Elaine's First Time

[robert smith]

I haven't posted anything in this old thread in a long time. Almost all our Hotwife sharing stories are in the first few pages. This is a story about her revenge fuck on her husband.

It took a log time before Elaine loosemed up enought to tell me about a couple of her past experiences
I don't think I have ever posted this story. Not exactly a cuckold or hotwife situation but I thought it was hot. I wrote this to a friend and just found it.

When I first asked Elaine about previous sexual experinces as part of foreplay she was hesitant to talk about any of them. We had both been married before and she had been divorced between 3 to 4 years. Her first marriage was much more straight than my experiences, both with my first wife and while in college. I kept trying to figure out ways to get her to open up about fucking as a way to later bring up MMF sex. When I asked her to tell me if she had ever fucked a big cock she jokingly said something about "I never measured anyone". She finally told me about the one huge cock that she choose no to fuck for fear of getting hurt. I know I told you that story. Once I got her into the Hotwife LS I saw no reason to pry about past men. I knew she had started dating her husband when she was 15, got married at 18 and divorced at 26 so probably not a lot to talk about

Flash forward 20 years and neither one of us was afraid to say anything sexual for fear of embarassment. We were watching a movie or tv show where a couple had sneaked off to a deserted part of a huge library to have sex. I laughingly said I did not think that would happen in real life and she smiled and said "Oh trust me it could ''. I said tell me more. You have never mentioned that before. She just smiled and said it was not a big thing. After a few cocktails I said time to tell me.

She was going to a couple night classes in college working towards her Masters. She was a full time school teacher and her husband travelled some with his job. She suspected her hubby was or had cheated on her. When she confronted him he ended up admitted to a one night fling. Doubt that was true. LOL. They ended up staying together for maybe another year. It continued to bug her especially when he said it was just sex and did not mean anthing.

Some younger student had been flirting with quite a bit and she had ignored him. She said they were walking out of class one evening when he hit on her again. She suggested the college library. He lived in student housing and her car was very small. She had decided "One good turn deserves another". She told him to go to some quiet out of the way place. She was going to go to the bathroom, then casually walk over to where he was. She had on a skirt and she stuffed her panties in her purse and left to fuck a different man for the first time in her life. They had to stand and after kissing and groping she pulled out his cock and sucked him a bit and told him to put on his condom. She bent over and he fucked her doggy style standing up.  He came pretty fast. She lowered her skirt and said goodbye. She did not climax at all and did not care. She did not want to get caught and was probably feeling a bit guilty about her revenge fuck. This pics would be the position she was in when she got fucked

[robert smith]

I shared this with a friend yesterday.  Thought I would add it to this thred.

I have never posted this little story about our early forays into the Hotwife LS.  Elaine had agreed to try to expand our sexual horizons but turning fantasy to reality was proving difficult.  I wanted Elaine to choose an old boyfriend or lover or someone she knew and thought might be a good prospect.  She said she wanted the man to be from out of town or someone I knew but she did not.  Our first attempt at the adult bookstore was exciting and showed a willingness on her part to have sex in front of a stranger but all he got to do was play with her play with her tits and pussy while she was fucking me in the front seat of his car.  When she let him suck her nipples he shot off in her hand.

She said the sex was fun but she felt uncomfortable with a complete stranger.  I said we would keep looking.  We got invited to a pool party hosted by the owner of the business where she worked.  At least 30 to 40 people, mostly employees but some former employees and friends. Summer cocktails, beer and outside buffet food.  Typical of most swimming pool parties as late afternoon turned to the evening most of the non drinkers go home and the fun begins.

I had hinted to Elaine that she might find a potential lover.  She said she had to work with them and felt no interest in any of them.  I noticed this younger man seeming to be flirting with her.  I asked her about him and she said he worked for the company that cleaned their offices.  I said I thought he was hitting on her and she should flirt back.  She did not say anything and I hoped she was not mad at me.  A few minutes later she is in his arms in the pool. She spilled her drink and I got her a new one and hinted that she should take him to a more secluded part of the pool and see what happens. Soon they were sitting on the edge of the pool talking and it looked like some kind of fooling around.

She told me he said he had always thought she was hot but out of his class. She fondled his cock and said he got hard quickly.  He mumbled something about how he couldn't believe what was happening.  There was no place to fuck without people seeing them.  Elaine told him to sit on the edge while she got in the pool which was about up to her boobs.  She put her forearms on his thighs and pulled out his cock and started pumping his cock with her hand and her back was facing most of the rest of the people.  He asked if he could touch her boobs and said he was about to cum.  She quickly sucked his cock and he quickly filled her mouth.  She knew I was watching and she pulled the top back up on her suit and turned to face me  .She smiled at me as she opened her mouth and let his cum roll down her chin. Dropped her head under water to clean up her face and came back to sit by me.  She slyly asked  "Did I flirt good enough for you?"  and gave me a big kiss.  We went home and during our fucking I said I have to find someone to join us.  She told me to set it up and she would try it once

