Sissy Biography - X

Fast-forward a few years and I met a lady named Paige…again…sorta…

What I mean is I had seen Paige around the office for a few years, and had exchanged pleasantries with her on more than one occasion, but had never really taken the time to get to know her.  Paige was strong-willed, smart, and sarcastic without being mean spirited.  She had dark brown hair, and green eyes that contrasted her porcelain skin.  In short, she was awesome, and she was beautiful.

We never really engaged with each other outside of work because she was married with kids, and I was in a long-term relationship at the time.  Somehow, the stars aligned and we were put on a project together just a few months after both of our relationships ended.

We hit it off like goddamn gangbusters.  We were into the same kind of stuff (classic rock and goofy horror movies), we both loved the same kind of bars (as seedy as you can get without being mugged), and neither of us were looking for anything long-term due to the recently deceased relationships.

 

It didn’t take long for us to start meeting outside of work.  It didn’t take long for that to progress to something else.

The sex started off great.  Passionate.  Heated.  You know, the way sex is in the early days of any relationship.  The only real problem is that it was pretty infrequent because we had to schedule around her kids.  She didn’t want them to think she was already shopping for a “new daddy” and I sure as hell wasn’t ready to have kids in the mix.  When the project ended, our lives went perpendicular to each other’s for a while, leaving me a little frustrated.  I think I’ve said this before, but when I get frustrated, I tend to start going further out with my…stuff.

In short, I may have signed-up for an online sissy-training on Akashaweb.  For those of you who don’t know, Ms. Akasha was an online mistress who was active from 1995 until about 2016 when she decided to go her separate way from the online training biz.  If you’re on her mailing list, you can still get offers to participate, and the trainings are fucking amazing.  She’s a master (mistress) of teasing and denial, and humiliation both public and private.  Just thinking about it is getting me fucking wired. 

Anyways, Ms. Akasha’s training was about a month long, and it only became stricter and more depraved as it went along.  I was in week two and currently under orders to remain in chastity and to wear a specially bought pair of panties at all times.  I wasn't wearing a cage, but I was forbidden to touch myself.  That’s when I got a text from Paige: 

Hey, hot pants!  I haven’t seen you for a while!  I’ve got some free time this week, if you want to get together for some dinner.  Just let me know! ;)

For some reason in my weird sissy-brain, it didn’t occur to me that I would be hearing from her during my training, let alone an invite to dinner.  I was in the middle of a sissy-training and I really wanted to finish it off right, but I also wanted to see Paige.  I responded the only way I knew how: 

Sounds great!  Just give me a where and when!

We met up for dinner that week; dim lights, bottle of wine, a nice time.  We talked about work, and about how we needed to pressure our boss to get us to work on another project together.  It was like no time had passed between us.  Underneath it all, I was wearing a pair of lacy, red bikini panties.  Every time I shifted in my seat, I was reminded of what I was…of what I was wearing…of who I belonged to…

It didn’t seem to be much of a problem, until, towards the end of the meal, Paige gave me a smokey look and said, “You know, my ex has the kids.”

An erection immediately began to strain into my panties, and I swear I felt my pupils dilate.  I hadn’t had any kind of release for two weeks, not even a ruined orgasm.  There was nothing more that I wanted to do than take this beautiful woman home and fuck her like there was no tomorrow.

I sitting in a dimly lit, romantic restaurant, directly across from a beautiful woman who was actively telling me that she wanted to take me home and have sex, and all I could do was sit in my panties and refuse her offer.  I almost came in my pants at the thought; I belonged to someone else and would probably be outed as a sissy if I betrayed that (how would I hide my panties if we went to have sex?).  Hell, I was probably going to be outed as a sissy anyways, when I refused.  She wasn’t the type to take polite refusal silently.

She looked confused when I didn’t answer right away, “All right, so what’s going on?”

Like I said, she wouldn’t take it silently.  Especially given the fact that our relationship had two ground rules:

1. Nothing long-term.
2. Complete honesty, even if it hurts to hear.

I leaned in close and told her.

I had previously hinted that I get into “some weird stuff” when left to my own devices for too long, but this was the first time I ever got into specifics.  I let her know that I was doing an online training that included humiliation, I told her that I wasn’t allowed to cum, I told her that I was only allowed to wear panties.

