Stephanie’s Toy

Anal

I think it’s something every man thinks about at least once in his life. What would it be like to wear panties? They are soft, silky… sexy. When I first started wearing panties, was just a couple minutes at a time. I would wear them around, check out how they made my ass look and then I would masturbate and fall asleep. Over time I became accustomed to wearing them and I got braver. I would wear them to the store, to run errands, and even to work a couple times. At first I took meticulous care not to get caught I would always wear another pair of men’s underwear over them and I would check constantly to make sure they were not showing. I was extremely paranoid and aroused. The pressure they placed on my penis and balls (and on my ass crack on thong days) made me constantly aware of them and made me think other people were aware too. But over time I became lax. I got use to wearing them everywhere and I realized that no one knew what I was doing.

In the summer of 2010 I slipped into a pair of frilly pink undies and headed to work like usual. I remember thinking to myself that morning that I needed to stop. “It’s no wonder you are 28 and single,” I told myself in the mirror. Really, my panty fetish had nothing to do with it. I hadn’t ever been close enough to a girl for that to matter. It’s not that I’m an unattractive person, just kind of small. And from what I gather, women like their men tall. My shyness and self-esteem issues didn’t help either. I parked in my normal parking spot and hurried to a meeting that I was already late for. During the meeting I daydreamed, like I always do, until some question brought me out of my trance. I stumbled through the morning in a daze mostly, making copies, answering question, pushing reports. It was all routine, and boring.

Around 10 or 11 that morning I was in the break room when the unthinkable happened. My button popped off my pants and they fell straight to my ankles. I struggled with my pants, trying to fasten them before anyone saw but it was too late. I hear a girly voice from behind me.

“Oh my God! You are gay,” she said.

I spun around to see Stephanie standing behind me. Stephanie was a 22 year old intern who had only been with the company a couple months. She was beautiful. I had been secretly harboring a crush on her but could never get up the nerve to talk to her. She had long blonde hair, bright blue eyes and a perfect figure. And at 5’3 she was one of the few girls who I was actually taller than. I watched in horror as this sexy bomb shell to pictures of me on her phone.

“I can’t believe this,” she said “Everyone tried to tell me but I just thought you were shy!”

“No, please” I stammered “I’m not gay. Please don’t tell anybody.”

She looked at me with amusement in her eyes “Maybe I’ll keep it to myself,” she Ümraniye Olgun Escort said “half laughing ” but what are you going to do for me?” she asked.

“I’ll do anything.” I told her” You want the job, right? Well I’m good friends with your supervisor. Ill make sure you get it but please just don’t tell anyone.”

She pondered it for a moment, “Well, that’s a start… but this is just too good. We are going to have to think of something else too. Where do you live? I’m going to visit you tonight.”

I reluctantly gave her my address and phone number. We left the break room and avoided her as much as possible for the rest of the day. I was a paranoid mess the rest of the day. I thought every time I saw somebody that they knew what had happened. Around 3 pm I received a text from Stephanie. It was a picture of a man in panties. The caption said ” I saw this and thought of you 😉 ” . I deleted it as quickly as I could and tried to get back to work. My hands were shaking so badly that I couldn’t type on my computer and my thoughts were so scattered there was no way I could concentrate. I told my boss that I wasn’t feeling well and took the rest of the afternoon off. I drove slowly to my home contemplating the horrors of the day and praying to God that Stephanie kept her word. By the time I got home I was numb. I sat on my couch in silence for several hours. I tried to calm myself down. “It’s ok, ” I said “nothing terrible has happened. Someone saw you in your panties and the world didn’t end. That’s a good thing…”

Around 6pm I received another text from Stephanie. “I’m hungry, have something ready when I get there. I’ll be over in about an hour.”

“K,” I responded simply. Dread welled up in my stomach. Over the past few hours I had nearly convinced myself that this had been a bad dream but then here I was, making dinner for the girl who held my life in her hands. She arrived exactly an hour later.

I answered the door to her after the first knock. As soon as the door opened she waltzed right in. “This is a nice place you got here, and man something smells good. I think we should eat before we talk business.” I felt my face pale. I stared at her blankly. “Don’t worry,” she said “I haven’t told anybody.. Yet. Fix me a plate please, I need to use the bathroom.”

For the next half hour we sat in virtual silence. The food was good, I know it was but everything just tasted bland to me. “Cheer up,” she told me “This isn’t going to be so bad, we are going to have fun. You’ll see.” The look she gave me almost made me believe her. After dinner we settled in the living room.

” Okay! ” she said excitedly. ” This is what I’ve decided. First of all, I’m going to be moving in. This internship doesn’t pay you know and my lease is almost up on my apartment. Ümraniye Sarışın Escort So before I leave I will need a key to our house. You can help me move this weekend. From now on you are going to be my little toy, to dress up and play with how I want. I expect you to do everything I say. Also, whenever we are at home I want you to wear those cute little panties you have, and no pants. And I think this goes without saying but if you piss me off or refuse to do any of these things then I’ll tell everyone at the office and ruin your life forever. Oh and I still expect you to get me that job, how does that sound?”