Obviously I took no photos of the pool party but later did find these in an old scrapbook. Never did hook up with the you man she sucked off as she found out he had a live in GF who had not gone to the party

I love the relaxed sexy smile of Elaine while he is holding her and the gleam in his eye as he is dreaming about her.  Other pic is her in our pool in same suit

The next morning Elaine had a bit of a hangover and seemed apologetic about her behavior the previous night. She said she had too much to deink and even with my encouragement she felt she carried things too far. I was afraid she was about to cry.  I gave her a big hug and said she did nothing wrong.  I jokingly said "I wished you had let him fuck you".  She appeared to be genuinely surprised when I said that.  I had to leave for some reason and said we would talk later but that I was thrilled about the party and her attitude.

That evening I asked her what she thought about Scott. He was the young man she sucked off.  She said she had thought he was a fun young guy but he had a live in GF and she still felt uncomfortable being sexual with people she knew socially.  I said some of her friends might have seen her fooling around with him.  She said we were all drunk and if anyone said anything about it at work she would say it was a "Party Foul" or she was trying to make me jealous.  We were not married at the time.  I asked her if she was willing to fuck another man if I could find one.  She said she would think about it.  I did not push anymore that evening.

A couple weeks later during foreplay she asked me if I still wanted her to have sex with another man.  I smiled and said it would be a thrill and make me love her even more.  She smiled and said something about never understanding how men think but she would try it if I set up.  She insisted he be from out of town and that she could meet him and see if we had any chemistry between the three of us.  She also wanted to be able to say no at any stage.  I told her I would start looking.
Pic was Elaine in the morning with no makeup

[cucksean]

On 5/14/2015 at 8:22 AM, robert smith said:

I have shared my wife with many men over the last 30 years.  This is how we started, kind of mild compared to some of the wilder stuff we did later,

 

   I am 61, Elaine is 59.  I met Elaine when I was 32 and she was 29.  We were both divorced with no kids.  After dating for several months I really started liking her.  I had done some swinging and wife sharing with my ex wife.  I don't think that led to our divorce, but one never knows.  I got Elaine to pose for sexy polaroid pics and she didn't seem to object like some women do.  For my birthday she surprised me with some lingerie photos done by a professional she had hired.  I was more than pleased with that attitude.  After about a year I decided to broach the idea of sharing her.  Started with sex talk in the bedroom.  While having sex she acted willing saying it might be fun, but nothing ever actually happened.  I knew for our relationship to go further I was going to have to press the issue to see if she ! was all talk and no action.  I kept telling her to pick out some guy she would like to fuck.  I didn't care if it was old lover or friend.  She said she could not approach someone about having sex with them if she really loved me. 

 

   I thought a random stranger might work.  This was in the early 80s before internet.  I had been to the local adult bookstore and seen personal ads so I posted one.  Phone numbers were not allowed.  If you wanted to respond to an ad you left your information on a 3x5 card in an envelope with the number of the ad you were answering.  You had to personally go to the bookstore to check.  I talked Elaine into going with me one night.  After checking the ad board we walked around the store.  I tried to get her to go into the movie theater section but she declined.  While wandering thru the store a nice looking well dressed older gentleman approached us and asked if we were looking for fun.  I said maybe, depending on what he meant by fun.  He suggested we go outside to discuss the situation.  Elaine was hesitant but followed.  To our surprise the guy had a real nice luxury car.

 

     He invited us to go for a ride in his car.  I can't really think of what line he used, but we were young, dumb and horny.  I sat in the front seat with Elaine in between us. She was wearing a short skirt and let him put his hand on her leg.  I wasn't sure where we were going nor what was going to happen, but Elaine told him she felt uncomfortable.  He assured her he was not going to do anything she did not like.  He just wanted to touch her a little and watch us fuck.

 

   We finally found a secluded place to park behind some closed store building that had security lights.  He situated the car where the light shone into the window enough to let him see what was going on.  I could tell Elaine was still somewhat nervous and I said we would leave whenever she wanted and the driver agreed.  While still sitting between us Elaine reached down and slid off her panties leaving her pussy somewhat revealed.  At this point in our relationship she had never taken things this far.  We were not married, but I was living with her.  She let me take photos of her and we engaged in sex talk about introducing others into our sex lives, but talk was as far as we had gone. I was almost as nervous as she appeared to be, but anxious to see where this evening was going to end.

 

   She leaned over and kissed me leaving her ass and pussy @@@@@@@ to the driver.  He slowly massaged her ass as I continued making out with Elaine like a teenager.  I started feeling her up and he finally got the courage to move is hand to her pussy.  I thought she might object but she let him play with her cunt as I played with her tits. She reached down and unbuckled my pants, pulling out my cock.  After fondling me for awhile she repositioned herself on her knees, sideways in the front seat with her head and mouth on my cock and her pussy @@@@@@@ to the driver.  He started playing with her ass again gently massaging her butt cheeks.  It looked like he slid a finger inside her.  I thought she might object but she just kept sucking me letting him have full access to her pussy.  He got braver using both hands, slowly spreading her cheeks and licking her pussy.  I thought maybe we were going to experience our first MMF sex intercourse.

