Journey For Sexual Freedom

by Jackie Boy

23 Nov 2023 3108 readers Score 9.0 (31 votes) PDF Mobi ePub Txt


For the last 15 minutes, I have been sitting in my car in this dimly lit parking lot. My hands are shaking in fear, but I’m trying to psyche myself up. I’m not backing out this time. I’m going in.

I stared at the entrance and waited. There were barely any cars in the lot, and I thought maybe the place was closed. It was dark out but it was only 6PM. Stupid daylight savings. That’s it, I’m going for it. As I grab my keys and head towards the door.

I approached the door to a sex toy shop somewhere in New Jersey. I just dropped my girlfriend off at the airport and figured this is the perfect time to try out some toys. I never owned one and was always interested in exploring. However, she is very vanilla when it comes to our intimacy.

Plus, I recently got sucked into watching sissy porn and hypno as a dare to myself. I always liked to dare myself or punish myself in strange ways ever since I was a kid. I’m that kid that would have rubber bands on my wrists and snap them every time I did something wrong or stupid. The dare was that I could watch 30 minutes of hypno one time to prove to myself that its not addictive. I know hypnosis doesn’t work, however addiction is another thing. So I did watch it that one time about a year ago. Now, its one of my go to porn genres when playing with myself. Whoops. However, its all just play. I’m still Jack a straight 23yr old with a hot girlfriend.

My plan was to buy a dildo and maybe a butt plug. Just some nice starter toys. I had 2-weeks before I had to pick her up. I had cash in hand and choose a nice store far from home. I also made sure it was not some sleazy truck stop adult store. I heard some scary tales.

As I entered, there was a nice clean and well lit atmosphere. This just looked like it could be a normal shop except for the walls and walls of dildos, plugs, lubes, dvds, and lingerie. There was a lot to take in and the store was bigger than I thought. I really didn’t have a set list to buy where I could grab everything and sprint back to my car.

I really wanted to turn around and bolt for the door. I was about to run until a man near the front counter said, “I see you finally decided to come in. Let me know if you need any assistance.”

I blushed and nodded.

“First timer?” he asked.

“Yes sir.” Oh shit. Damn my manners. I can’t believe I just called a stranger sir…in a sex shop...within seconds of entering. I blush harder.

“Excellent. We have a special discount for first timers. You just need to ring that bell and you get 20% off.”

I always love a bargain but the bell was big and shiny and I’m sure very loud.

“Don’t worry boy. The store is empty, no one will hear it.”

I blushed again at him calling me boy. Sure I’m on the younger side especially to this 40+ year old man (maybe). I’m just 23 years old and barely 5’7” and on the slim side. I’m fit but my genes never allowed for much in muscle mass. Just enough to look like a well toned feminine body. I really hated my build but its a small trade off for good looking skin, straight teeth, and silky hair to my shoulders.

I ring the bell and it echoed through the whole store.

“Good job boy. Let me know if you need anything.”

He continued on with his task and I walked towards the back of the store passing by racks of DVDs and magazines. I can’t believe magazines are still a thing. Next up was some really cute and sexy outfits. I slowly walked through here. A few items caught my eye. I would love to see her in them but I know she would never put them on for me.

Next section was the dildos. This was what I came for. However, I was not expecting this much variety. My eyes were big like a deer in the headlights. Where to I start looking? There must be dozens and dozens of options. Sizes, shapes, colors. I don’t know how long I just stood in the middle of the section but it must have been a long time.

All of a sudden, the man comes up behind me and places his hands on each of my shoulders. He was almost 6 foot tall and had the typical body of a 40 year old sleaze I would expect to find working at a shady truck stop adult bookstore. Not in a place like this. I could feel his beer belly touching my back as he says into my ear.

“You ok there boy?”

Shocked. I blurt out, “I don’t know which one I want?” Oh no, I already didn’t want to talk to someone in the store. Let alone tell them I was buying stuff for me.

He starts to massage my shoulders. “Don’t worry. It is overwhelming. Maybe I can help you decide. Tell me what are your plans?”

I was answering his question in my head to see if I can rephrase it so it wasn’t too weird. Well I thought I answered it in my head.

“Well, my girlfriend is out of town for the next two weeks and I always wanted to explore playing with toys. I really want to simulate what its like to suck a cock. My gf hates it and always complains. So I want to see if she is right. I guess that goes with anal too.” I giggle.

“Thats a common story we here. I got you. So, first off you should start off easy. So stay away from these 10+ inch options.” As he grabs one and points it inches from my face. My head slightly leans back.

“I would say anything with a realistic label on it and of course a suction cup. If you want to simulate what your girl friend feels, may I ask your dick size?”

“Um, average I guess.” I blush at telling a stranger my cock size.

“You don’t sound so sure. No worries we will just start with this one. This is average.” As he picks up a 6in flesh colored dildo with tons of veins and a well textured ball sack. If this was average, I hate to hear what mine is. This looks like a good inch, maybe inch and a half, bigger than mine.

