Christine’s First Time(s) – Part 1 [MF, Chubby, “Virgin”, Non-Fiction]

We found each other on Kink.com or some similar fetish style website, way before online dating and other things were the norm.

Her profile said she was 20, into tons of things but what caught my eye was that she was submissive, had an oral fetish, and seemed to attend the college that I lived down the street from.

She turned out to be real, and who she said she was. We exchanged progressively dirtier emails, and eventually talked on the phone. It felt like I won a weird sex lottery by finding her literally out of nowhere.

*

Turned out she was living in another town, away on a coop term. But when she was visiting town for a weekend we made plans to meet up for coffee.

She seemed nervous even in the planning.

When I met her a few things jumped out.

First, she was much heavier than the pics she’d shown me. I couldn’t really tell, but if I had to guess, maybe 30-40 pounds more. It was the same girl from the photos for sure, but, probably a year or two in the past. I wasn’t upset, I like a woman with a bit of meat on her bones. She was maybe starting to approach the limits of that, but I still found her sexy. Nice huge tits, a nice round ass, and what attracted me was the extra bit of pout it put in her lips.

But I could tell, she was super nervous. And that was the other, more important, thing that jumped out – any confidence she had on the phone or in emails seemed to be gone.

She started by apologizing almost the second she sat down.

I don’t remember what she said but I remember being impressed by how she “fell on the sword” right away, admitting she had mislead me, and I honestly hoped she’s fall on my sword not long after.

I smiled to set her at ease, told her honestly that I liked a curvy girl and it was okay, but she was crazy nervous anyhow and it didn’t seem like my words were getting through to her.

Then it struck me what to do.

She claimed up and down through her profile, and in our various emails and chats that she wanted to be dominated/that she loved to be submissive.

I reached across the table, grabbed both her hands firmly from where they sat fidgeting in front of her, I looked her in the eyes and said slowly, “Calm down. I’m glad you’re here. I want to be here.”

That at least got her to stop talking and take a breath.

I told her I was going to get us each a drink and she needed to calm down. That when I got back we would start again.

*

She still seemed amazingly nervous, but at least, a bit more at ease. Enough we could have a conversation.

After what was friendly chatter for quite a while, she hit a dead pause in the middle of a sentence, she looked at me and said, “I shouldn’t have come.”

I knew there were two ways it could go from there.

I honestly did like the girl on a human level and we’d had fun in our chats, and I was attracted to her even if she wasn’t as advertised. I felt like, given what we’d discussed, if she was actually willing and interested we could have a lot of fun. But at the same time I didn’t want to push her.

What was obvious to me was she had nowhere near the experience she made it seem like she did when we talked. I wondered if this was her first ‘date’, even though I wasn’t sure if that’s what you should label it when you are clearly meeting as a prelude to sex.

*

I stared at her for a long time. She didn’t say another word, and her eyes were asking me to say the next ones.

Finally I said, without breaking eye contact, “Christine, that’s up to you really. I really do like what I see. Those things we talked about doing, I really do want to do with, and to, you. But it’s your choice if I do…”

She finally smiled at this. I could see it, that kinda smile you try to hide. Really, I was delighted but I felt like part of my role was not to really call that out. I was to be demanding, that was part of this, and part of the lure at least for me.

Since she seemed receptive, I thought quickly about my options… and decided pushing her a bit wasn’t a terrible thing.

“So here is the deal Christine. You can do one of three things… do you remember the first story I told you, about the girl with the blue ribbon in her hair?”

She nodded. I could tell she remembered, and if I remember right, it had something to do with a girl putting the bow in her hair as a signal, that the guy she was meeting should eat her pussy on sight, without saying a word to her. I think I could actually see her squirming.

“Well, option one is you meet me here again tomorrow – I know you’re still in town – you go home now, you think about what you’re up for, and I’ll be here tomorrow either way. If you meet me here wearing a blue bow, I’ll take you back to my house on sight without you saying a word, and we’ll start living out some of those fantasies we’ve talked about… or you could just show up without the bow for another coffee and we’ll make friendly if that’s all you’re looking for.”

She turned a bright red, but she didn’t break eye contact. I could tell she wanted to be the girl from those stories and fantasies. I was starting to enjoy the control I could tell was extending over her already.

She didn’t say anything so I continued, “Option two, is you just walk out of here and never come back. And that’ll be okay, but know it’s not what I am hoping you are going to do.”

Then I said, “Or three, you come over and sit beside me in booth, and I’ll prove to you I really do like the body I see.”

*

She didn’t say anything. She smiled. I watched her intently, it looked like she was trying to say something a few times, but all of those were false starts.

She drank her coffee and stared at me the entire time. And I did the same.

It was a weird silence, not uncomfortable, more, calculating.

And honestly, I was starting to get a bit hard at the possibilities. She hadn’t run away screaming. I was proud of the options I’d been able to dream up on the spot. If anything I did hope I was giving her a bit of confidence, I hoped that was building in her.

