My Life As A Panty Sissy Ch. 01

"Jason." I heard her say, snapping me back to reality. "You're almost there, Sweetheart. Just take your shorts off and hand them to me."

I'm not sure how I managed it, but, I did as she asked. I hooked my thumbs into the elastic waistband of my shorts and I pushed them all the way down. I couldn't look at her as I bent down and picked them up off the floor and held them out. My body was flushed with humiliation and embarrassment as I stood there, and when I felt her take the shorts from my hand and toss them on her bed, the soberness of my situation kicked in and I realized I was standing in front of my mother wearing my sister's pink, frilly panties.

Almost as soon as she took the shorts away from me, I felt her hand on my chin, tilting my face up to look at her. When we made eye contact, she said, "Look at me, Jason. Don't look away..... look right into my eyes and keep looking at me."

She held my stare perfectly and after fifteen seconds or so, she said, "Just stand like this for a minute and keep looking at me. Relax and take a few deep breaths, Sweetheart. You've done good so far. Don't ruin it by doing something senseless."

We stared at each other for over a minute, and during that time, my breathing calmed down a little and the pounding in my chest subsided. "Keep looking right at me." She said again. "And, I want you to listen to what I'm going to say. Can you do that for me?"

"Yes." I croaked, barely able to talk.

"Alright then, now listen carefully." Mom replied. And then without breaking the stare between us, she started to speak.

"It's perfectly okay for you to wear panties from now on." Mom began. "And, it's okay for me to see you wearing them. You don't have to hide it anymore. Do you understand?"

With our eyes still locked together, I nodded my head and told her I understood.

"Now, in just a few moments," she continued, "I'm going to sit down on the bed and look at you. I know this part is going to be difficult, but, I don't want you to cover yourself. Just stay still and let me look. Okay?"

My pulse was throbbing in my head, and all I could think about was how happy I was I didn't have a hard-on right then. It was embarrassing enough to have my mother look at me in a pair of panties. It was doubly embarrassing to have her see me with the frilly panties on. And when I thought about the prospect of her seeing me with a hard-on trying to poke its way through the pink, frilly material, I prayed to high heaven I wouldn't get hard in front of her.

She didn't wait for me to answer her question. She took a step backwards and sat on the side of her bed and pulled me right in front of her. Then, as if it was some kind of ceremony, she looked up at me, reminded me to be still and then her eyes immediately went to my crotch.

Looking down, I watched her face for signs of horror or disgust, but there were none. I saw her eyes flitter all over me down there, staring right at the puffed out bulge where my cock and balls were tightly nestled up against my body and then moving up toward my waist. Then, she leaned to one side, and then the other as if she was looking around my body at my butt.

Slowly, her hand came up and she carefully tucked her fingertip into the waistband of the panties and tugged at the waistband ever so slightly. A second later, she repeated the same thing under the elastic leg holes.

Without looking up at me, Mom told me she and my sister were shopping together the day my sister bought these panties. "I don't think she wore them very much." She said in a matter-of-fact kind of tone. "Too frilly for her, I think. But, they look wonderful on you."

"I think you probably wear one size bigger, though." Mom added as she looked up at me. "And these kind of panties are bikini cut, Jason. They are made to ride low on your hips."

"I'll venture a guess your sister's old panties don't hold you in very well when you get excited." Mom went on to say. "You'll probably be much happier with what they call the 'brief' style of panty. I've even seen some cute boyshorts that come up higher than a bikini, but still lower than granny panties."

Never in my eighteen years would I have ever thought I'd be having a conversation with my mother about the style of panties I should wear. In a strange way, it hit me as being humorous and I couldn't help but crack a small grin.

"If you'd let me," Mom said as she grinned back, "I'd be happy to take you shopping and we could find just the right size and styles for you."

"You know," Mom continued, "we could get you some everyday panties that you'd be comfortable in, and we might be able to find something more delicate for special occasions. Would you like that?"

Up to that point, I was able to stand there and let her look at me. But, as soon as she said she'd take me panty shopping, something in me snapped and I started getting these visions of her dragging me in and out of every store in the mall announcing at the top of her voice she was there to buy panties for her son. She brought me back to the present when she reached out with both her hands to hold mine, and when I blinked my eyes and looked down at her she said, "We can do it discretely if you're embarrassed about it. No one needs to know they're for you unless you want them to. Maybe I'll even buy some for myself. I bet it would be fun. What do you say?"

"Sure." I said, clearing my throat so I could talk. "I guess that would be good."

Mom smiled up at me and told me not to worry about shopping, adding that she'd take care of everything. I was starting to feel more comfortable now, especially since she'd offered to take me shopping and seemed to accept me wearing the ruffly panties. In a way, I got this feeling we were about done, and she was going to hand me my shorts and let me go to my room. But, I couldn't have been more wrong.

