Had One Last Single Run.. The Ex's Former Best Friend [MF] | 2016

So about two years ago I ended a 5 year relationship and had a 4 month period on Christian Mingle that to my surprise ended up as one of the best runs of my life. Since that single run has now ended figured I would share the highlights for your consideration. My second conquest was not from the dating site though, but it is a story I have to share

First Conquest: http://www.reddit.com/r/gonewildstories/comments/2x0mv8/had_one_last_single_run_the_24_year_old_milf_mf/

(Backstory..skip ahead if you just want the sex) So this has a little more back-story since it is necessary. What caused my breakup was the fact my ex legitimately went crazy. I know you say "hey all do", but she legitimately had a screw come loose and the last year and a half was spent with her in and out of hospitals and therapy.

Stephanie was her childhood best friend and her college roommate. Stephanie came from money and very protective parents. She was the prototype good girl until she was on her own in college where she rebelled and started chasing the wrong guys and hanging with different people. My ex and her remained super close friends but their Senior year of College Stephanie became friends with a girl name Ellie. They partied hard and would casually hookup. Allie, my ex, was possessive of her friend and jealous.

Our first summer dating Steph invited us to her parent's beach house for the week. We had only been together a few months and I had not met Steph before, only in pictures. The first time I saw her I was instantly attracted. She was laying out getting sun and wearing a tiny purple bikini. She was maybe 5'4..but appeared taller because of her tone legs. She had a tone, tiny waist and well done implants. When I got to see her ass it was probably her best feature, disproportionately large to her tiny frame.

It was killing me all week seeing Steph wear her bikini's that seemed a size too small. She was very high maintenance emotionally and constantly seeking out attention. The second to last night we all went to a local beach bar (Steph's sister and her fiancee were also there). We played beer pong with the locals and got very drunk. At one point a local guy became mouthy with Steph and her sister over shots he bought them and they walked away right after. I stepped in and Stephanie spent the rest of the night by my hip before we went home.

On the car ride home Allie mentioned how she couldn't wait to take a shower in the huge master bath.. to my pleasant surprise Steph immediately piper in with "I want to join!". The walk in shower was huge and all three of us showered. Allie though made it clear I wasn't to touch Steph and vice versa. Out of the shower it led to all three of us having a pseudo 3-some. Allie and Steph finally hooked up but Steph and I only had limited contact. I was only allowed to finger her while she went down on Allie. The majority of my time was spent either fucking my girlfriend or getting head from her.. which I was cool with.. though I wanted Steph. I had to sneak away to masturbate the next day thinking of her.

We would see Steph irregularly over the course of our relationship. We only had one other intimate time with her, though not nearly as wild. We had went to a concert together as a large group and she stayed at our apartment. In a heavily drunk state her and Allie took a bubble bath together. I got to watch but nothing happened beyond that as Allie was horny and made me fuck her right after and Steph crashed on the couch.

The last time I saw Steph was at a Super Bowl Party a month before the breakup. She brought a date named Justin. He was a likable guy but not her normal "bad boy", quite the opposite. He was a bit dorky but followed her like a puppy. Steph knew the troubles I was dealing with and pulled me aside before leaving to ask how she was.. she hugged me bye and told me to call if I needed anything.

Once the breakup became Facebook official I received numerous messages from friends and the occasional ex asking what happened and how I was doing. I kept Allie's problems under lock and key.. only a handful of people knew her struggles and only myself and her parents REALLY knew the extent. Steph's message was simple "Sorry to see it happen. You good? Text or call so we can chat."

Since she was one of the few who knew what I dealt with I sent her a text and we conversed over the next week. Nothing crazy..just the subject at hand for the most part. By the end of the week we had talked about some "good times" including mentions to our week at the beach or laughing about the concert. The end of the conversation came when she offered me to come over for dinner that she would cook at her place because "it might be good for you just to talk about it and get it out". I agreed. I am glad I did.

Stephanie worked a desk job for her dad's company and did some promo modeling on the side... but it was clear her town home was a gift from her dad. It was a new updated two bedroom she had all to herself. When I came in I was surprised. She met me with a giant hug just inside the door, she was wearing a white t-shirt a size too small and the tiniest cotton shorts that he ass barely crept out of.

She made some pasta with chicken and Steamed Green Beans. We drank wine..which she had already drank half of a bottle of before I got there. By the end of dinner she had to be 4 glasses in. We retired to her couch where we sat maybe 3 minutes before she stated "You haven't been here before have you? Let me give you the tour!". She showed me around and the last stop was the deck. On it sat a hot tub steaming in the chilly night.

" God that looks good on a cold night like this!", I said. "We still have wine to finish....", she responded making a goofy face and motioning her arms like a Price is Right model. "I wish. I don't have anything to wear." "We are private..just wear your boxers (I actually had on boxer briefs).. I get in it naked all the time"

It did look good and the prospect of Steph in a bikini lured me in so I said "Sure. Bring the wine". I stripped down to my boxer briefs as Steph went inside and eased into the hot tub that felt amazing. I could hear her sprinting up the steps inside and a few minutes later she came outside wrapped in a plush bath robe. Wine bottle and glasses in tow.She turned on the jets and poured us each a glass before disrobing. It appeared to be the exact purple bathing suit from some years before.. her body as amazing as it ever was.