“Are you wearing them, now?” She asked.

“What?”

“Are you wearing panties, now?”

I felt myself flush, and a devilish smile crossed her face.

“Show me,” She said, her voice halfway between a dare and a command.

“What?”

“I want to see.”

I took a quick glance around, lifted my shirt, and raised my lacy, red waistband over my belt, lifting myself off the chair far enough for her to see.

“Oh, my god!  That’s great!” She said, a little too loudly, giggling into the back of her chair, covering her mouth with one hand.

I felt myself flush again, feeling like the entire room had their eyes on us.  Of course, I was completely erect by this point, and probably staining my panties in pre-cum.

“So, wait, you aren’t allowed to have sex?” She asked.

“Not really, no.”

“Any kind of sex?”

I felt a warm pulse go through me.

“Well, um…what do you have in mind?”

She smiled, “You’ll find out.”

We paid the check, drove to her place, and made a beeline for the bedroom.  She laid back on the bed, and gave me a flirty look, like she was expecting something of me.  Finally, she spoke:

“Take it off.”

I slid off my shoes and socks, then my jacket.  I unbuttoned my shirt and dropped my pants, exposing my panties…also, my rock-hard erection...and a pre-cum stain on the front.

She started giggling, again, “God, you weren’t joking!  You really get off on this!”

She waved me over to her—she, while still fully dressed, embraced me, wearing only my panties, and kissed me deep and hard, running her hand over the front of my panties.

"Not tucked?" She asked.

I only groaned.

We made-out like teenagers, never parting lips, our hands roving over each other’s bodies, hers occasionally rubbing lightly over my panty-covered cock, causing a sex-fueled gasp to emit from my lips each time, and causing her to smile each time.

Eventually, she pushed me back, peeled down her panties, and guided my head in-between her legs.  I went to work with abandon, my poor neglected erection throbbing against its lace-fabric cage.  She breathed deep, and she breathed long, grinding against my face, as she built closer and closer to climax.

Suddenly, she pushed my head back and reached into her nightstand, producing a vibrator, shoving it into my hand.

“Fuck me!” She said.

I obeyed, penetrating her hard and deep, using my now-free mouth to pay attention to her clitoris.  She didn’t take long, her body tensing harder and harder as she pinched her nipples and bit her lip, moaning deep and long, until she gave a throaty groan as her body arched off of the bed, ultimately collapsing onto now sweat-covered sheets.

I withdrew the vibrator, and crawled over to her.

“Fuck,” she said breathlessly, “I needed that.”

She pulled me down for a post-orgasmic kiss and reached between my legs, rubbing a cock-head that had become drenched with pre-cum.  I shuddered.

“Are you sure I can’t do anything for you?” She asked,

“I’m sure.”

She gave a pouty groan of disappointment.

“That’s fine, panty-boy,” she taunted, “I got what I needed.”

I chuckled, and lay down beside her.  Within minutes the two of us were asleep.

We woke up early, because she had to pick up her kids.  She giggled when I went to put on my pants.

“God, you're so weird.  I mean, really, panties?”

“It didn’t seem to bother you too much, last night,” I quipped.

She smirked, and tilted her head, “I guess not.  But, I think we need to have a talk about all this.”

“What do you mean?” I asked, feeling myself wilt a little inside.

“Well, there’s some things I always wanted to try out, but I couldn’t get my ex onboard.  If you’re game for some stuff, I’m game for…” she pointed at my panties, “whatever this is.”

My erection returned pretty quickly, and I lost the ability to really think coherently, “Uhhh, yeah, no, of course.  I’m definitely up for a talk.”

She giggled at my confused enthusiasm, “All right, then.  We’ll talk soon, hot pants.”

Sad to say, that talk never happened.  It’d be about a month before I saw her again, and by that time she had garnered herself a new boyfriend—a new boyfriend who was supremely jealous of me.  While he didn’t know how far the two of us had gone, he knew that we were close, and that bothered him.  Shame.  If he hadn’t been so resentful, who knows what kind of mischief the three of us could have gotten up to?