomi, then back to me, "I'm game Jenn? You will be my first trans!"

Naomi smiling spoke up, "I am headed to the Boutique, I will reluctantly have to pass, but the two of you can manage without me. " She then looked at her phone, adding, "I have to run, or I will be late." Naomi squeezed my hand, we both stood to embrace, she whispered in my ear, "Girlfriend, he doesn't know that you are caged." Naomi hugged Hudson then hurried out the door to her car.

I grabbed Hudson's hand, leading him to the door adding, "Follow me Handsome!" Off we went to my house.

A Short Ride Then Surprise and Disappointment

In no time, we were at my off campus house. No one else was home, and we sprinted up the stairs to my bedroom. Once inside, I closed the door, Hudson pushed me against the wall. We kissed aggressively, just horny two horny college kids who couldn't get enough sex. I had his shirt off in no time, then quickly unbuckled his pants, dropping them to the floor. He was commando. His cock was aroused and throbbing. I dropped to my knees to begin caressing his cock with my hands and mouth at the same time. I wanted to suck Hudson's cock now, but he had other ideas.

He helped me out of my tee, revealing my black bralette encasing my breast forms. He then quickly undid my skirt's zipper, letting my skirt drop to the floor. He then stepped back, remarking, "I want to see what a girly boy looks like in panties!" Then his jaw dropped, smiling and staring directly into my eyes, he added, "I have never seen a cock locked up." He then caressed my locked cock and balls. I gasped at his touch. It wasn't rough but it was gentle either. I whimpered.

Hudson dropped to his knees, pulling my panties down my legs, ripping them at the seams, he continued to caress my locked cock with his hands. His soft caresses became rougher. He then unexpectantly kissed my cock head through the silicone shaft. I whimpered as he did. His mouth engulfed my caged cock. Just as quickly, he had other ideas, he grabbed my upper and lower torso, he picking me up, Hudson tossed me onto the bed.

He then pulled me by the hips back towards his throbbing cock. He spat on his fingers, then inserted two fingers into my butthole. I gasped. I pushed my ass back to greet his cock, Hudson pushed his cock in hard and fast, then suddenly he was smashing my butthole. I screamed as he entered me. His thrusts were rapid. My screams became louder.

Hudson then shrieked as he shot his load inside my ass. My screams turned to moans as his thrusts slowed down. His cock spurted again. He then stopped thrusting releasing his grip of my hips, I fell prone on the bed. Instead of joining me, he moved away to sit in the high back chair in the corner.

Rising back to my knees I could see his aroused cock throbbing. His cream filled my butthole. Hudson was the first to speak, "Sorry Jenn, when I saw your cock caged..." He voice trailed off, he then added "Sorry Jenn, I have to go. I will call you. " He slipped into his pants and loafers, holding his shirt in his hands, he left my bedroom.

Falling forward, I placed my hands in my face. I held back my tears. Sure, I had just been used, willingly raped if you may. I didn't understand what had happened that day, but I soon realized the impact and the excitement a man has when I was caged in chastity. I will never forget that day with Hudson.

He never called me, but I saw Hudson a few times after he was my first. Naomi always joined us; she always set up the threesome. He never said anything more about that afternoon at my house. Nor did I. He was handsome and hunky but never really satisfied me the way I wanted and deserved. To be honest he wasn't that good in bed.

I never saw him again after that. I don't know if Naomi did either. We never spoke about Hudson again.

My Chastity Curiosity Kept Me Locked!

While some men are able to reach some sort of satisfaction while wearing a chastity device, it depends on the device and the man's ability to stimulate various erogenous zones. I only wear chastity when I am dressed femme. I don't recall being caged in my male persona. Chasity devices are generally worn to prevent intercourse and other pleasurable sensations. I enjoyed wearing one as entertainment, whether it was self-amusement or the pleasure of my partner. I soon discovered that with certain partners my cock caged increased their libido ten-fold.

So, what does it feel like to wear a chastity device? A typical chastity device consists of a base ring that goes around the base of your shaft, fitting snugly above your balls. A tube of some type is inserted over your shaft. Any chastity device is added weight to your cock and balls; not necessarily a bad sensation, but it does feel strange until you get used to it. I prefer a silicone versus metal chastity cages. The silicone colors also help set my moods. I own a pink, black, blue, clear and one two-toned red and black. I own a metal cage that I rarely wear anymore.

The pink cage always brings out the sissy in me. The two-toned red and black the devil in me. The blue seems to bring out submissive persona. I don't know why it just does. When I wear the black cage I normally wear black lingerie, and the clear cage goes blends best with white. I prefer to be panty less if I am caged but sometimes my outer wear determines whether I wear or don't wear panties while caged.

So back to device details. The tube is designed to prevent stimulating your cock, thwarting full arousal and erection and of course other pleasures such as ejaculations. Or does it? Trust me no chastity cage that I have ever worn has kept me from creaming my load,

if and when your partner knows how to stimulate your prostate.

The first time your prostate is stimulated is euphoric, the next orgasm level is even more so, especially if your cock is caged.

My cock is aroused just thinking about all my other firsts.

First Time I Orgasmed in Chastity

So, then there is the first time your partner makes you ejaculate, and I do remember my first, of course I do. It happened at the gym.

I took at part time job at a private Gym in Riverdale. It was located a few miles down Route One, not far from the campus. Working at the gym gave me some

'WAM'

money - walking around money and a free gym membership. I worked the front desk a few nights a week. There were many regular members that I just waved through nightly. And I get some studying done between chores and member check-in. We closed at eleven, so I would normally lock the front door so I could go through my regular work-out routine before I headed home.

