Chapter 1: The begining + Sheryl 1
Introduction:
Sheryl steps up to the plate
Beth: we dated for about 1 yr. I was 21 she was 24. She was 5ft 3in, light brown hair shoulder length hair and green eyes. She had sort of a tomboy looking body, sort of thick legs but had a perfect ab and nice breasts (cup B size). She lived with her sister in a two bedroom apt.
Sheryl: we dated for about 3 hrs. I was 27 and she was 35. She was 5ft 6in, blonde hair shoulder length hair and deep blue eyes. She was the classical executive woman, nice body and legs, her abs were nice although less athletic than Beth’s. Her butt was amazing; it was perfect and looked great on jeans or pants, very firm. Her breasts were smaller than beth’s too (cup A size), but she sure made it up with her drive. We worked in the same firm, worked in the same building and floor.
The stories for each relationship are in chronological order so you can see how the relationships changed over time.
Sheryl 1:
I was attracted to Sheryl since the first time I saw her. She had that classic executive look and was always well dressed with suits and high heels, strong personality. She wore a lot of jewelry and necklaces which made her look sort of exotic. I honestly never thought anything would happen, I was younger than her and with her looks I was sure she had a boyfriend.
We started going out for coffee at work with other coworkers, very casual. Soon we found out we hid it off a lot, we both like foreign languages (we often spoke in Spanish and Italian), liked drinking beer and traveling. Our senses of humor were very compatible: sarcastic and sexual humor, quick with the jokes and double meaning comments.
The first time something happened it was a Sunday night. We had been at a coworker’s party on Friday and had exchanged numbers. She had mentioned a couple of her friends were in town for the weekend, would be staying with her and she might need someone to join in on Sunday in case she was already fed up of spending time with them 24/7. We all met at a bar for lunch and drinks.
At about 5pm they went to her place to drink mojitos. I thought I was going home, but after the bill came she said I could join them for a couple of drinks if I was interested and didn’t have plans, so I joined them. After a few more drinks we were all drunk. Her friends left for a few minutes to go inside and it was only her and me in her balcony. At this point I still didn’t think anything was to happen I’m not sure why, but after taking ice from the cooler she mentioned her hands were very cold out loud. I took her hands between mine and said I would warm them up. We both looked at each other and smiled, she said thanks, you are nice. We kept talking, when hands were warm I let them go and made a move to lean fwd and pick up something close to her, she didn’t pull back, so I went in for a kiss. And she reciprocated. It was great, she was a great kisser. She stopped for a bit and said ‘ wow you are a great kisser’, closed her eyes and kept going. It was a great make out session.
We got interrupted by her friends coming out to the balcony, but the quickly went back in, but now to her room where they were sleeping in her one bedroom apt. We laughed, and moved the kissing session to her living room. We were kissing passionately, like there was mo tomorrow. By this point we were grabbing each other’s butt, I was touching her breasts (to which she said, no.. Not yet). By about midnight, we had made out a lot and I was ready to go home to masturbate. When I mentioned I was leaving, she said ‘were do you think you are going? You stay here tonight if you don’t mind sleeping with me in the couch as my friends are sleeping in my bed’. Of course I had no problem with this! But she also said ‘ but no sex ‘. To which I was fine. Here I was to sleep with this gorgeous executive woman that I had been wanting to fuck for months, certainly had masturbated to a few time over that period.
We lay down on the couch fully dressed; we were very tired after hrs. of drinking we would fall asleep, wake up kiss and fall back to sleep. By 4 am we woke up and she whispered in my ear in Spanish ‘you have to be very quiet, remember my friends are inside and can probably hear us’. I was actually lying down in front of her, she was spooning me because she wanted to have control of what was happening.
She licked my neck and ear and unzipped my pants, introduced her hand and grabbed my dick with her right hand. It was hard as hell and swelling from all the kissing and touching. I put my hand behind my back and touched her, unzipping her pants and placing my hand in her pussy, no panties! She was wet wet wet, she said ‘I’m usually shaved clean but I haven’t been with anyone in a while’. I didn’t care, I hadn’t shaved either since I hadn’t been with anyone in a while too, plus for some reason it felt hot to touch her without her shaving. She whispered in Spanish, ‘ok let me know when you are close I don’t want to clean my furniture, plus it’s new so I don’t want cum all over it. Talk to me in Spanish in case they are listening they won’t know what we are saying’
She started stroking me slowly, and then she would stop and grab my balls and lick my ear and moan. I was going insane but didn’t want to cum to early and cause a bad impression. I continued to finger too, touching her clit with my thumb. After a while it was evident that I would be the one to cum… I started breathing faster, so pick up the rhythm. In my mind I couldn’t believe my coworker Sheryl was the one doing all do. I was ready to cum, so I told her I was about done ‘good I’m glad’, she said. She slid her left hand between me and couch and was now hugging my waist, stroking me with her right hand and had placed her left hand near the head of my dick to catch my cum. I said ‘ok I’m ready..’ she then stopped stroking my and with her right hand grabbed my dick and balls and I swear she must have squeezed my cum out because I came without her actually stroking my dick. It was amazing, it felt so good and totally different from anything else anyone had done.
After a few minutes she said, ‘ok I think we should get ready for work, plus you need to catch that flight for your trip’. We turn the light on and while we were zipping up she noticed a small drop of cum on her living room table. She acted as if she was annoyed. Then walked to the table, cleaned the spot with her finger, looked at me smiled and said ‘ yummy’, she licked her finger and said ‘you taste as good as you kiss’.
I left to work, and later to the airport.
Sheryl is the most intense women I have ever met. We did thing I had only imagined of before.