*

She seemed to drink her coffee forever. Holding the mug between her two hands, elbows on the table, looking at me over it, almost not daring to look away.

Finally, she sat the cup down, closed her eyes and I imagine made her decision.

She smiled, opened her eyes and stood up.

I assumed it was to say goodbye. I was a bit disappointed, but it had been an interesting way to spend an hour anyhow.

I stood up too and figured I would hug her goodbye if her nervousness would allow it, or at least shake her hand.

She stepped toward me and I went in for the hug, I did it genuinely.

I whispered in her ear, “I really am glad you came.”

She shivered in my embrace.

Finally she whispered back, so quietly I almost couldn’t hear it, “I really want option 3.”

*

I sat her next to me, between me and the wall. I just motioned, and she obeyed, and I hoped that would be a trend.

She sat there and my leg was pressed against hers, and I could feel it trembling.

I whispered in her ear, “I see you wore a skirt, like I asked you to.”

And I let my hand drop down below the table top, and I rested it on her thigh, the inside of her thigh, low, near the knee. Just a first touch, as far away from the prize as I felt I cold start.

I could feel and hear her gasp.

I ran my fingers gently up and down her inner thigh, over the flesh of her leg, letting it naturally hike up her skirt.

I could feel the rhythm of her breathing, it was as if I was playing her like an instrument. She’d exhale as my fingers and palm got further from her pussy, as they made toward her she’d hold her breath.

I whispered, “Did you wear panties or not?”

And I let my fingers finally climb all the way up, and I felt the material of what she was wearing.

I could hear her muffling small moans as I started rubbing the bottom of my hand gently against the material. Just sort of, massaging the pussy underneath it gently. And I could feel her squriming back against my hand. Her pussy was hungry for my touch.

*

I whispered, “Bad girl Christine, wearing panties when I told you not to… maybe I should stop.”

And with that I did, I just left my hand there, my fingers and thumb clutching her thigh, my hand pressed against the wetness of her panties, but I didn’t move it.

I felt her trying to grind herself against my hand. Which was nice, but I wasn’t going to let her. I pulled my hand away now and put it in my own lap.

She made a whimpering sound.

I revelled in these little pleasures.

*

I reached across with my outside hand, and put it to her cheek gently, and turned her face toward me. I turned my body toward her. I started to bring my lips toward her’s and she closed her eyes expecting a kiss. But I instead brought my mouth toward her ear, putting us cheek to cheek, and I could feel her lips puckering beside me in unmet anticipation.

I whispered into her ear again, directly this time, “Was this the first time anyone has touched your pussy…”

I was bold now, I let that hand that had been holding her face escape down to her pussy below the table, I reached between her legs, where her skirt had been hiked up, I worked my fingers fast into the front of her panties, pushing the tips between the elastic and her flesh, push them down over her hood, curled them up into her opening so just the tips flexed a bit inside.

She was soaked. And as a result, my fingers were soaked almost instantly.

I don’t know if she was aware of all the people who surrounded us and maybe could have saw. But I was, and wanted to be quick, even if I was daring, so I risked maybe 5 seconds of fingering, probably not even that. But God I felt like it was enough she might have cum just from that alone if I’d let it go any longer.

I pulled my fingers out of her panties, and returned my hand to where it had been on the side of her face, then pulled my own head back so I could look her in the eyes.

I let my finger tips trace along her cheek, and found her lips with them.

I just gently traced one of the fingers over her sexy little pouty lips, and I swear to god she was fighting back to urge to suck on it.

She tasted herself before I ever would, and that was how I honestly loved it.

I was enjoying innocent little Christine.

I pushed my finger between her lips now, just a bit, just the tip inside it, as the tip had been in her pussy under the table seconds before.

I felt her suck on it, just gently, but I knew what she wanted it. Her eyes were still closed.

I felt my cock straining against my jeans now, and I imagined how she’d look worshiping my cock with those lips. I knew at that point, it really wouldn’t be long before that would be happening, and judging by our very abbreviated encounter, I knew it wouldn’t take much to turn her into whatever I wanted. And I knew I’d enjoy doing it.

I pulled my finger away, and grabbed a napkin off the table and made a show of wiping my fingers clean as I smiled at her with my best impersonation of the devil.

She opened her eyes just in time to catch it all. And the timing had been perfect. In fact, the timing of everything had been perfect.

I said, “So Christine, nod if you believe me that I can’t wait to enjoy your body.”

She did, and it may have been the first act all night she did without hesitation, but, with the same stupid grin on her face.

And I said, “So tomorrow, right here, at the same time…”

I patted her on the thigh as I stood.

I smiled as I looked back down at her one last time, “If you wear a blue bow, I’ll take you home and teach you how to suck my dick… and if you wear panties like you aren’t supposed to, I’ll make it rough. Nod if you understand.”

And she nodded with enthusiasm.

Source: reddit.com/r/eroticliterature/comments/fttgf8/christines_first_times_part_1_mf_chubby_virgin