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Elaine's First Time


robert smith

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  • 2 weeks later...
  • 2 weeks later...

This is about the first time we hooked up with Mike.  He became our first FWB.  He was the first man we had ever thought about having sex with that we had known as a friend for several years.  He had even worked for me a couple of summers while in college.  We had gone out on a couple of dinner dates and to the movies with him and his date. He did not have a long term relationship with any of these girls.  One evening while I was talking to Elaine about trying to find someone to fuck she said "What about Mike?",  I was surprised because she had always wanted to do people she did not know or were not considered good friends.  I said "Are you sure?".  She said he was everything she liked in a man, tall, good looking, had recently broke up with his GF and we were already good friends.  I agreed but just wanted to make sure she was okay with it. He was 25 and we were about 40.  We had never tried to seduce someone we knew this well and were a bit uncertain of what approach to use. Many men actually get nervous and hesitant about 3 way sex so we finally decided to just surprise him and hope for the best.

We invited him to our house for dinner and drinks.  I cooked steaks outside on the grill and we enjoyed the food and wine.  After dinner and some small talk I said we had a surprise present for him.  I told Elaine to go get it for him.  We had obviously discussed this and set it up in advance.  She had her lingerie already set out along with her lipstick for a quick freshen up.  While she was upstairs changing he looked at me kind of funny and said "What's the deal?".  I said we had done this before and always liked it and thought we should share our fun with him.  He just looked at me like what the hell are you talking about.  I smiled and said you will know in a minute or two.  We were in our living room and I had sat in the chair next to the couch making sure he sat there.  I set our drinks on the coffee table.  When I heard Elaine walking down the stairs I told him to close his eyes for a few seconds.  When he opened them Elaine was standing in front of him dressed in this outfit.  He was speechless.  These pics are not from that evening but are the outfit she was wearing. 

To say he was flabbergasted would be an understatement.  He kept switching his eyes from me to Elaine.  I smiled and said  "Go ahead and get started.  I will just watch for a bit before joining".   He said "You mean we are going to Tag Team her?"  I smiled as Elaine moved to the couch and sat on his lap.  She wrapped her arms around his neck and said  "Mike, I am going to show you how a real woman fucks and make you forget those young girls."  She kissed him and said  "Well, are you ready?"  I think he was still in shock as Elaine got off his lap and told him to stand up. She unbuckled his pants and pulled them down with his undies and bent down to suck his cock. Soon she had him hard. She stood up and said "Let's go to the bedroom. You two are too big to fuck on this couch".

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I loved that we were all so comfortable with each other.  She just took charge from the start when she took us to the bedroom so we could have more room to fuck her.  When he worked for our construction company we had a rule with the employees that if they broke something they had to pay for it. It was more of a threat than actual policy.  Just a way to keep them on their toes.  I am saying all that to explain this.  I have said before that Elaine will let a man cum where he wants.  Sometimes she just tells them and sometimes they ask Mike had been fucking her for quite awhile in several positions and said he was about to cum.  She said just go for it.  Most guys tell her or ask if they can cum some specific place.  He was doing her missionary style with her ass on a pillow and holding her legs up when he suddenly pulls out, grabs his cock and pumps several large blasts all over her.  It went over the front of her basque, tits, neck, face and hair.  We were both kind of shocked and when she recovered and asked for a towel.  As she wiped off her face she looked at him laughingly and said, "You are going to have to pay to have my outfit Drycleaned".  Just the first of many fun times.  She was squeezing her arms together on this pic trying to make her tits look bigger.  Had me shoot the photo aiming up to even make them appear larger than they are. 

Later when we were just talking she asked him about the big pull out and blasting her with cum.  He started to apologize and she interrupted and said she actually enjoyed it as it reminded her of her favorite porn actor Peter North and how he cums in a lot of his movies.  Mike said he watched porn with men cumming on women a lot but none of his GF s wanted him to do it.  He also said none of them had ever worn a basque and hose and the entire scene made him think of porn movies so he pulled and let it fly.  He said his cock wasn't as big as Peter Norths but he would cum wherever she wanted him to.  She said "Let's start round two"

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I always wondered why men would choose to cum on her instead of in her.  I always preferred finishing in her pussy or mouth.  Once Elaine had an orgasm or two she was content to let the man cum where he wanted.  For me getting Elaine on her knees, grabbing her hips and fucking hard and fast was my choice.  Never understood why some men chose to blast her tits, face, ass and one guy was sucking her missionary style and pulled out, yanked off his condom and covered the outside of her pussy and pube with his cum.  Different stroke for different folks.

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  • 3 weeks later...

I don't think this story is worthy of adding to my collection of our sexual adventures but thought you might get a smile out of it. When I posted this old pic that was framed on our dresser I looked more closely and realized she was wearing her "short, short blue jean shorts" We used to go to the lake and spend many hours on the water. She put these little shorts on over her tiny bikini bottoms when we would go to docks to get gas or sometimes go into their bar/restaurant. I talked her into modifying them by cutting the legs, front and back, extremely short. About the only part of the jeans that went between legs was the seam. She even cut the front pocket linings out so they wouldn't disturb the view. Since she had her suit on under the jeans she did not feel she was really being too extreme. She finally got up the nerve to wear them commando in the evening around the campfire with skimpy top if there was a guy there she might want to tease. Just another great memory brought back by posting these old photos

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