The widow (m/f) | 2016

Note: I have been very lucky to have a lot of sex with a lot of beautiful woman, so I wanted to document some of these experiences. They are all 100% true (except names). Just as a point of reference, I am often told I look like Vin Diesel (though I don't see it)-I am 6'1, 210, shaved head, blue eyes, tattoos, muscular build, mid-late 30's, live in South Florida and have a successful career. I will try to answer any and all questions! If you are looking strictly for the sex part, scroll down awhile.

I had met Risa through a mutual friend at a party; she was definitely striking, early 30's, a legitimate 10. She was about 5'5, blonde hair, blue eyes, with perfect surgically enhanced tits, and a nice stickout ass. She also had a really good sense of humor, something often missing from beautiful girls. Our conversation did turn more serious and she explained the tragedy that had happened 3 years prior; her husband had tragically died in a car accident leaving her to raise their young daughter. I told her how sorry I was to hear this; she moved the conversation back to lighter topics...one of which was sex and her lack of. Risa said that it had been 3 years since she had even kissed a man; at first busy mourning her husband and then "life" just got in the way. She joked about knowing my reputation, and insinuated that maybe we could help each other.

As it was getting late, she had to go, so I walked her to her car. We did exchange numbers, but I wanted to try to remind her about what she had been missing over these three years. I leaned her up against her car, and kissed her, she kissed me back leading to an intense makeout session against her car. I took a chance and slid my hands on to her ass and squeezed pretty hard, she moaned and pulled away. She said she had to go, and would text me tomorrow.

Around mid-morning the next day she sent me a text...it had the heading of ground rules. I am paraphrasing, but it more or less said that she wasn't looking for a boyfriend, didn't have the time nor desire for one...she said that guys were always asking her out and she didn't want a guy who was going to fall for her. But she did want sex. And she wanted to be able to hang out from time to time, no expectations, no rules...but with good sex. I felt like I hit the pussy jackpot. Let me get this straight, a beautiful woman wanted me to fuck her without any obligation to anything more-DEAL. She then told me that she had only been with her husband as they had been high school sweethearts, so she was definitely clean, but suggested we go both get tested. I do get tested regularly, so it was fine by me. I agreed to all of her terms and we made a plan to get together the following week (we had to get tested, and I was going out of town).

The following Thursday Risa called for an "appointment" as she called it. I asked if she wanted to meet for a drink, and she declined saying she would just come over. I gave her directions and got the house ready. As she hadn't had sex in years, I wanted it to be nice...I had candles going, good music, dimmed lights, and had opened a bottle of wine. I heard the doorbell and saw Risa on the other side of it; looking stunning. She was wearing black tights, and a tight low cut shirt showing off her perfect tits. I gave her a kiss on the mouth, and showed her around my house. We made a little small talk, and I could tell she was a little nervous. We had some wine and talked on the couch for a bit before deciding to head to the bedroom. I told her I would be right back, I was just going to let my dog out. When I walked back in the room, Risa had undressed to her bra and panties. They were a matching black set, her tits were popping out of her bra, and her ass looked so juicy in that thong. I would like to say I kept my cool, but that just wasn't true. I took my shirt and pants off as fast as I could, and met her at the bed.

I took control of the situation, and eased her back onto the bed, as we were kissing. I then put her on her back, and pulled her towards the end of the bed, where I removed her thong. I started by teasing her inner thighs with light kisses; I could see the wetness on her pussy as I moved closer to lick her. I took a long lick from the bottom of her pussy, and all the way back up. She let out a moan, and I went back to eating her pussy like it was my job. I eased a finger inside of her, while I was nibbling on her engorged clit; her pussy was the tightest pussy I have ever been in. Take note, this was a woman who had went through natural childbirth; there is no rhyme or reason as to why a woman may be tight or otherwise. I felt her pussy contracting on my finger, I slowly tried to insert a second while I kept licking her clit. I was able to get the second finger inside of her, and brought my head a little lower, and lightly licked her asshole (I later found out that not only had she never had her ass licked but she had only had her pussy eaten maybe 5 times in her life, her husband wasn't into it). Risa was really getting loud, as I licked her pussy/ass, while fingering her...she got a little quiet and I could tell she was going to cum (the change in breathing patterns always gives it away)....and just like that she moaned, more like a scream and completely soaked my face...I LOVED it. She didn't squirt, but she got so wet that my face was completely soaked with her pussy. As she came down from her orgasm, she smiled and pulled me off of my knees so that I was standing up in front of her while she was lying on her stomach.