“I …” I stuttered. I really didn’t want to agree to any of those things but what choice did I have.” Okay, “I said “but if I do this, will you delete the pictures?”

“Umm, no.” she said. “Those pictures are the only insurance I have that you will keep your part of the deal. In fact I was thinking we might do another little photo shoot tonight. How does that sound?”

“No way!” I said “Then you will just have more blackmail to use against me!”

“Um, yeah.. ” she said ” that’s sorta the point. But come on. You know it will be fun. And plus, you don’t really have a choice.”

She was right about that, I knew. I slowly nodded my consent. “Okay, “she said. ” Lose the pants. You are not allowed to wear pants inside this house again!”

Slowly I un did my pants and lowered them to the ground. I was still wearing my pink panties from earlier. “Ugh! You need to take care of that.” She said, indicating my pubes. “I can see your pubes sticking out the top of your undies, not cute. Go shave that off then you’re going to show me the rest of your panty collection. I know you have more than one pair right?” I nodded and hurried off to shave.

Thirty minutes later I was clean shaven and back in my panties. “Much better,” Stephanie said “doesn’t that feel better?” she asked rubbing my cock through my underwear. “Now you can really feel the lace on that little dicky, huh?”

My cock grew under her touch, ‘Yeah..” I said to her “it feels better.”

“Good, now take me to the rest of your collection”. I showed Stephanie to my room and showed her to my underwear drawer. “Wow,” she exclaimed, “you may have more panties than me. Why don’t you try these on for me.” She said, handing me a blue thong. I slipped into them and stood for her to inspect me. “very nice,” she said. “Now try these,” she said handing me a pair of black lace panties. “Oh, I like those. Bend over for me so I can take a picture of your bum.” I stared at her blankly and didn’t move. I felt awkward being asked to pose in compromising positions. Stephanie sensed my hesitance and called me over to sit with her on the bed.

She stroked my arm and looked me in the eye, ” Look,” Ümraniye Şişman Escort she said ” I know you are feeling vulnerable and uncomfortable right now but if you just relax a little and try to have some fun I promise this will get better. Think about it. What would you be doing if I wasn’t here?” I thought for a moment before she continued. “You would be dressed up just like you are now strutting around by yourself. Isn’t this so much better? Getting caught may be the best thing that ever happened to you. Now you have someone who knows your dirty little secret and accepts you anyways. Now isn’t this better than masturbating by yourself into panties and falling asleep?”

I thought about what she said. She was right. I hadn’t really lost anything from this deal. The only thing that was different was now I had a smoking hot 22 year old girl to share it with. I was very nervous about the blackmail but she hadn’t asked me to do anything outrageous. And somehow the idea that I had to do whatever she told me to made it more fun. “Your right,” I said

“Good!” she exclaimed excitedly. “Now get over there and show me that ass!”

I walked back across the room and bent over so Stephanie could have a clear view off me. I heard the cameral go off. “Damn, girl!,” she said. “You’ve got a nice ass! I know girls who would kill for an ass like that.” I looked in the mirror and realized she was right. From the waist down I had a great figure. If people only saw my ass and legs I could pass as a girl easily. “Okay,” she said “Just a couple more shots and I’ll leave you alone for tonight.”

Stephanie picked out a couple more pairs of panties for me to try and snapped plenty of pictures. About half an hour later she was finished and I was allowed to pick out a pair to sleep in.

“Can I ask you a question?” Stephanie asked.

“Sure,” I said.

“When was the last time you were with a woman?”

The question hung in the air and I struggled to find an answer ” I… uhh…” I stuttered.

Stephanie’s eyes grew big as she realized what I was trying to say. “You’re a virgin!” she said “Now I get why you are so shy.”

“Yeah,” I replied.

“Okay, well let me ask you this, what all have you done with a girl?” Stephanie asked.

“Well, I made out with a couple of girls when I was in college and I ate a girl out one time, but I wasn’t very good at it.” It took all I had to answer her question.

“Wow,” she said “I am truly amazed. Okay well I’m going to get out of here. I’m getting tired. Try to get some sleep tonight.” After I showed her out I headed to my room and collapsed on my bed. I was drained. Emotionally and physically exhausted. I laid in the dark for a while thinking about my situation.

A little before midnight, my phone dinged, indicating that I had a message. It was from Stephanie. The message read “I hope we can keep this arrangement friendly but never forget that I have these. I own you ;)” Attached was a picture of me wearing black lace panties. The left margin it now had the caption, “Little girls love wearing pretty panties”

TO BE CONTINUED

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