My wife was friends with a real wild child when we were in our early 20s. We'd gotten married early and were her "stable" friends in a crowd of ne'er-do-wells. She was one of those "smoldering" types I immediately had an attraction to. There's some people who are like that; where you know you'd just click sexually. Maybe it was because her relationship was on the rocks and she was likely not getting any. She always seemed a bit "pent up". Occasionally, I'd overhear conversations between her and my wife where she flat out stated that she needed a hammering. These little eavesdropping moments always gave me a thrill.
She was raising twins as a single parent after an on-again-off-again relationship with their father. Ultimately, she knew he was no good for her and so left him one night, and to our house she came.
My wife, the caring friend, was up in the other room with her once her son had been put to sleep, and I was in the den binge watching some series my wife wasn't into. I heard the wailing and crying and anguish of a lonely single mother in the other room and my wife doing the consoling.
A minute later, in my wife comes to the den on a mission, pulling her friend behind her. She was looking very sad and dejected, indeed but also a little sexy in her button-up sleep shirt and boxer short pajamas.
I paused the show I was watching.
"Babe," my wife sounded as if I was in trouble. Had I been caught giving her friend a once-over..?
"Uh, yeah...?"
"Mandy needs to be held," she said.
I was confused. "Held? What do you mean?"
"She needs to be held in the safe arms of a strong man."
"Okay?" I felt like this could go nice and wrong really quick, but my wife dragged her in by the hand all the same. "What do I do?" I asked.
This was so ridiculously awkward. There's this woman who I'd be in bed with in an instant looking like a sad, lost puppy being thrust literally into my very confused embrace.
"Just lean up against the arm of the couch, let her sit in between your legs with her back to your chest, wrap your arms around her, and hold her. She'll just sit quietly and watch your show, or she might sleep. She's exhausted."
"....right."
I pulled back the blanket I was using and got in position like a good boy would. I was only wearing some pajama pants and a t-shirt. She crawled onto the couch and assumed her position. I covered her attentively with the blanket, and wrapped my arms around her.
Leaving the room, my wife turned the lights off. "I'm going to bed. I'm tired."
Granted, it was past the time my wife would usually head to bed. She sounded a bit irritated, and I imagined that this friend of hers was being given to me to "look after" since I was going to be up for a while, anyway. Kind of a, "Tag! You're it!" scenario.
We stayed in silence for some time. I figured it was better to just remain quiet than try to talk. Plus, I'd been told I didn't have to talk. All I had to do was hold her. Sounded easy enough. So I did. I thought maybe she'd drift off.
I tried to pay attention to the TV show, but occasionally, she'd kind of sniffle and snuggle into me. So, I'd wrap my arms a little tighter around her. My arms were around her waist, with my hands near her belly button. Her arms were over mine, kind of holding my hands. Her shirt had ridden up a touch and I could feel the smoothness of her stomach under a few of my fingers, and I liked it.
She was a little curvier than my wife, in the physical sense. She just had more meat on her, which I didn't mind. A nice thick ass, slightly bigger boobs, a bit of a belly... that nice 'romantic era' body you see in paintings. Short, brown hair to her neck, a really nice smile and sparkly eyes. Really, I couldn't fault her anywhere physically.
When I was examining her upon her arrival in the room, I could tell she wasn't wearing a bra, and from what I knew about her and what my wife had told me, she wasn't really "into" underwear. My wife considered her just a laugh-a-minute oddity and I'd been informed about all this very matter-of-factly in the past. But now, with this woman in my arms and my wife having gone to bed these details came curiously back to me.
Now, this might make me a jerk but what started out as me hoping she'd drift off, now became my plan to pretend to drift off myself. I figured that if I wasted the opportunity to "snuggle in" in my sleep, and maybe even move my hands where they might not have gone when I was awake, I'd kick myself. I'd do so very innocently of course, testing the waters, positive that if I put them anywhere she was very uncomfortable with, she'd either move them, or hop up and go to bed, in which case I'd have been "asleep" and therefore blameless, and all would just go back to the way it was.
First, I knew I had to get us in the right position. Feigning slight discomfort I whispered to her, "Can we slide down a bit?" So we wiggled our way down the couch and I put some pillows behind me so that I could rest my torso and head fully on something, and so that she could rest of her head on my upper chest, or even snuggle her face into the crook of my neck, which she did, apparently having no interest in what I was watching. I turned the TV down just a little to put us into the "sleeping mood". Her face was turned into my neck and I could feel her softly breathing in and out of her nose, which sent a shiver of excitement up my spine.
I repositioned my hands a little further up her belly, resting just below her breasts, intentionally but innocuously dragging the bottom of her shirt up with them. I intentionally didn't touch them, because though I'd whispered to her sleepily, I was still obviously awake. I didn't want her suspecting anything at this point.
We rested like that for what I felt was a long time, but was probably only 5-10 minutes. I was trying to lie as still as possible. I wanted her completely relaxed.
Then, I started intentionally "twitching" my hands, like people sometimes do when they're in the latter stages of falling asleep. I did this a couple times, and she actually comforted me by resting her hands on mine and caressing them. With my hands resting just below her breasts, and her hands resting on mine, we just lay there like that cuddling for a while. I let the twitching thing go, as if I'd fallen into deep sleep. She sighed like she was totally, blissfully happy and relaxed... and then I made my move.
I "repositioned" in my sleep.
You know... when you move around in your sleep. Go from your side to your back. Or your belly to your side. You just reposition.
My arms were under hers, and with my whole body, I wriggled a little bit, but obviously she was lying on me, so I couldn't move. This was intentional. I wanted her thinking I'd tried to just get comfier and ultimately be unable to. The only thing that really had any freedom were my arms and hands, so I crossed them over her chest, and effectively cupped her left breast with my right hand, and her right breast with my left hand, and then squeezed her like I was giving the biggest, breastiest teddy bear a cuddle in my sleep. I knew I had to just go for it because I was really only going to get one chance.
I waited for her to move off me, go to her room, take my hands off her, scream out "RAPE!" or "PERVERT!"... whatever. But, she didn't.
Instead, I feel her gasp, like I'd taken her off guard, to begin with. Then, after a minute of nothing but breathing, I feel her doing something with her hands, but I honestly can't figure out what it is. She's... fidgeting or something. Playing with the bottom of her shirt, maybe? It feels like she's messing with her shirt.
Given that I've got two hands full of boobs, I'm just content to lay there and let her do whatever. I'd sleep there all night if she let me. But, then I feel her hands making their way up her torso, and I know what she's doing...
She's unbuttoning her sleep shirt.
