This is a true story. I changed the names of all and some details to disguise the identities of those in this story. The dialogues are to the best of my memory. It has been more than 45 years since this happened so I hope you will cut me some slack.
[Background: In 1978 I was involved in a hot wife/cuckold/bull relationship. Janet was the hot wife; Derek, my boss, was her cuckold husband. Our HW/C/B relationship had been on and off for more than two years. If you want to read about my experiences with Janet and Derek they are on my profile page.
This is the first of two stories focused on my initial times with Connie, Janet’s BBW MILF BFF. There will be no PIV sex action in this story. That will be in Part 2.]
**Connie and I, our first time together**
Each year, May through September, Derek and Janet hosted a monthly cookout at their huge house (actually it was Janet’s house). Derek always invited his team members and their families; Janet always invited some of her family and some of her long time friends and their families.
Two of Janet’s friends who always attended were Connie and her husband Carl. Connie and Janet had been best friends since high school. They had a long history together when it came to boys and men. Some of that history was pretty hot but those stories will have to be told some other time.
After a post-cookout sex session one summer Friday night, Janet asked me if I thought her best friend Connie was sexy. I told her I thought she was very sexy. Connie was 5′ 10″ 185 lbs with curly black hair and blue eyes. She was very pretty with a little turned up nose and perfect white teeth that gave her a great smile. She had been a cheerleader a state university and had a cheerful and flirtatious personality. She was a good dresser, always the best of the women at the cookouts. She was what we now call a MILF. Two other things, Connie had some big tits and her ass was wide – she was a BBW MILF.
Carl was 6′ 3″, 265 lbs, former college basketball player, blond Nordic looking guy. He was a drunk; he got stumbling drunk at every cookout and someone had to help Connie get him home and into bed.
Janet asked me if I would like to fuck Connie. (Of course I did but I tried to play it cool. I thought this might be some kind of trick question.) I asked her why. Janet said Connie hasn’t had sex in years and that Connie was envious of her having sex with me. Janet, being a good friend, had offered my services to her. I told Janet I was sure it would be great to roll in hay with Connie but I did not know how to pull it off.
No problem said Janet; she and Connie had cooked up a scheme. I was to help Connie take Carl home and put him to bed. Connie and I were then going to enjoy each other. The idea of fucking Connie was delicious to me. She and I had flirted several times when the two of us were alone at the cookouts (she liked to rub her ass against my crotch). I couldn’t wait to get my hands on her.
At the next cookout we put the plan into effect. When the cookout ended I helped Connie get Carl into their car, followed her to their house and helped her get Carl in bed. We got him out of his sneakers, socks and shorts. Connie told me she always gave him aspirin and “something to help him sleep”. She got a glass of water and two aspirins and two OTC ‘sleeping aid’ pills. I propped Carl up and she got him to take them. I eased him down, she covered him up, we turned off the lights and shut the door.
We walked back to the living room and sat on the sofa. She was dressed in white sneakers, loose white shorts and a rather low cut, tight blue and white blouse that showed off her deep cleavage. Connie said it would take a while for the sleep aids to take effect. So we talked about the cookout, kids playing at the cookout and what a beautiful evening it was. We fell silent for a minute. Connie said quietly “He will be sleeping for hours”. I took that to mean she felt it safe for us to get friendly.
I moved next to her, put a hand behind her head, pulled her to me and kissed her lightly on the lips. I leaned back looking for a response. Connie said “That was nice”. She leaned toward me and gave me a more forceful kiss. Oh yeah. Connie knew how to kiss.
We began kissing and touching each other. I started playing with Connie’s big tits; she started running her hands up and down my arms and then up and down my thighs and then she moved one hand to my shorts over my cock. She squeezed my cock and gave a little ‘hmm’ as we kissed. She stopped kissing me and looked down at her hand over my tool. She looked up at me and smiled.
Connie slid to the floor, unbuckled my belt, pulled down my shorts and underwear. She looked at my cock and balls for a few seconds and then took them gently into her hands. She stroked my cock a few times and then dropped her head to take my cock head into her married mouth.
Connie began to give me a blow job. Not just a plain vanilla blow job. She began to give me a great blow job. She knew all the tricks; head licking; running her lips up and down my shaft; licking, sucking and rubbing my balls; taking my cock completely into her mouth. All this time I had my hands in her beautiful black hair helping move her head up and down my shaft when she went down on it.
