Training the Sissy Pt. 02

Part two "I was not ready, or was I?"

I was in chock after my meeting with Bobbie in the gym. After a week I still found it hard to concentrate on work. And I had not dared going back. Had Bobbie forced me to put on those panties or had I secretly wanted to do it all along? I was not sure. I could not help myself getting hard every time I thought about it. Being in that room so exposed, helpless, unable to move. Not that Bobbie had restrained me, it was just a feeling in my knees, getting weak, and my arms being hard to lift. I just wanted to lie there, face down, while my ass was being penetrated.

I snapped out of my daydream, realising I had not gotten anything done for at least half an hour in front of my screen. It was my phone, someone texted me. I had very few friends, so it was not very common to hear that sound. I looked at my phone and the message made me sweaty, and my breath got more shallow

"Hi, you know who it is. I know you are sitting there thinking about what happened."

"Remember, I have all your details in the gym database. You are not being a good sissy boy by not coming back to see me. I will be there on Thursday evening, put on those white, tight panties and come. I know you want to."

That was all it said. How could she know? Was it that obvious? I was now aware of the bulge in my underwear. I was clearly excited, and I could not help thinking about those white, soft panties. I had put them in a drawer under some other stuff, but I wanted to go home and look at them, run my hands over the smooth material. Did I dare put them on again? Where was this taking me?

I could not concentrate on work, so I closed my laptop and went home.

...

On Thursday I was still no sure if I was going to the gym. I was afraid. I could get caught in some way and I felt ashamed of my feelings. And Bobbie was a bit intimidating. I was not sure who she was or what she wanted from me. I looked at the panties. I could not help myself; I was going to the gym. I was going to give them back and tell Bobbie that I could not do this anymore. I grabbed my gym bag and put the panties carefully into the bag. God they were soft!

...

At the gym there was no one in the reception. Strange, maybe she was tired of waiting for me or it was all just a trick. Well ok, I needed to exercise anyway so I went to the locker room and changed. She could not stop me; I was a member and had every right to use the gym.

I trained with great energy. No one could tell me what to do! As usual I spent extra time on my weak parts, my belly, and my legs. I was working on my triceps when I started looking at myself in the mirror. I did have a round, nice ass. Especially when I was standing on my toes. If I looked only below the waist, from behind I could almost see a fit woman.

What was I thinking! Where was this coming from? Bobbie had messed with my head. I was a boy, a man. I stopped my training and went to the showers, angry with myself for being so easily manipulated.

After getting all the sweat off and using my favourite body wash, I felt much better. I went to the locker and opened the door to get my clothes.

"I like what I see" a low voice said behind my back

There she was, resting against the door post. Bobbie was wearing skin-tight green yoga pants, showing off her muscular body. She had only a matching green sports bra as a top but she still had lots more clothing on than I.

"What do you mean?" I said trying to sound confident, but my voice was unsteady.

"I like what I saw in the gym, you working those legs and your ass, and I see you now, naked and ready." She said with a smirk that made her look hungry.

I covered myself with my towel gathering what courage I had left.

"I only came to return the panties; we cannot do this anymore." I said not sounding as confident as I had hoped. I started looking through my bag to find the panties.

"Do what anymore?" Bobbie said, taking two steps closer.

"I, I mean we..." I stammered, but my words felt like they were stuck in my mouth.

"We have almost done nothing at all, you just had a treatment in the massage roomt the last time, remember?"

She took two more steps, closing the distance between us. She showed her right hand that she had hidden behind her back.

"Are you looking for these?" She showed the panties, giving a little wave.

"There are no secrets here my sissy boy. I know what you need."

One more step and she was so close that I could feel her body warmth and smell her scent. It was a bit musky, like someone that had trained and not showered afterwards. But not unpleasant. I felt myself loosing control and my cock was making a bulge under the towel.

"So, I see that I was right, look at that, springing into action." She said giving the lightest touch with her fingernails over the towel, just barely touching my penis through the fabric.

I felt like I was being electrocuted and my body twitched from her touch.

"OK, this is what we are going to do. I will leave you here with these soft, tight, white panties and wait for you in the massage room. If you come you will do as I say". Each word was said with slow determination, like nails being pounded into a plank.

She put down the panties carefully on the bench, bending down showing me her tight muscular ass. The yoga pants were really hugging her round features and I could almost make out her pussy as a slight bulge for a brief moment.

She gave me a knowing smile, turned, and went out of the locker room with the confidence of a lioness after the hunt.

I sat down, breathing shallow, trying to think about what to do. My body was clearly on board, but what about my mind? Was I ready to go further with this? What was this, I had never thought I was a deviant of some kind, dressing up in girls underwear. Where was this coming from. Or had it been there all along?

Well, there was no turning back. I dried myself completely and slipped on the white panties. God, they felt nice. After slipping over my knees I felt the softness moving up around my legs, finally cupping my balls and penis tight. I could not help myself and ran my hands over my ass, feeling the smooth, round tightness over my sensitive skin.

...

I opened the door to the massage room. Bobbie had lit a few candles and I was glad that the hard fluorescent ceiling lights was not on.

She was sitting in a leather chair resting, legs crossed. The massage bench was set low, maybe 40 centimetres above the floor.