"I always liked that bathing suit" "When did I wear it?", she asked. "When we went to the beach..it's what you had on the first time I met you" "Holy crap you have a good memory. That is right! I am glad it still fits".. she smiled almost blushing it seemed.

She sat on my right with a little distance. We continued talking..the conversation now about our current lives, work, mutual friends. I felt her legs as she placed them across mine and din't know how to read it so I asked about how things were with Justin. I'd be lying if I hadn't noticed that despite numerous pictures with him she still had not made it "Facebook Official"

"I don't know.. he's sweet and all but he's not my type."

We finished our glass of wine and she couldn't reach the bottle so she got up to refresh our glasses. This time she carried them in with her and sat right next to me. Her hand rested on my upper leg and she massaged me as we continued talking. She eventually turned her back and leaned forward..pulling my hand up. "Scratch my shoulder blade..hurry..hurry" I did and she let out a sigh of relief. With my hand already there I started massaging her shoulders hesitantly. "Ummm" is all she said in obvious approval. By the time we had finished our last glass of wine she was leaned back against me eyes closed as I was deeply massaging her lower back and rubbing my hands deep tracing the curves of her side and arms.

"I am getting pruney", she said showing me her wrinkled fingers. "Better head inside."

I stepped out first. My wet underwear sticking to me revealing my semi-hard penis. She followed behind and stood for a second shivering and making a sound to reflect it. I picked her robe up and wrapped her and hugged her with it rubbing her back to warm her. She took my hand and led me inside. I paused to gather my jeans and shirt, I tried to remove my hand to get my shoes and socks but she grabbed me saying "You ain't leaving yet..get them before you go"

She led me upstairs to her master bedroom and through the french doors into her master bath. She removed her robe and hung it on a hook then grabbed a towel and wrapped around my waist and then hugged me again. Then things escalated. "You have seen me naked before.. you don't mind if I change?" I don't think I said or did anything. She removed her bathing suit and stood before my staring eyes. "OK.. this is between me and you!" She then unwrapped my towel and placed her hands on the elastic of my boxer briefs and pulled them off. She took my cock into her hand and closed her eyes looking up at me and we kissed.

We made out for a bit exploring with our hands standing there. I picked her up and carried her back into the bedroom and placed her on top of her bed and began going down on her. She pushed my head deep inside her. Usually I work the clit the most but Steph forced my tongue as deep as it would go.. bobbing me. I slipped two fingers into her and she arched back I then went back to work licking her clit. She came quickly. Steph was very quite in bed...her approval given by deep breathes and the occasional "unn-huh". When she came she would hold her breathe and push me deep into her before releasing with a single "Fuuuccck"

I lay next to her as she caught her breathe thinking that was it, to my surprise she immediately crawled on top of me and grabbed my cock positioning it and then rapidly sinking down onto it.

"Hold on..I don't have a condom" I said trying to withdraw. She wouldn't let me,,, pushing herself down harder.

"We're good. You are clean right?", she answered. I was.

She rode me like I have never been rode before. She pressed so hard down onto me my hips would be sore the next day and a half..grinding front to back wanting to feel all my length and girth.

In an ironic twist.. contrary to my previous hookup the very quite Steph suddenly did the trash talking. "Tell me I am tight" (True), "You have always wanted to take me" (True), "I am prettier than Allie" (True)... I was close to cumming and didn't want to go so fast. I flipped her over and pulled out in a hurry..sinking down to eat her out some more.

"Your teasing me! I want your cock!", nonetheless she moved her hips and arched with every flip of my tongue. I got my impending orgasm under control and eased back up her body to missionary to re-enter her. I resumed with slow deep thrusts. She dug her nails deep into my back..it actually hurt but I wasn't about to let her know. "Faster...Faster" she said very quietly. I obliged. Soon I was going as fast as I could.. she wrapped her legs around me tightly and orgasmed a second time with the same signature "Fuuuuck"

The sound of her cumming and her vagina gripping in response had me ready. I pulled out and shot two strings of cum. One from her right nipple to her lower side... the other above and into her navel. We caught our wind and she told me where her wash cloths were. I cleaned her up and we laughed about the tiny pool of cum inside her belly button.

I dressed myself.. going commando due to wet underwear. She walked me downstairs still naked and I gathered my socks and shoes. As I put them on inside she remarked how I was making her leak.. her juices and my pre-cum forming a frothy discharge. It was a bit awkward with the hormones dying down so we just kissed goodbye.

I didn't know what happened and frankly was a little worried of the fallout so I didn't reach out to her. She sent me a smiley face text the next night and then "Ummm... that was well worth the wait. :)". I responded once and she called me. We talked for an hour and I was very relieved to know she just wanted it to be a lone act that was the culmination of a whole mess of emotions that had never been resolved between me, her, and Allie. She actually revealed her and Justin were closer than she let on, but she had made her mind up she wanted to have sex with me while she ahd the chance and knew I wouldn't have went through with it otherwise. We agreed that we needed to let it die and if we were both single down the road to re-open it then. After all that she said that I could come over right then for one last round if I wanted before we put it to bed... I told her it probably wouldn't be wise. She agreed.

Fast forward and she married Justin. We never spoke of that night except for a double date over a year later when she purposely worked "I wouldn't mind finding a hot tub somewhere" while looking at me out of the corner of her eye and smiling.