Sometimes she would stop and kiss my thighs and then resume the blow job. She was slow and methodical. She said nothing but ‘um’ from time to time, as she worked her magic. After a good 15 minutes I told her I was about to shoot. Connie did not miss a beat. She took my cock deeply into her mouth and I came as I pressed her head down and lifted my hips to get as much of my dick into her mouth as possible.
Connie swallowed it all with no gagging or coughing. She lifted her head and smiled a little smile. She bent down and gave my cock a few light kisses and told me tasted good. She pulled up my underwear and shorts. I helped her up and she said she would be right back. She walked down to hallway to the master bath and the bedroom where Carl was sleeping.
After a few minutes she came back making a detour to the kitchen for two beers. She sat next to me and we cuddled as we drank and talked. She said Carl was asleep and would sleep until the morning. She asked me a few questions about Janet and me and Derek. It was obvious she did not think much of Derek. She pointed asked if Janet and I saw each other without Derek’s knowledge.
I told her we did from time to time but that was because Derek went through periods of insecurity about our (Janet and me) relationship. I told her Janet sometimes visited me at my apartment before going to her home after work. That seemed to spark something in Connie and she moved up to me and we began kissing with some more passion.
I unbuttoned her blouse and wrestled one of her big tits out of her simple white bra. I played with that monster for a while and then began to lick and suck its nipple. Connie had her hands at the back of my head and was making ‘oh’ and ‘um’ sounds as I licked and suck it. After a few minutes she grabbed my head, pulled it away from her tit and leaned down to kiss me with everything she had.
I moved my left hand from her tit to between her legs and felt her pussy heat. She spread her legs and I began to slowly but forcefully rub her pussy mound. We were kissing and our tongues were exploring each other’s mouths and lips. I started to smell her pussy; it was intoxicating. I had never smelled a woman’s scent that seemed so enticing. It made me desire her as I had never desired any other woman before. My cock was hard; I was eager to take this woman.
She put a hand on the back of my left hand and she said “Faster”. I started to rub her furiously; I could feel the heat build up from the friction of my hand rubbing. Connie let out a groan and pressed my hand tightly against her pussy. Her body stiffened and then shook. She let an ‘um’ and her body relaxed.
She looked in my eyes and and said “Kiss me”. We kissed for several minutes and then she leaned into me holding me tight. We stayed like that for several minutes. She felt soft and warm against my body. I stroked her hair slowly enjoying its feel in my hand.
I was very hard and thought it was time for us to take the next step. I started to play with her exposed nipple and I felt it tighten up to a firm nub. She was looking up at me with relaxed dreamy eyes.
I asked her to stand up and suddenly she got a look of panic on her face. Connie said she couldn’t go on as she wasn’t sure of what she was doing. She told me she was so sorry but she wanted me to leave. She said she need to think about what she and I were doing.
She walked me to the door and gave me a full wet kiss tasting of cum and beer. She told me she was sorry again. She apologized for leaving me in my current state. She said “Maybe next month” as I stepped out the door.
I was aroused and confused. I thought things were going well and then I get the bum’s rush from her. I drove back to Janet’s home. She took me directly to the master bedroom, pushed me onto my back and yanked down my shorts and underwear. She grabbed my cock and started kissing and licking it. She told me to describe every thing that happened. I did. When she found out Connie and I had not had sex she flipped out.
She went on a rant calling Connie a big talker and a fucking tease. She told me they had spent hours talking about how I was going get alone with her and Connie had told her how much she wanted to fuck me. After a while Janet calmed down and we undressed and got under the covers and fell into each others arms. We snuggled and she asked me to retell what happened.
I did and she started to blow me as I described Connie’s blow job. She tried to recreate Connie’s BJ and she did a very good version. But it wasn’t as good as Connie’s. After she finished she asked if her BJ was better than Connie’s. I told her it was much better than Connie’s as that is what she wanted to hear.
We made love later that night as we usually did when we got together. And, as usual, after I finished in her, she went down the hall to Derek so he could eat my cum out of his wife’s pussy. It was sex and cuckolding as the three of us had grown accustomed to in our time together.
That is enough for now. I will put up Part 2 when I can.
I hope you enjoyed reading about my first session with Connie as much as I enjoyed Connie’s blow job.
Source: reddit.com/r/sexystories/comments/tiydlt/i_tried_to_bang_janets_bff_connie_after_a_cookout