I wasn't expecting much, just like her lack of experience in receiving oral, she had previously told me that she had only given oral to her husband. I was quite surprised when she grabbed my balls and the base of my cock, and spit right on it..i love when a woman spits on my cock. She gently pulled my balls as she went to work on my dick. I was shocked at how good she was, I could tell I was going to cum soon so I flipped her around; pulling her towards the edge of the bed and rubbed my cock on her pussy. She was already wet, but I knew after the fingering experience, that I had better be slow until she was comfortable with my cock (I'm not huge, but definitely not small). She lost patience and took control of my cock and started to push it inside of her, she grimaced, and I told her to take it slow...she said she wanted to be fucked and now. I pushed in a little further and sank in, she moaned. We started off pretty slow, lots of kissing. I was standing on the side of the bed, and she was laying down on her back (point of reference). We had lots of kissing, and it was really passionate. As I was sliding in and out of her she undid her bra, and made a joke about how since I didn't take it off she had to.

I told her to stand up, that I wanted to fuck her from behind...I found out later that she had never been fucked from behind, while she was deeply in love with her husband he wasn't very sexual and was very vanilla. I bent Risa over the bed and got behind her and started really fucking her hard...I had both hands on her hips, and she was really getting into it...fucking herself as hard as she could back on to my cock...after a few minutes we got on the bed and I put her on all fours-what a view-she had a great ass, and I LOVE rearview of pussy-its one of my biggest turn-ons. I started to fuck her hard from behind and reached forward to grab her hair. I could tell she was into it, as she got louder. Her breathing got a bit more intense and she started to cum again. It is a good thing because I was close to. Between the hand full of her hair, her tight pussy stroking my cock, the view of her ass/asshole...I had to cum. I gave her the obligatory "I have to cum"...and she gave me the green light to cum wherever I want. I kept thrusting as fast as I could and felt that tingling in my balls; I started to cum and cum hard. Risa moaned, told me she could feel me cumming (I don't think women can feel you actually cumming in them, i think they feel the pulsating of the cock). I must have spurted like 4-5 hard spurts and pushed as deep as i could as I began to come down from my orgasm. I took my dick out of her; i was surprised when i saw the amount i came inside of her. She was full.

We rolled over, in a sweaty mess and cuddled for a bit. We talked more, and I went out to the kitchen to get us some water. When I walked back in, she was sitting up, under the covers but with those perfect 34 D's sticking out; we started to fool around and she sucked me back to life. She said she wanted to be on top, and guided me into her cum filled pussy. I am not a fan of someone else's sloppy seconds, but have no problem fucking a pussy filled with my cum. It was definitely extra wet/messy from my cum, which for some reason turned me on more, she rode me hard...grinding her clit to the base of my dick...she came quickly, biting her lip. I was right with her, at this point she was bouncing up and down on my cock, I had my hands all over that great ass, and gently applied a little pressure to her asshole with my finger, just as i began to shoot inside of her. I later found out that it would make her cum to feel me cum inside of her; and just as I started...so did she. I filled her up again with a large load and left my cock inside of her until it eventually fell out. My crotch was a pussy soaked mess, between my two loads of cum, her orgasms,....and I loved it.

Shortly after, she jumped out of bed, got dressed...and we said our goodbyes. We continued our arrangement for about 6 months or so, until she told me she wanted more. At the time I wasn't interested in a relationship, so we parted ways. But til this day we are good friends (no sex anymore), but can always count on each other.