Hey, guys. What’s up. So I heard that a few of you guys liked my story. Wanted to know if I’d ever seen that girl again, or perhaps did a little more than just see her … Well, I can tell you that taking her virginity was only one of the several firsts that girl had with me. The next one came about ten days later.
I had texted her out of the blue, wanting to test the waters. I hadn’t really heard from her after we did it, and I wanted to make sure she felt okay about it. Turned out she was more than okay. And wanted to do it again. Truth be told, so did I. So we worked out a little arrangement.
Her parents were kind of loaded, and they were able to set her up in a hotel room for a week for a sort of staycation. Apparently she’d been doing that since she was a kid, and was allowed to bring a friend. I don’t know for certain, but I’m pretty sure they didn’t know what we were planning …
When I arrived and we met up, she was so excited and nervous and jittery she could hardly speak in straight sentences. I told you this girl was fucking adorable.
I asked her what she wanted to do, if she liked what we did or wanted to try some other stuff. She didn’t know. I could tell she was so fucking thrilled and terrified just to be there with me again, but was so inexperienced she didn’t know what to ask for, let alone what she liked. But I didn’t mind. I was starting to really like this girl and was more than happy to figure this out with her.
I asked her a few matter-of-fact questions, just basic stuff, but you could tell she wasn’t used to talking about this sort of thing at all, in normal conversation or otherwise. Her eyes got big and serious and she muttered a few indirect responses, but after a few minutes of probing I started to get the idea that she was pretty sure she liked penetration … more than clitoral stimulation. Which is unusual but not unheard of. Turned out I had actually guessed right the first time when we did it and I’d slipped a finger in … but a finger may not have been enough anymore.
I asked her if she’d ever heard of strap-ons. She got all nervous and muttery again but basically told me in broken sentences that she’d heard of them from a book on sex her parents had gotten her when she was fourteen, but hadn’t really thought they were mainstream or anything.
Was she about to be surprised.
I told her to wait there.
She went quiet, still shy and nervous, but now a tiny and intense and slightly embarrassed smile was spreading across her face and her cheeks were getting pink. I didn’t tell her what I had in mind, but I guess I didn’t have to. She could probably guess where my mind was going, and when I showed up a few minutes later in full harness and dildo, she drew in a breath and looked away modestly, bashful but not surprised. Clearly she’d never seen one in real life before – in the flesh, so to speak – and wasn’t prepared, even if she half-knew to expect it.
I’d anticipated this sort of thing too, and with my luggage had brought a full-ass duffle bag with assorted toys and other stuff I thought we might want to use to spice things up a little.
I had picked out the smallest and most harmless-looking one I had – fucking *purple*, no less – but we still had to go slow. Like, *glacier* slow. I didn’t mind. I was right when I’d guessed she’d never been penetrated by anything before, let alone a fucking dildo, and I knew how much the initial stretch can sting.
Let’s just say, firsts are not always ‘hot’ or ‘amazing’ but sometimes more mechanical, tentative, or academic, and that’s fine. Sometimes the fire and the magic come after, on the second time or even later, and it was like that with her.
But I still wanted to make it as easy on her as I could.
We got comfortable on the bed and I took it from there. I started making out with her again, this time taking my time and adding in some touching and caressing.
I ran my hand up the side of her neck and entwined her hair with my fingers, gripping a little. Not too tight, but I heard her gasp and felt her pulse quicken under my touch. I could feel her fingers curling around the tops of my shoulders, gripping my shirt tighter and tighter … then going limp and falling away. She was fucking melting again, just like the last time, except now I was stretching it out, with no hurry. We had nowhere else to be.
I wound a hand around her waist, tangled my fingers in her shirt, worked my way up higher, gently cupped a breast in my palm.
She ran her hands up my chest, the sides of my face, into my hair … still helpless and reaching but gaining fervour bit by bit.
We continued like this, me taking the lead, gauging my movements with her reactions, until I thought she was ready.
I reached down and undid the top button of her pants, slid my hand down. She was totally unshaven, and I let my fingers play for a minute in her hair before going further down. By then she was damp, but not quite as wet as I needed her to be for what we’d be doing.
I slid my index and middle fingers inside her and caressed her clit with my thumb and heel of my hand.
Once again she sucked in her breath in a gasp and her eyes rolled back and slid closed and her head fell onto the pillow.
I smiled, pleased. I was getting her really into this, but I knew that this time it was just the opening act. The main attraction was still coming, and it may not be as awesome.
But in the end it would hopefully be *more* awesome, at least if I could help it.
That’s why I was really taking my time with this – I wanted it to be as nice for her as possible.
Because once she was warmed up a little and we’d gotten her pants and underwear off, it was a process of two steps forward, one step back.
I got her to take control of the dildo, hold it in her hand so she could go at her pace. I kneeled above her and braced myself on either side of her head, but let her be the one to move it in and out, or in her case, a tiny bit in … hold for a second … then back out … a tiny bit further in … then back out.
Each time she shut her eyes in concentration, furrowing them or hissing through her teeth or even chanting *‘ow-ow-ow-ow-ow’* under her breath when the pain got too much.
Eventually she managed to get the full thing all the way in, and that’s when we could really start having fun …
But I’ll save that for Part 2 …
Hey, guys. Thanks for coming back for my stories. I had to break this one up because it was so long, but I promise not to keep you waiting too long for the rest of it.
And there’s more stories to come. Like I said, she spent the whole week with me, and this wasn’t even the hottest time I had with her, so if you’re interested in hearing about how we threw a few kinks into our play, be sure to keep an eye out for it.
In the meantime, if you have any comments or questions, feel free to hit me up with a private message. I don’t have much patience for guys just trying to be gross, but like I said in my first story, if there are any virgins out there who want to know more, I’m always down to make time for you and help you out.
Until next time …
-Gwenn
Source: reddit.com/r/sexystories/comments/n1kc47/i_f21_introduced_my_friend_f19_to_strapons_long
What a beauty.