a three part story, so make sure to read all of them!
I let Anna move in after she caught her husband cheating on her. She was devastated, of course. She didn’t leave him right away, though. She waited a few months, tried to make it work, and when she couldn’t, she left. She asked if she could stay with me, and I said yes.
I have known Anna pretty much our whole lives. We weren’t always great friends. She used to torment me, to be completely honest. But somewhere around 10th grade we started to click, and she’s been my friend ever since.
Of course, in stereotypical Hollywood fashion, I have been the guy who has lusted after her since back when she used to torment me. And after we became friends, I sat by while she dated loser after loser, patiently waiting for an opening. Anna rarely has openings, because guys flocked to her. She is smart and funny and gorgeous, and I am not the only one who fawns over her. Men do. Women do. Birds and stray cats follow her home.
But I missed my shot and landed in the friend hole. Which is fine. Anna is the type of girl who you’d rather have in your life than not at all.
And when she met Brian, I tried to talk her out of it. Not just because I wanted her, but he had that look. That lean and hungry look. I could tell that “forever” meant something else to him. All the guys before, all the guys I know, those of us who follow Anna around like we’re puppies, we look at her a certain way. We’re appreciative of her uniqueness. Brian never was. She was just another girl.
So, of course, she marries the asshole. She was 22. Too young. Anyway, two years later, she was at my front door, like a Hugh Grant movie, asking me if she could stay with me. Sure, I said. I only have one bed. But I can sleep on the couch.
Those first two weeks were horrible. She was heartbroken. Not so much about the cheating – I think she expected that; she was as naïve as I had thought – but about the finality of “forever.” She had bought into the vows, even if he never had. Her marriage was the first thing she had ever failed at, and it was crushing.
I was a good friend. I am a good friend. I gave her space when she needed it, gave her a shoulder when she asked. We’d watch TV at night, like an old married couple, her head between my arm, falling asleep. I’d look down and stare. Sometimes she’d wake up, and I’d pretend I was asleep, too. But I think she knew. Anna was observant.
I slept on the couch, even though she insisted she could. No, no. You need your space. It’s cool. My couch, though, is not the most comfortable, and Anna would notice I need to stretch more in the morning, that my normal aches and pains were more pronounced.
“Just sleep in the bed with me. We can share. Like when we were kids.”
“We never shared a bed when we were kids.”
“Yes. Of course. Remember that time at Tommy O’Malley’s lake house. Senior year? We got drunk and slept in the same bed.”
“No. You got drunk and slept in the bed with Richie Douglas. And Richie Douglas said he got to third base with you. I slept on the swing on the porch.”
“No. Richie. I never touched him! He tried to spoon me and I punched him in the stomach. I thought it was you.”
“You thought it was me who tried to spoon you and you punched in the stomach?”
“Then, no, I don’t want to sleep with you.”
“What if I inadvertently spoon you and you knee me in the balls?”
“Don’t be silly!”
“Look, we’re not 16 anymore. If you tried to spoon me … I’d let you. You know I like your arms.”
So I agreed. Even though I knew it would be hell. I knew it. I knew it. It’s like if you were addicted to heroin, and someone said that you could sleep in a bed of heroin as long as you didn’t inhale it. Really? May I lie down beside the thing I want more than anything else in the world but not actually know what it feels like. Thank you.
I made it through about a week, of just lying there, eyes open, for hours. Sleep would not come. She’d roll over, her body against mine. Or she’d fall asleep on my chest, just a thin pair of boxers and tank top separating her skin from mine. It was torture. Every cell in my body needed more.
I’d wake up in the mornings and beat off in the shower, first thing. I’d pump once or twice, tops, and that would be it. Done. Finished. A lifetime of relief washing down the drain.
I started jerking off before bed. I figured if I flushed it out of my system, I’d be fine. Wrong. It didn’t help. So I started jerking off before bed and in the AM, too. I’d have to jump up in the morning and run to the bathroom. I told her I had bladder issues. She probably thought it was like living with her grandpa.
Then, one night, I didn’t get a chance. A window. We fell asleep on the bed watching TV, and when I woke up, she was sound asleep. I didn’t want to wake her. I figured I’d ignore it. I’d ignore this throbbing erection, pounding away against the silk sheets. I’d ignore the way her hair smelled. The way she smiled when she slept. The way her brown hair fanned out beneath her, like she was a painting. I’d … fuck it. I had to cum.
So I jerked off in bed. I am not proud. It was desperate. But I needed relief. I sort of turned away from her and slowly stroked until I came in some tissues. She did not appear to stir. And I fell right asleep.
