Training the Sissy Pt. 01

(Sissy) Training

Part one "On display"

I had been working late yet again. Still, I tried to get time to do some training at the all-night open gym next door. It has an unmanned security gate with a fingerprint reader so the customers can come and go at any time.

I had been going to this gym for about 6 months now and it started to show. I am a bit below average height and slim built, but with the weekly training I was at least getting some muscle tone in my legs and my stomach was getting flatter.

There was usually no-one working late at night, but sometimes Bobbie was hanging carelessly behind the reception counter. The first time I met Bobbie I actually thought she was a "he" called "Bobby". She could easily pass for a slim built male in roomy jogging pants. Later, when I met her in a sport top and compression training pants there was no doubt the name was Bobbie and that she was a girl. She had short black hair and muscular arms. She was not the body builder type but seemed to be more into aerobics. Her breasts were small but looked firm and her ass was not too flat and muscular but jiggled slightly when she walked. She was good looking, that's for sure but she never paid any attention to me. People seldom do. So, we just nodded to each other, at best.

One night as I walked past the counter I stopped and looked at the new clothes exhibition that the management had started showing in the entrance. There were various sportswear on display and my eyes could not help but look at the women's part of the rack. I daydreamed a while hoping to one day get a girl that fitted into beautiful training panties and bras that hung there. I especially enjoyed looking at a pair of white panties, a thong with a sports brand on it. I imagined it fitting tight over a toned feminine body with a bit of the ass-checks showing and just slightly cutting into the soft flesh making a line up to the waist.

Suddenly, I felt I was being watched. Out of the corner of my eye I saw Bobbie coming out of the back office. I had not known she was working tonight. I quickly turned my eyes away from the clothes and scuffled to the door. Letting myself out through the self-service gate.

...

A couple of nights later I was, as usual, working late. It had been dark for a while as I made my way through the security gate to the gym. Bobbie was at the counter, and even though she did not say anything, I felt as she was eyeing me as I passed. But I thought I must have been imagining that. She never paid any attention to me.

I did my usual workout, trying to strengthen my weaker body parts. When I got out of the shower and finished drying myself with a towel, I noticed a package laying on the bench where I had laid my clothes. Curious I picked it up and found that it was a pair of the panties I had looked at a couple of nights ago. Someone must have bought them and forgot them there, but why in the guy's locker room?

After a while I was realizing I could not take my eyes of them and wanted to have a closer look. I carefully opened the package unfolding the smooth and flexible underwear.

Why was women's underwear so much softer and more likeable than men's underwear? I had always wondered but never dared to take a closer look. I had no sisters and my encounters with girls had been more of a random and quick nature. Suddenly I realized that I was interested in how they felt if I put them on. I breathed out slowly finding this new part of myself. It tingled in my stomach and down to my sensitive areas. Silly boy, I thought, what's so special about a girl's panties? Only pieces of cloth like men's underwear?

Without making a conscious decision a looked around and started slipping them on my already naked body. They felt smooth as they passed my legs and when they brushed my sensitive parts I gasped a little from the unexpected feeling. After trying to get them to fit comfortable around my ass I found that they were tighter than my usual underwear, pressing at my penis and cupping my balls. It felt so different. I felt weaker, softer and more vulnerable. Why was that?

To my left there was a full-length mirror and when I started to slowly look into it from my feet up, it seemed that I was looking at a girl's legs and panties. I had a slight bulge, but it was not so visible as my package was not all that big to begin with. I could not help turning around looking at my ass, which was tightly packed in the white panties. I was getting hard, which surprised me.

Could I get hard just from watching a guy in panties or was it something else? Did I imagine I was seeing a girl? Suddenly I felt very self-conscious and embarrassed. I quickly slipped out of the panties, stuffed them in a trash bin and put on my usual clothes.

When I exited the building, there was no sign of Bobbie, lucky for me I thought as I imagined how my guilty face looked as I went home thinking about what had just happened.

....

I was a bit reluctant to go back to the gym for a couple of days. Why did I put those panties on? Was I gay? I had always been sure that I liked girls, even though I had not had a long-lasting relationship.

I realized I was being silly, no one had seen me, and I really needed to train. I had paid for the full year membership and wanted to use it. So, the night after, I went to the gym and did my usual routine. No sign of Bobbie or anyone else. In the shower I had a quick thought about the panties from last time, which gave me a slight tingle below the waist. I had the feeling I had found a treasure but then thrown it away. I was lost in thought leaving the shower.

I had just got my boxers on when a voice behind me suddenly said:

"It was not nice of you to throw away my gift."

What? I spun around, only to find Bobbie standing in the doorway of the men's locker room with a smirk on her face.

"What do you mean," I said with a slight panicked tone in my voice.

"I saw you eyeing those little white panties and thought you might like them, and I was right."

"Wh...what?" I stuttered.

I was getting terrified, and she seemed so self confident.

"Oh, you know what I mean. We had cameras installed here for security reasons, you know, and it's all on file"

"I.., I never, you cannot show that to anyone!"

