Too many great ones to pick. Some top contenders: First time she slipped a finger in Any time she's used both hands Any while she's driving. She can sure multitask
A buddy at work told me about a massage parlor that would give "happy endings". I went there and an older Asian lady took be back to a small room and started the massage. When she had me roll over on my back there was no hiding my excitement. Sure enough she started giving me a hand job with lotion. She was incredible. She could tell when I was about to orgasm and would stop and then start back up. She did it several times and finally continued until I exploded all over. I always remember her saying (as she was wiping up the mess) ... 'You shoot good and plenty!'
My gf and i went for a walk in the woods we stopped and started kissing. As we kissed she pulled my cock out and started stroking it.. She continued until I shot cum all over her hand.
My partner would sit up against the headboard with her legs apart. She would have me place a few pillows between her legs. I would lay on the pillows with my legs spread on top of hers. She wanted everything comfortable and in easy reach. The first time we did this, she said she's had been doing a lot of reading on hand job techniques. She used lots of silicone lube. She had all kinds of names for the different hand-job techniques. The “endless tunnel” was my favorite, and it works in both directions, inward or outward. Inward was the best. Very hard to put it into words, but OMG, insanely good. She was really good at mixing things up. The sessions would go on for a very long time, and end in a mind blowing way. The first time we did this was one of the best orgasms I've ever had. So many good/intense orgasms with her. We were together about seven years, and everything in the bedroom was awesome. This was my most recent relationship and I have to say she was by far the most fun in the bedroom.
I used to go to a place where I did mutual massage with a lady while both nude. Laid on a table using hand soap and hand held water sprayer, instead of lotions I would massage her all over then she did me. The handjobs were always great, and many let me shoot on their tits, and one slid my shaft between her thighs until I came hard.
Also, I currently see a therapist who is a lovely woman of 30. She gives a full 45-minute standard massage, paying attention to all my aches. Then she starts with the happy ending part, never rushing. Her strokes are slow and steady and I enjoy seeing in her eyes how much she enjoys doing it. I always cum hard and she cleans me with a damp towel after.
Maybe just the expression on my face. It was a large booth in the back of a dimly lit restaurant. We were sitting close and able to be cozy without looking too guilty.
Does it count if it was another guy? I would have to say the first one I had was great, I can still remember the details of that day. 12 years old I think.
