Red Red Wine

Buildup: Vacation time — I had been in a non-stop low-level state of arousal since the magnificent sex of the landing strip revelation and the usual allure of vacation beds. B not so much — the bed at this place was not so comfy, and in any case she was looking forward to catching up on sleep. As a result, the first two nights passed with no nookie. On the third night of vacation, I got a little anxious and impatient, drinking a glass or two of red wine to get in the mood, and another glass or two after B turned in for the night.

Foreplay: I stumbled to bed — TDTF, but determined to try. B was already asleep, and when I began pawing at her, she was “antsy“. The tried and true method of arousal is to put her hand on my crotch, and she squeezed my hard shaft until she was ready to feel it inside her.

Main Event: Straight missionary — B wasn’t very responsive. I began pumping just to get off, and the combination of the wine and oncoming guilt for waking B when neither of us were that into it caused my hard-on to get progressively squishier. It was at that moment that B started moving her hips and rising against me — that made me come in a semi-soft state and left her high and dry (or high and wet.)

Afterplay & Afterglow: None. Back to sleep for B — me lying awake in the dark, knowing this would be a dreaded 1-star entry.

Rating: ★

Routine

Buildup: Not much really, other than a lingering what-could-have-been memory from the hottest parts of the night before, and my guilt that B didn’t get to come that time.

Foreplay: B slept facing away from me in a tight tank top (sexy, but hard to get my hands under to play with her breasts) and a pair of pink-striped cotton boyshorts with a false fly. I got under the covers and immediate put my hand on the back of B’s thigh to stroke the soft skin there. B neither moved out of the way, nor closer to my touch, so I kept at it to get a reaction one way or another.

I began tracing the line between the cotton of B’s panties and the soft skin of her ass, eventually bringing my finger between her legs and up the front. With my thumb, I pushed the fabric out of the way and let my finger trace the outline of her pussy lips, where I could feel a trace of moisture. I let one finger slip between her lips and found her wet. With one hand, I pulled the crotch of her panties out of the way so that I could work on her with my other hand. I curled my thumb in to bump her G spot and used two fingers on the outside to tease her clit. After a couple of minutes of this stimulation, B parted her legs slightly to give me better access. I pulled my thumb out and rested it on her perineum and held my index finger hard against her clit with one fingertip parting her lips. She clenched against my hand several times as she came.

Main Event: The least inspiring since I began keeping this diary (although thankfully far from the worse of our sex life together!) I get so turned on turning B on that it’s nearly impossible for me to get her off and not get off myself. B knows this, and slipped off her briefs as I took off my shorts. Once again, I climbed on for fast missionary pumping, but the lack of foreplay and B’s sleepiness kept me from being fully hard, and B’s post-orgasmic slipperiness and relaxed muscles gave me even less friction — I came quickly, but only in a semi-erect state.

Afterplay and Afterglow: None.

Rating: ★ [Saved for the times when I'm so soft during the act that I regret putting B through it, though she may have awarded two or three for her orgasm.]