Tonight was no different. I wore sweats - top and bottoms most of the time, but I always was secretly femme underneath. Sports bra and tight Lycra short. As I go bolder, I would self-lock in chastity. That night I wore blue chastity cage to match my sports bra and shorts. The chastity gave me quite a bulge in my tight shorts.

I was about fifteen minutes into my regular workout routine when I heard one of the regulars, Mike O'Malley speak up, "Well, well, well what do we have here? Aren't you a little sissy bitch?" I was startled but at the same time I was trying to hide my bulge with the dumbbells. I wasn't very good at hiding my bulge.

Mike is very hunky and toned moved closer to me, adding, "What are you trying to hide Jamie? Either your cock is bigger than I thought, or you are wearing a sissy cage." Mike was a much bigger man than me; he took one of the weights away from me tossing it on the floor, then added, "Don't worry sweet thing, I am not going to hurt you. In fact, I like what I see!" He was dressed to work out, but I could see what the huge bulge getting bigger in his shorts. I was impressed.

I tried to be assertive, speaking, "Mike how did you get in here?"

Mike just chuckled, "The front door was unlocked, and I saw the lights still on, so I just walked in." I said to myself, '

Damn'

, I forgot to lock the damn door.

By now Mike was standing immediately in front of me, he remarked, "Jamie you sure have been hiding this girly boy look." He then leaned in to kiss me full on the lips, at the same time pulling my body into his. I could feel his now aroused cock against my stomach. I kissed him back. His hands grabbed my booty pushing my lower torso into to him. We continued kissing. His cock seemed to get bigger as he pressed against me. I love the feeling of a growing cock against my body.

I broke the embrace, shaking my head, I started to run to the front door, yelling back, "Mike let me lock the front door!" He waved me on. I quickly returned. By that time, Mike had removed his shorts, his huge cock was throbbing. I stopped in my tracks, just to stare at his rock hard cock. I licked my lips. Then added, "Mike your cock is good enough to eat!"

He just smirked, "Surprised bitch? Stop staring at it and start sucking it. Just suck it now sissy! " I immediately dropped to my knees. I wanted to hold his cock tightly and just suck it as told. So, I did. My mouth and tongue devoured his pulsating circumcised cock. There was no need to tease or lick his inner thighs. I went straight to the chiseled tip of his cock, twirling my tongue all over his cock head then up and down his shaft. I repeated and repeated my tongue twirls as I pushed my mouth down his shaft.

But Mike had a better idea. He pulled me back up to kiss me again, he placed his hands on the top seam of my Lycra shorts. In one full motion, he pulled my shorts down my thighs, stopping to reveal my cock bobbing back and forth in my cage. He was amused, as he cupped my balls and caged shaft with his enormous right hand. He squeezed my cage tightly, then said, "I want to fuck you Jamie, do want me to fuck you?"

I nodded my head, then mumbled, then softly screamed, "Yes I do Mike! I need your massive cock inside me now!" I begged him to fuck me.

I Became Mike's Bitch That Night and More

We both made our way to the high bench in the middle of the room. Mike pushed me down, I grabbed and held tightly to the sides of the bench. Mike spread my legs; I arched my back pushing my booty into the air. He squeezed my chastity cage again; I was leaking profusely. I filled his hand with my precum. I heard him spit into his hand to add more lubrication to my butthole. Mike squared me up gently pushing his cock head into my anus. I screamed as he entered me, the screams turned to whimpers to more whimpers.

My hip and ass movement matched his thrusts. His cock head was large but narrowed into a long shaped cock. He went deeper into my butthole than anyone before him. My whimpers turned to louder moans. Mike was finding sensitive spots in my ass that I didn't know I had. I gasped with each stroke. I tried to maintain my breathing. Mike's cock found my prostate. My body began to shake all over. I grasped the bench harder. The sensation inside me was something I had never experienced before.

He forewarned me, but it did no good. Mike shot his load inside my booty, not once, not twice but three times. Each time I screamed in pure pleasure. Each time my body shook. It was amazing how I shook each time he ejaculated inside me, then to my compete surprise my cock ejaculated spewing my cream all over the bench, my chastity cage and my lower stomach. It was intense. My body tumbled onto the bench. Mike held my hips to keep me from falling on the floor.

His cock was still throbbing inside my butthole. He slowly pulled out. My shakes became intermittent finally calming. I have never before experienced that sensation.

Mike picked me up to embrace me in his arms. I swallowed hard, then mumbled, "Wow that was intense. What did you do to me Mike?"

He stared into my eyes, adding, "I found your prostate Jamie. I assume no one has explored your prostate before. " I shook my head no. Pausing he added, "Let me give you an anatomy lesson. Men have a P-spot, just like women have a G-spot. You prostate is an almond-size gland that sits about 3 inches inside of our butts. When its stimulated you experience a full body orgasm like a woman! " He smiled, then added "I love it!"

I kissed Mike on the lips, then whispered, "Mike, thank you for that!"

Mike looked at his watch, "I better get home. I want to fuck you again Jamie... if you are game?" I nodded yes. And we did off and on for several months. Mike was married, a gym regular, and apparently knew my schedule better than me. We didn't fuck every week, but he was inside me frequently. He always showed up just before closing and each time he rocked my world. I always wore chastity for him and almost always creamed myself. I wore different color cages for him. He bought me a yellow silicone cage. He is a Steelers fan. Somewhere along my travels I lost his gift. Yes, I always wore my sports bra and tight shorts for him. He loved my booty, literally and figuratively.

At the end of the semester, I moved back to Annapolis for the summer. In the Fall, I didn't return to work at the Riverdale gym. I didn't see Mike again. I lost touch with him. I will never forget Mike. I was his bitch that semester. He was another enjoyable first for me.