"I knew you would come. Sissy boys can't resist putting on their panties." She cooed smiling knowingly.

"Lie down on your back and close your eyes." She commanded.

I did as I was told. Breathing out, breathing in. What was going to happen?

She moved around in the room and after a short while I was feeling her fingers lightly brush my legs up and down.

"First you need to relax." She said.

"I want you to be completely relaxed."

She continued with those light strokes, moving up my body, clearly avoiding my genital area. When she reached my chest, she gave some extra attention to my nipples, which I knew from before was very sensitive. I felt my penis getting hard.

"My, my, sissies are always so sensitive there." She laughed a little bit pinching my nipples slightly.

She continued rubbing her palms over my nipples moving her mouth just close to my ear.

"I know what you want. " She whispered.

"I know what you need." And with that, her tongue slipped into my ear.

I had never had a wet tongue in my ear before and it was more intimate than I could have imagined. She licked and tickled my ear, breathing heavily and at the same time continued working on my nipples. I was writhing on the massage bench, having a hard time keeping still. At the same time wanting to get away from the intruding tongue and still wanting more.

"I see you are getting wet." She whispered in a hoarse voice.

"Let's see what we have."

With that, she pulled down my panties so the tip of my penis was visible and squeezed the top with her index finger and her thumb.

"Oh, yes. So much pre-cum. Taste it". She said and put two fingers in my mouth.

I could not help myself anymore. I licked her fingers tasting the salty flavour of my own clear pre-cum. I wanted more.

"Now, now. Don't be greedy. There will be more to come." She said with a stern tone.

"Now, keep your eyes closed and turn over."

I did as I was told. Having a hard time placing my semi-erect penis under me.

For a while I just laid there. Bobbie was doing something behind my back that I could not make out. Then she was behind me, coming up over my legs. I felt her hot breath against my ass.

"It's time to take it to the next level my sissy boy. Just relax and let it happen."

She breathed out and I felt her tongue circling my ass-crack. Trough the thin satin fabric of the white panties. Slowly she pulled them down, exposing my ass and it felt like my inner self was being exposed. I was totally helpless feeling weak and accepting whatever was going to happen next.

She used her tongue on my ass moving up to the sensitive spot on my lower back and then again down my ass using her hands to get access to my asshole.

"Yes, you are so soft and girly down here. Almost no hair, round and smooth." She cooed.

She was using her fingers now and I felt the slick sensation of lube being massaged into my asshole. Was she going to use the dildo on me again. I was afraid of that at the same time I wanted it. I needed it. I could not shake the sensation of something big going in and out of my sensitive ass.

Suddenly she stopped. Not going in with a finger like last time. I was surprised and ashamed of my thoughts, my needs.

"Up on all fours, keep your eyes closed." She commanded.

I did as I was told.

"Now, open your eyes my sweet sissy boy".

I looked up. She was standing in front of me, triumphant, wearing her green yoga pants and her sports bra. But what caught my attention was the big smooth strap-on dildo very close to my face. It looked like it was 7-inches long, longer than my penis at least.

"I see that you like what you see, now try out how it feels being a helpless sissy." Whit that, she gently inserted half of the strap-on into my mouth and just stayed there.

"Yes, get used to it, this will not be your last time sucking a dick." She sounded very pleased with herself.

Slowly she started pushing the dildo in and out of my mouth and after a while I got used to the feeling. It was exciting. I could see here pumping her hips, very confident and clearly in control. She had definitely done this before.

"See, you can almost take the whole 7-inch cock right into your mouth. Don't worry sweet sissy you will get more training so you can take all of it, and more." A little laugh escaped her. It turned me on even more.

"Ohh, you are still leaking pre-cum, and much of it. Let's see what we can do with that."

She reached out and scooped up as much as she could get, putting it all over the strap-on

"Let's see how you like the taste like this." She said as she re-inserted the strap-on into my mouth.

I could feel the slick pre-cum coating my mouth and the taste was different now mingling with the taste of the strap-on. That, together with sight of Bobbie smiling at me, pumping her hips and the smell of her body so close was too much. I moaned into the dildo, not thinking about what I was doing any more.

Bobbie lowered herself over my back so I could feel her sports bra barely touching my back. I thought about her small, perfect breasts within that tight material.

Suddenly I felt her finger entering my ass slowly. The feeling of having something in my ass, at the same time having the strap-on in my mouth was intense.

Bobbie entered with another finger, and I felt my body tensing up and my penis doing something I had never experienced before. I came without myself or anyone touching my penis.

"Yes, yes, oh what a great sissy you are going to be, coming without even touching yourself just from being fucked in both your holes." Bobbie exclaimed sounding very pleased as she withdrew the strap-on from my mouth.

I could almost not keep myself up on all fours on the massage table, being exhausted by the experience. Bobbie scooped up the cum from the table and put it on the strap-on.

"Lick it clean, dear sissy, before it gets all could and sticky." She said with a stern voice.

I did as I was told. It was not as bad as I thought it would be. It was slick and creamy, and I knew it was connected to my experience. I was ashamed, excited, and exhausted all at the same time.

"Now, rest a while. We are not done quite yet." Bobbie said letting me lie down on the table.

What was going to happen next?