He drops it into a shopping bag and hands it to me. Next I feel him guiding me through the store.

“Let’s see what else you need. Hmmm.”

He just started doing the shopping for me. We went from section to section. In a few seconds he had filled half my bag with some starter plugs, beads, and lubes. Im not sure, I was in a daze. My mind wasnt ready to process the change in situation.

“Um sir. I don’t know if this all necessary. First I don’t know if I have enough money for all this,” as I pull out a wad of $100. “Plus, what if I start to use it and cum quickly and do that whole shame reflecting I hear about and throw this all a way?”

He grabs the money from my hands. “I’ll make this enough. As for the cumming early part, there is a solution for that.” He leads me into the BDSM section which was in a separate room. This room had some menacing looking devices. I’ve seen some in pornos but there definitely was a few that I didn’t know, or even know how they would work.

As I was looking around, I didn’t notice that he took me to a shelf full of chastity cages. “These will make sure you don’t cum early.”

They were all over my allowed spending limit, even if I put all the toys back.

“Don’t worry about the price. I’ll make you a deal.”

“Um ok”

“I’ll give this to you for free, only if you let me put it on you and lock it. I’ll give you the key and use one of the Fedex overnight envelopes we have up front. People send out their keys all the time from here.”

“What? I don’t know, having some stranger dude fondle me is like out of my comfort zone. I’m not gay or anything.” As I look into my shopping bag full of evedince that would say otherwise.

“Come on think about it bro. No chance in cumming until tomorrow. This allows you to really explore.”

I felt myself getting hard. My blood flowed away from my brain into my twitching dick.

“You said free? You just will touch my dick like a medical exam right? No weird funny business.”

“None.”

“Sure why not. One problem, I'm hard right now though. I guess that's an issue.”

“Wait right here. I have something for that.”

As he walks away, I walk around the room looking at the bdsm inventory. I gravitated towards the mouth gags.

The man comes back with two cold cans of soda.

“Ok, time for you to drop your pants.” As he pointed to an exact spot in the room for me to stand. (Not knowing it was the best view for the cameras to see.)

As I dropped my pants, I could feel his stare burning a hole in my cock. I felt it twitch.

“Meh, its almost close to average. Could be worse.” He laughed as I felt the cold soda cans which must have been in the freezer because they were super cold. The icy sensation shot sharp jolts through my body. I could feel my tool shrinking and going soft instantly.

“Oh god” I moaned. My knees buckled.

And just like that I heard two quick clicks and a sudden weight pulling on my limp dick. Just like that he forced me in and locked it up. He gave the cage a friendly slap which caused me to let out a deep moan.

“All done boy. The name is Tony by the way.” Oh my god, I just let a strange man touch me and I never asked for his name.

With staggered breaths, I try to form a snetence. “Hi, glad to meet you. My name is…”

“”I don’t care what it is slut.”

He took the key upfront and just left me standing there with my pants around my ankles holding a bag of sex toys.

I didn’t snap out of it until I head the bell ring indicating another customer came in. I quickly pulled up my pants and rushed out the door with my kinky haul. No need for a receipt, I just had to get the hell out of there.

I drove straight home which ended up being bumpier than I remembered. Or maybe its because I feel my enclosed penis dangling from side to side. Every bump send shivers through my groin. Within a few miles, I noticed a new strain or discomfort. I was trying to get hard. Trying was the key word. As I drove, my hands kept fiddling with the cage as I tried to get use to it.

As soon as I got home, I quickly tore off all my clothes and stared at myself in the mirror. I just stared at my near hairless body in the mirror. I fondled the cage thinking it would help the pain, but it made it worse. My fingers rubbed the enclosure as I felt the steel against my shaft. I then was inspecting the lock. Tugging on it to see if it was a legit lock or some cheap plastic one. No this one is the real deal.

“Fuck!” I just realized I ran out of the store and never gave the clerk my address or grabbed the key to the lock.

I quickly grabbed my phone and called the store. It felt like it rang for an hour before a machine picked up. Noooo, they are closed now. Oh god, what are the hours for tomorrow. Oh god please machine tell me.

I was literally whimpering and pleading into the phone to an automated message. It didn’t care. Every time I spoke it thought I was activating some menu and said there was an error and it started all the way at the beginning. Every time it restarted its message, my cock tried to swell beyond its restraints, which caused me to shake, gasp, and moan in discomfort. I was so hysterical that I didn’t realize it was doing this for almost 5 minutes. I finally shut my mouth and paid close attention. It slowly went on with its spiel of sales and locations. Fear in my eyes along with some tears.

Tomorrow is Monday, so Im hoping they open around 9am. Oh finally, here are the hours. Hurry up machine.

“Our store hours are Sunday 10a-8p. Monday we are closed. Tuesday through Thursday…..”

I dropped my phone. Did it say they were closed. Oh my god. What have I done. Naked and now afraid, I dropped to the floor and started to cry.

What will I do until Tuesday? Whimpering and laying on the floor naked, I see the bag full of sex toys I just bought.

by Jackie Boy

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