"Why not? Are you afraid someone might think you are gay? I have all your info on file in the reception, I even know what company you work for...an upload to YouTube and a quick e-mail is all it takes..."

As she said this, she slowly approached me, keeping my eyes fixed. Today she had tight yoga pants which showed her muscular hips and ass. A black nylon trainer top and a cap made her look really sporty. I was feeling a weak sensation in my knees.

"I...I'll do anything, please don't send that to anyone...how much do you want?"

"Oh, I want it all..." She said without taking her eyes off me.

"Ok..." I hurried to my locker, fumbling as I tried to find my wallet."

"No, no, no...money is not what I want, at least for now...no I want you to accept my gift..."

"What gift?" I said, fearing the answer.

She took out the white thong panties from behind her back.

I could not say a word.

"I know you like it, now but them on...sweetie."

"No, I...I..."

"Shhhh", she put a finger on my lips, and I felt all weak inside.

What was she doing to me? I realized my options were few, so I reluctantly took of my boxers and put on the panties. I got the same tingling sensation as the soft fabric brushed over my sensitive areas.

"That's right. Doesn't that feel good?" She cooed in a soft voice.

"Now, let's walk."

She ordered me to step out of the locker room, when I protested, she smacked me lightly on my ass, reminding me of the video she had on file.

She led me to a room that was used by the physiotherapist and ordered me to get up on the massage table.

"Get up and stand on all fours. Arch your back so I can see your little ass in those tight panties."

I was really embarrassed as she got me to behave really girly. At the same time, I had given up resisting her in some unconscious way. I felt powerless. To top it all, my penis was getting hard inside the white smooth panties, straining against the fabric.

"Now lay down on your stomach and I'll begin to treat your condition."

"Condition? What do you mean?"

"Shhh," again her finger softly touched my lips and slipped in briefly into my mouth.

"You will soon find out."

She began oiling up my back and massaging me slowly. It was not unpleasant, but I had no idea what she was going to do, and now I could not see her either.

Suddenly her hands reached my ass and started massaging my ass with strong hands. After a minute or so she started to run a finger over my asshole, caressing it through the soft fabric.

"Ooo, this seems warm and soft, why don't we slip these tight, white, girly panties off."

Even though she had forced them on me I was reluctant to leave my last piece of clothing, but I could not argue. She continued caressing my ass and then her tongue started trailing down my crack as she breathed out heavily.

"You are so smooth down here, almost no hair...like a real girl."

And then she reached my asshole. Her tongue was moist and warm, but it felt weird having something up there moving around. I tried to turn, but she put one strong hand on my back showing me that it was no idea to argue.

"You are really such a slut, this feels so soft and willing. I know what this sissy needs."

She got up and smacked my ass again. It hurt a bit, but I was also humiliated. Spanked by a girl and laying helpless for her to do as she wished. But I did not dare to move.

"I got something here that will make this easier for you...now just relax."

I felt something hard and cold moving up and down my crack, oiling it up. Was that a dildo? What she really going to...

"Anggh!"

She started pushing the dildo into my ass. I had never done anything remotely like that and it felt really strange. It hurt, but as she moved it slightly in and out the sensation got more and pleasurable.

"See, you're a natural sissy slut, just as I thought when I saw you looking at those panties."

"Annghh." I could not answer that because she had just inserted another inch and I was concentrating on dealing with that new sensation.

"Now up on all fours so I can see your whole sissy body."

She smacked me lightly on my ass and the steady movement in and out of my sensitive hole continued.

I got up on all fours, realizing that my dick was hard and there was probably precum dripping on the table.

"Yes I thought so...all exited and ready."

I could not believe that my body was responding to this, but the more I got used to the pressure from the dildo the more pleasure I was starting to get from it. That really made me even more ashamed. I was being fucked in the ass by a dominant girl, standing on all fours...and liking it!

"ohhh, so wet."

I felt the tip of a finger moving around the tip of my penis. She pressed my foreskin and tip together with two fingers gathering as much pre-cum as possible.

"Here, have a taste. It's probably delicious."

With that she put the two fingers into my mouth, and I could not help but taste the slick fluid. I moaned as she moved the fingers over my tongue and a couple of times in and out of my mouth, finger-fucking me slowly.

The sensation of having her fingers in my mouth and the dildo going in and out of my ass was so overwhelming that I came without her even touching my penis.

For a long while I felt like I was floating, moaning, and shaking on the massage table. It was the most powerful orgasm I had ever had. Then reality came washing back over me, and I realized I had come on the massage table and now stood on all fours with a dildo in my ass.

"Wow, you came without me even touching your little dick."

"Anngh..." another moan from me and a soft laugh from her as she took out the dildo from my ass.

"I knew you would like it, you're such a pretty slut."

She scooped up some of my cum from the table and then pushed two fingers into my mouth, moving them slowly in and out.

"What a nice mouth you have, eager to please...but that's all you'll manage for tonight. Now clean this mess up and come back on Thursday night. Don't forget to bring your panties."

As she left the room, I wondered what had just happened to me and what would happen next?

To be continued?