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First night with Elisa, a 30 yr old divorced woman.
To give a little context, Elisa was my next girlfriend after Sheryl (you can read about Sheryl on my earlier stories). Physically Elisa was somewhat a 180 from Sheryl, she was about the same height though, and as I would find out over our nearly 5 year relationship loved to have sex and willing to try most things.

A little about Elisa is that she was recently divorced and had one son who was about ten when we started going out. She had been married for about 10 yrs and from what she said had very little intimacy during her marriage. She was 5'4" (long legs though), black hair which was either shoulder length or a little longer, curvy figure, brown eyes and great smile. Her breasts were fantastic, easily 34d or so. She always wore thongs and liked having a landing strip perfectly trimmed. She was 30 yrs old and not having been that intimate during her marriage she had a lot of stamina in her and a lot of sexual needs that had remained un exploited – as I would find out.

We started going out for drinks etc. as we had mutual friends. At first nothing came of it and we were just having fun drinking and going to movies. One night we had a few drinks and kissed while we were dancing, and after that we started going out more and more but we held back being intimate for weeks. I honestly wasn’t sure if I wanted to have a relationship with a divorced woman as it brings an additional complication that a normal relationship doesn’t.

The first time we had sex it was during a trip to the beach. We were guests in a house of a friend of her, we were to stay overnight and drive back to the city the next day. At first, she wasn’t sure if to ask her friend if we could sleep in the same room because she didn’t want anyone to know we were trying to go steady, but at the end she decided she would ask if we could sleep on the same room, so we did.

I honestly didn’t even think we would have sex that night as up to that point we had both just been trying to get to know each other. It had been a long day so we went into the room pretty early; we both went to sleep pretty quickly. At around midnight she woke up to go to the restroom, this woke me up. When she was walking back from the bathroom I could see her figure through the semi dark room, she had a grin on her face I can’t explain, she didn’t know I was awake and watching her as my eyes were half shut. She was wearing a t shirt that ended half way up her thigh, her 34d breast were fully erect and I could see her nipples thru the t-shirt. She climbed into bed, spooned me and starting touching my leg and chest to wake me up. I faked I was waking up and asked her if everything was alright, she said “yes everything is fine, and will be even better shortly”. Everyone else in the house was asleep but we were sleeping in the room next to her friend so she was trying to make little noise and was whispering into my ear.

The starting massages my butt cheeks and soon placed her hand in my half-awake dick. As soon as she did that she said “you know, I’m on pills, I have been on them years since I didn’t want to get pregnant again with my husband… I only say that in case you are interested”. As soon as she said that she rolled me on my back and sat on top of me, looking me straight into my eyes.

The view was incredible, even when she was still wearing her t-shirt, her voluptuous breasts and her semi innocent grin we driving me crazy. I nodded to signal ‘yes’ and as soon as I did she started kissing me passionately while massaging my balls and dick with her hand. She whispered into my ear, “I’m sorry if I seem out of practice but I haven’t done this in years. The only thing I ask for you is that you please let me be on top. I want to move at my own pace and watch your face as I make you cum. Oh and remember, you can’t make too much noise”.. she then winked at me.

She then sat back up and removed her t-shirt... I was in heaven looking at those perfect breasts, them she slide her thong to one side, grabbed my penis and started playing with it, rubbing my head all over her clit and sometimes faking she was doing to put it in her. That foreplay lasted for a few minutes, all I was thinking was omg, this feels soooo good and at the same time I was reminding myself I needed to last long enough for her to enjoy, if not cum.

Throughout all this I was grabbing her breasts with my hands, they each were able to fill my hands fully, from time to time I would grab her throat and choke her just a bit (which is something Sheryl would love, so I wanted to see how it went with Elisa).

All of a sudden, she looked at me, moved her lips without speaking and ‘said’ “ok here we go, I’m ready”, she then grabbed my penis and inserted it into her vagina. I can’t believe how wet she was, it slid right through. My first thought was ‘omg, she is really tight… she must not have had a lot of sex”… she was moving her hips back and forth really slowly and watching the roof a lot in order to get full penetration. When she would look at me she would be biting her lip and exhaling silently. She then started leaning back and grabbing my balls as she continued to grind my dick, which was putting me over the edge…, she could clearly see this. She looked at me and again, without verbalizing just moving her lips she said “cum inside me, I want you to cum in me”. As soon as she said that she fixed her eyes on me and starting moving faster and faster… the bed was definitely rocking. Not sure how she timed this, but as soon as I was to burst, she stopped moving and she made my dick go deep in her… I came like never before.. it was one of the best orgasms I’ve had.

Soon it was over, she grabbed a towel to clean herself up a little bit and then laid next to me regaining her breath. I was completely recovering from my orgasm. We both fell asleep pretty quickly after that. The next morning, when we woke up the first thing she said to me with a smile on her face was “you know, I also swallow”.. then left the room.

In the months and years to come we had plenty of great nights which I hope to write about in the near future. Hope you liked this story!...
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