Elaine's First Time


Jan 5, 2020
With the increasing popularity of the internet I started making contacts with guys on some of the dating type sites like Adult Friend Finder. I posted some sexy photos of Elaine and said we were looking for guys interested in MMF fun with us. Many of the men, or boys, were just lurkers or big talkers. Most would not come thru with current photos or actually set up a date and time to meet. Eventually I talked to a guy who seemed legitimate. He was in his 40s, divorced, and lived about an hour away. Elaine had not met him, but was content to go along and told me to set it up. We rented a room at hotel near the interstate highway close to our new friend's town. His name was Ron and we were to meet at 8 p.m. Elaine and I got there about 6:30 checked in. She showered and dressed for the soon to be evening of fun.

Ron and I had talked via the internet about our sexual likes and dislikes. I mentioned Elaine enjoyed watching porn and sex toys. When he knocked on the door he was holding a suitcase. We all introduced ourselves and made cocktails and settled down to chit chat for a bit. I asked Ron what was in the suitcase and he opened it up and we all laughed. He had brought a VCR machine, some porn tapes and a collection of dildos and vibratiors still in the box. This was before DVDs and porn was available on all hotel room T.V.s. That broke the ice as we had Elaine look thru the tape selection as Ron figured out how to hook it up. When she handed me a tape I said she should pick out a sex toy. I popped the tape in and Elaine sat down on Ron's lap and gave him a kiss. She was in a dress with lingerie and hose on underneath. While sitting on his lap Ron slowly slid his hand up Elaine's thigh. When he encountered the top of the hose he smiled and said "I can't believe you are wearing hose. It is one of my favorite turn ons." Elaine just smiled and pulled her dress up above her hose tops and said "Glad you like them". It was a small room with just a couple of chairs. I watched the two of them kiss and fondle each other for awhile. Some guys can't get enough of her boobs and other guys go straight to her pussy. Ron seemed intrigued by her tits.

While they continued playing with each other I stood up, walked over to them, unzipped Elaine's dress and slipped it over her head exposing her lovely basque. I twirled Elaine around like a model, showing her off her body. Ron had been feeling her up but on the outside of her dress. I reached around her from the back and pulled the top of her basque down exposing her tits. Ron stood up, bent down a little and kissed her nipples. She shimmied a little and led us to the bed. Ron was exploring her boobs and I was licking her pussy. After several minutes Ron straddled her chest as she was on her back. Elaine pushed her boobs together and he began titty fucking her. She was getting good and wet so I reached for the dildo she had chosen earlier and pushed it inside her while she was playing with Ron's dick between her boobs. Elaine grabbed his ass and pulled him to her mouth. I knew the great feeling of Elaine's warm mouth and figured he would want to keep his cock going down her throat so I began licking her clit while ramming the dildo in and out of her pussy. One of Elaine's best skills is cocksucking and swallowing. I had told Elaine early in our wife sharing experiences that most guys don't have wives or girlfriends who suck and swallow as good as she can. Soon Ron was screaming and shooting off in her mouth. True to form Elaine held on tight and swallowed his cum. I kept up the pace with the dildo and my tongue and Elaine started writhing with her first orgasm. What a start to the evening.

After relaxing a bit we got going again. Elaine sucked Ron hard and slipped a condom over his dick. He mounted her missionary style and I enjoyed watching them screw for awhile. We alternated fucking Elaine in various positions. The second round of sex is always more relaxed. Elaine had learned to preform a little for me. She would smile or wink at me while getting drilled or sucking cock. Sometimes she would talk and ask me if I liked what she was doing. Eventually I was laying on my back with Elaine in front of me on all fours blowing me. Ron was standing up fucking her doggy style. I had seen him put on a condom earlier so when he grabbed her hips and started cumming I didn't think anything other than it would be my turn now. When he finished cumming he pulled out he held on to Elaine's waist and kind of pushed her on top of me. That is her favorite position and she seemed to be getting close to climaxing. She was very wet and at first I thought it was just her juices. As Elaine was grinding on my cock I could not believe how wet and loose her pussy was. Her juices were oozing down my dick and onto my balls. Her pussy felt different and I just thought she was really turned on. Ron was massaging her tits and tweaking her nipples. I said "My God you are wet!". Then he winked at me and picked up a condom from the floor that was empty. We both smiled as Elaine orgasmed followed quickly by me shooting off. I don't know if it was physical or psychological but I loved fucking Elaine after Ron had climaxed in her. I was hooked on sloppy seconds after that. As Elaine rolled off me she noticed how wet we both were. She said something about us making a big mess. Ron and I smiled at each other and Elaine looked at us as asked what we were grinning about. He held up the empty condom and I said "You just gave me sloppy seconds and I loved it". View attachment 86734View attachment 86735View attachment 86736View attachment 86737View attachment 86738View attachment 86739View attachment 86740She was kind of upset at first, but calmed down and finally said it was okay with her if it was okay with me. Most guys wore rubbers after that, but if we knew and trusted him Elaine would let them cum in her just so I could have the thrill of fucking her cum filled pussy. This was the little basques she wore
WOW what an erotic lady, I'd fuck her instantly if she lay like that for me
Jan 8, 2020
Found a few more
Elaine was looking for something in her closet and found a couple drawer full of old lingerie.I teased her about never throwing anything away. Kind of tame but great memories for me. Here is little lace thing she could put on when she did not want to mess with hose, garters, etc. Watching porn and warming herself upView attachment 335557View attachment 335558View attachment 335559View attachment 335560View attachment 335561View attachment 335562View attachment 335563View attachment 335564View attachment 335565View attachment 335566View attachment 335567View attachment 335568
I would love to shoot my hot load all over those perfect breasts, while watching you ram that vibrator in your slippery hole!