"Sweetheart," Mom said, as she looked up at me, "stay still for a couple of minutes longer. I'm just going to slip your panties down for a minute or two and have a look."

As soon as the words left her mouth, her hands rose to my hips, her fingertips pushed under the waistband of those frilly panties and before I knew what was happening, she had my panties part of the way pulled down. I watched in shock as she continued to pull, eventually pulling them down to the point where my cock and balls spilled out in front of her.

She paused for a moment, staring at my soft cock, and then slowly pulled the pink panties down to mid-thigh where she left them. Mom didn't say anything for several seconds, and when she finally spoke, I couldn't believe what she said.

"Sweetheart." Mother said as her eyes stared at my cock. "You're much bigger than I'd thought you'd be....... And bigger than your father was."

I guess it was supposed to be a compliment, and I guess I should have thanked her. But, with the way she'd been talking about taking me shopping for panties and then the way she pulled my panties down and was staring at my cock..... as much as I prayed it wouldn't happen...... it did. I started to get hard right in front of her.

She didn't immediately notice that my cock was hardening, but I could feel it starting to grow. And, just a few seconds later, she realized it herself. Her eyes popped open and she stared at my cock as it grew. She didn't look up at me or say a word, but instead, she stared at my rod as it lengthened and thickened right in front of her eyes.

Now, I'm not huge down there by any means. But, I think I have a decent sized hard-on once I'm completely hard, and it didn't take long for me to erect to the point where my cock was pointing at the ceiling. Looking down, I could tell Mom was totally taken by surprise, and I didn't know if that was because she was sickened and appalled that her son got an erection in front of her, or because she hadn't seen a hard cock since Dad died some fourteen years ago.

I finally had the good sense to move my hands over my cock and cover myself, but as soon as I did, she reached up and pulled my hands away and moved them to my sides and pressed them against my hips.

"It's nothing to be ashamed about, Sweetheart." Mom said with a shaky voice. "Don't worry about this. Just keep your hands at your sides and let me look."

I stood there, almost shaking, as my cock got harder and harder not more than two feet in front of my mother's face. It throbbed a few times and I heard her gasp when it shook and lurched.

"Oh, Jason," she moaned, "forgive me for saying this, but, you have a beautiful penis."

Then, realizing what she just said, she looked up at me and blushed. "I'm sorry." She said, almost whispering. "I shouldn't have said that."

Believe it or not, after another minute or so, my nervousness was completely gone. I stood there as she told me to, now proudly showing off my hard cock. In a way, I was filled with a sense of confidence, especially after hearing her say my cock was bigger than my Dad's and learning that she thought my cock was beautiful. So as she watched, I flexed my cock muscles and held them clenched, which caused the head of my tool to mushroom with blood and turn a deep crimson color.

"Does this happen a lot?" Mom asked. "These erections, I mean?"

"Well," I answered, "it definitely happens a lot more when I wear panties."

"And then you have to masturbate and they go away?" She asked.

"That's the fastest way." I replied. "But, they come back."

She raised her hands as if she was going to touch me, but she stopped herself midway and looked up at me.

"Can I...." Mom began. "I mean, would it be okay if I...... uh...... touched you?" She asked softly.

Looking down at her, I nodded my head to give my approval. She didn't know it, but, she would be the first female to ever touch my cock. And, as her soft hands gently wrapped around my shaft, I closed my eyes and sighed.

She touched me very hesitantly at first, almost as if she thought she was going to break the shaft of my cock. But after a few seconds, her grip around my shaft tightened and I moaned out loud. I used all my will power to send her brain waves begging for her to stroke me up and down, but, it didn't work. The only thing she did was rhythmically squeeze my shaft, alternating her tight grip and then a loose one.

"I can't believe how hard you are." Mom whispered. "Does it ever hurt?"

"Sometimes it doesn't go down by itself." I answered. "Then it might throb if I don't take care of it."

"By taking care of it, do you mean masturbate?" She asked, looking up at me.

I nodded my head and said, "Yes". Then chuckling a little, I told her that masturbation always seemed to work.

Another minute passed as she held my cock in her hands. Then, as slowly as she reached up to grasp me, she lowered her hands to her lap and looked up at me. All of a sudden, my mother's face turned dark red and she looked up at me. Softly, almost too soft for me to hear, she said, "It's okay if you need to do it."

A second later, she reached out to take hold of my hand and moved it to my straining cock. "Go ahead." She whispered, as she pressed my hand against my cock, "Show me how you do it."

It only took a second for me to realize she was asking me to jerk off in front of her. A million things started flying through my mind as she looked up at me, but it really sunk in what she was asking when she wrapped her tiny hand over mine and started moving it up and down.

"Don't be afraid, Sweetheart." She said. "Everyone masturbates. It's a totally natural thing to do. You go ahead and do what you need to do and I'll just be quiet and watch."