It was the beginning of another ritual. The thrill of almost getting caught – and the proximity of her body – made it doubly exciting. I was being bad, but I was rationalizing it as being good. This was my way of controlling the urges, not giving in to them. I told myself.
I got more and more bold. I stopped laying on my side, and would lay on my back instead. Her face just a few feet away. I’d jerk my cock until I came on my chest. Sometimes letting it dry as I slept. She never moved.
Friday night was the worst. She had a date. Her first since the separation. She looked like a vision, in a small dress and her hair up. Luckily the guy was a dud, so she was home early. We ate ice cream, watched TV and went to bed. But the agony of seeing her like that, and the pain of knowing there were yet another long line of guys who I’d have to wait for, was too much.
I jerked my cock with more force. Angry. Sad. Jealous. I wanted to cum, and I wanted it to feel good, but I wanted it to hurt. I wanted it to be intense.
“Are you OK?” she said.
“Shit,” I muttered, sort of turning. Her hand was on my back. “Sorry. Uh, dream.”
“Don’t be silly. I know what you were doing.”
“What? Huh. No. Uh. Nah.”
“You’ve been doing it for a week or two. I know. Most nights I just watch. I didn’t want to bother you. I just laid here and pretended to be asleep. I am sorry. I figured it was my fault … putting you in this position. Lying here. I am not a little girl. I know how guys are. I know it has to be hard, um, I mean, you know difficult.”
I was embarrassed but turned on. How did she see me? Some horny teenager or a man. I rolled over, on my back, unable to look at her. I stared up at the ceiling. She nuzzled her head onto my shoulder, but I just sat there, hands behind my head.
“Talk to me.”
“This is weird,” I said.
“No. It’s not. Seriously. I liked watching you. Trust me. I … have been going through a lot of stuff. Self esteem stuff. I liked knowing I could do that to a man. I should thank you. Thank you.”
“Ha, you are welcome.”
“And I wouldn’t have said anything, but you just seemed … different. Angry. I didn’t like it.”
“Sorry. It’s just … long day.”
“I know,” she said. “I get it. Trust me.”
Her hand was on my chest, just resting there. We sat in silence. I wasn’t sure what to do or what this meant. Clearly, making a move was not my strong suit. Which is why I never made one.
Then I felt her hand slowly move south, beneath the cover, over my stomach. My cock was still stiff. I was trying to ignore it. But her hand on my stomach made it jump.
“You didn’t finish,” she said.
I felt her nails in my pubic hair, trailing around with light scratches. Then I felt her hand grip the base of my cock, her fingers tightening around the shaft, pumping up, over the head, then back down.
“Is this the way you do it?” she asked.
“Yes,” I said, my head spinning.
Her hand jerked me again, faster, up and down, over the head and back down. She turned and kissed my chest lightly as she jacked me, kissing one nipple, then the other as her hand worked up and down my shaft. She’d pause and her fingers trail over my head before falling back down, hard.
I exhaled as she kissed my nipple, teasing me with her tongue. She was so gentle, but knew how to handle my cock. I pulled my hands up, rubbing them over my face.
Then she paused. A quick pause. Just long enough to grab her tank top, hoist over her head, throw it across the room, then back down.
Her hand kept jerking my cock as she licked my chest, looking up at me. I could feel her hard nipples on my thigh as she trailed down. She continued looking at me as she hovered over my cock, kissing it lightly as she jacked it.
Then her mouth was on me, over the head, licking my precum. She trailed her hand down, to my base, then back up, her tongue licking the underside of my shaft.
Her left hand reached up, clawing at my chest, teasing my nipples. Her brown hair was fanned out around me, over my legs, shielding her face and framing it. She was … breathtaking.
All of this took about two minutes. I’d like to pretend she blew me for 30 minutes. But I couldn’t last. Not with her. Not with how good she was. Not with being so close before.
She jerked my cock, milking me, getting me close. I tensed, lifting my hips and giving her the tap. “I’m going to cum,” I managed to say, expecting her to pull away. No. She sucked harder, jerking me with her hand. Fuck. Christ.
I came hard. The room spun as I unloaded in her. She jacked my shaft the whole time, squeezing every ounce out. She was loving and giving, wanting to make sure I was completely satisfied. I melted as I came.
“That was a lot,” she said, smiling.
“Yeah,” I said. “Backed up.”
“I bet. What, 10 years worth?”
“Ha. Yeah. Something like that.”
She moved back into my shoulder. Her shirt off, I could feel her warm skin against mine.
“I could, you know, I mean, I am sorry you didn’t. I could …”
“Not tonight,” she said. “I am tired. Maybe tomorrow. I mean, we’re sharing a bed. There’s no reason we can’t … be there for each other.”