The last hour had brought about the start of a new relationship between Mom and me. I had totally confessed everything to her. She never raised her voice or reprimanded me for my behavior, and now, I was standing in front of her with my panties down around my knees, sporting a throbbing erection and she was urging me to masturbate in front of her.

I wish I could say I didn't want to do it, but, the fact of the matter is: I wanted to jerk off for her in the worst way. The hard-on jutting out from my crotch was evidence I was turned on, and at this point, I was filled with a new kind of excitement – the excitement that she was going to fully allow my panty needs, including my need to masturbate.

But it was more than that. Standing in front of her virtually naked with a hard cock was a new and exciting feeling, and the fact that she thought my cock looked good gave me a strange desire to let her look at it as much as she wanted to. I even considered how I might be able to get her to touch it again, maybe even jerk me off. And, the fact that she was my mother never entered into it at all. She had been a major focus point of my masturbation sessions for years, and it was more than just sniffing her panties.

I had fantasies of losing my virginity to her and having her teach me every facet of sex – even the really nasty stuff like anal sex. I had fantasies of touching her, her touching me and incredibly nasty things like her using me as her sex toy. All fantasies, that's for sure, but, things I thought about.

So, the fact that I was standing in front of her with my panties pulled down and a hard-on was right in line with my dreams and desires. I was enjoying being naked in front of my mother and the idea of letting her watch me stroke myself until I came was very enticing.

So, after a few moments of thought, I did exactly what she told me to do. I grasped my cock and started to stroke it. Slowly at first, I began to jack my cock, glancing at her from time to time to judge her reactions. When I first started, she sat there stoically and watched. But after a minute or so, she began looking up at me, meeting my eyes for an instant and then looking back at my cock.

I paused for a moment and held my throbbing member out to her, pointing my cock at my mother and then I squeezed it until a drop of precum appeared at the tip. When she saw it, she took a deep breath and looked back up at me.

"Sweetheart, do you think it would help if you had something to look at?" Mom asked.

"Absolutely." I replied, stroking my cock slowly.

She started to get up from where she was sitting on the bed and I took a step backwards without missing a stroke. Then, just like one of my fantasies, she pulled one arm out of her t-shirt and then the other, and pulled her shirt up over her head.

"I'm not eighteen anymore." She said, looking up at me as she reached behind her back for the clasp on her bra. "And, I've nursed two children, so don't expect my forty-two year old breasts to be young and perky."

The pace of my jacking had increased, and so had my breathing. Mom held the bra up to her chest after she unfastened the clasp, and then after a few seconds, she pulled her bra away and I saw her bare breasts. She dropped her hands to her sides and stood there, letting me look at her full boobs and large, pink nipples.

When I looked up at her face, I found that she was watching my fist fly up and down the length of my cock. I stopped my stroking and squeezed my shaft again, milking another drop of precum out the tip of my cock head.

"Is this helping?" She asked.

"Definitely." I answered. But I wanted more.

"Can I see your panties, too?" I asked.

"If I say 'Yes' would you do two things for me?" She answered.

"Of course." I replied. "What are they?"

"The first thing is," Mom began, "I'd like this to last a while, so promise me you won't finish until I tell you to."

"Well," I said. "I'll do the best I can. What's the second thing?"

"When we're done, would you mind terribly if I shaved you? Down there?" Mom answered, gesturing down at my cock. "Your father never would let me, and, I....."

"Sure." I replied, interrupting her. "No problem."

With that, I watched as my mother shrugged her shoulders and tucked her thumbs into the waistband of her sweat pants and pushed them down a few inches below her hips. Then, as she stared at my cock, she pushed her sweat pants down to her knees and looked up at me.

I'd seen her in her panties hundreds of times before, but, there was something different about seeing her this time. This time, it was purely sexual – and we both knew it. She was exposing herself to me in a sexual way, permitting me to see her panty covered sex. This wasn't the same kind of exposure that happened when she so innocently changed clothes in front of me. This was obvious. She was displaying herself knowing I was going to masturbate while I looked at her.

She stood that way for a full minute and then pushed her sweatpants the rest of the way down and stepped out of them. "How do you want me?" She asked.

I had no idea what she was asking, and she must have sensed this because after just a few seconds she said, "Do you want me to stand here, or lie down on the bed?"

"Lie down." I said. Then before I could stop myself, I added, "And spread your legs really wide so I can see"

Mom smiled. "Alright," she giggled, "but, you better remember your promise not to ejaculate until I say so. I want this to last a while, Sweetheart."

I watched as Mom sat down on the side of the bed and scooted back about two feet. Then, looking me straight in the eyes, she laid back, brought her knees up and then let them fall open. I was treated to a completely open view of her white panties pulled tightly across her pussy lips. And, amazingly, there was a dark, damp spot right between her legs.

My cock ached and throbbed, and as I moved up against the side of the bed, right between her legs ready to fulfill my end of the bargain, I wondered how hard I'd have to beg to be able to sniff her panties while she was wearing them.

To be continued.