 

   Elaine instead moved over and sat on top of me facing the front and lowered her pussy onto my cock.  I had pulled her top up over her boobs and she left them @@@@@@@ while grinding on me.  The driver moved closer to us and reached for Elaine's tit.  She didn't object, but did tell him all he could do was touch.  He said fine, but could he touch himself.  Elaine said okay but he was not going to screw her.  Surprisingly he did not seem to care.  I was curious how this was going to end.

 

   After playing with her boobs he slowly moved his hand toward her crotch and I wondered what was going to happen next.  We had been screwing with my legs apart and her leg somewhat together kind of doggy style while sitting in a car seat.  She told the driver to wait a minute and I thought the party may be ending.  Instead she got off me momentarily, pushed my legs together the placed her legs outside of mine and sat back on my cock.  Then Elaine took his hand and guided it to her crotch.  It was kind of weird but she seemed to enjoy the extra stimulation of him fingering her clit and pussy lips as my cock was in her at the same time.  I could kind of feel him manipulating her pussy lips but she just continued grinding on my dick.  After a few minutes Elaine said it was time to switch and I thought she was going to fuck the driver.

 

   Instead she turned around facing me and straddling my cock with her knees bent under her.  The driver was playing with her boobs and pulling his own cock.  I guess she felt sorry for him because she leaned back and pulled his face to her tits allowing him to kiss her nipples.  With this action she started cumming hard causing me to shoot off inside her warm pussy.  When I finished I glanced over to the driver and he had shot off and was cleaning himself with a hankie.  I kind of felt sorry for him, but all he could do was thank us and tell Elaine how pretty and sexy she was. 

 

   I knew then I had a special lady.  We all got dressed and he drove us back to the bookstore.  Never saw him again.  Certainly not the wildest sex story, but memorable to me because it was the first time Elaine had allowed another man to play with her while we were fucking.

  

The irony of the encounter at the bookstore was that it almost backfired for me and my plans for Elaine and future fun.  She admitted she actually enjoyed the sex but not the atmosphere at the bookstore.  While it was erotic it was also scary for her.  The gentleman in the car told us he was there on Saturday night it we wanted to meet again, but we never did.  It was her refusal to return there that cause me to come up with another angle.    I had to find a guy she felt comfortable and in a setting she liked.  

   I was at a business seminar and met a guy through a mutual friend. His name was Eric .We all went our for happy hour drinks and I got him aside and asked him if he wanted to have some fun with my girlfriend. I showed him a polaroid photo of her and explained that I wanted to watch her get fucked and participate at the same time.  He was willing and I set up at meet for the following night after our seminar.

   When I told Elaine she started getting nervous about how to actually do this as she had never actually screwed more that one man at the same time.  I suggested her meeting him at the door in lingerie, but that was way to aggressive for her.  Since she had never met him we agreed we would invite him over for drinks and munchies.  If she liked him and was willing to try she would invite him to the bedroom.  She wanted to start alone with him and see how things went.  I told her after some kissing and fondling she should know if it was going to work.  If she wanted to back out I suggested she give him a blowjob to completion as a reward for coming over and trying.  If she wanted to go through with complete sex she would signal or invite me in the bedroom.

   Elaine wore garters and hose, no panties, under a front button summer dress.  Everybody seemed to get along when he arrived.  Elaine seemed hesitant to ask him to the bedroom. Eric excused himself to use the bathroom and I checked with her to see if she was still up for it and she said yes but just did not know how to bring up the subject. When he came back I simply asked him if he would like to take my lovely girl to bed.  He said sure and off they went leaving me nervous and hoping for the best.  They left the door partially open and I could hear idle chit chat for a couple of minutes, then the talking stopped.  After several more minutes I slowly opened the door to see Elaine on her back and Eric's head buried under her dress. She smiled and waved me in and the party started.

 

   When I walked in the room I got on the bed and started kissing and playing with her boobs while Eric was eating her pussy.  We were all still dressed so I started getting undressed.  Elaine took off her dress, sat on the edge of the bed and unbuckled Eric's pants, pulled down his underwear and started sucking him.  It was quite a turn on for me.  I sat back enjoying the show.  Pretty soon Eric grabbed Elaine's head and began face fucking her mouth.  She obliged and kept sucking.  Eric warned her he was going to cum if she did not stop.  Elaine grabbed his ass cheeks and held on as he shot off in her mouth.  She swallowed almost all of his cum.  He pulled out of her mouth and collapsed on the bed.  What a way to start our first MMF encounter.  When he went to get a drink or use the bathroom I asked Elaine if she wanted to continue or had she just sucked him off to get him to leave.  She smiled and said she had not been fucked yet and definitely wanted to keep going.

  

   When he came back I was screwing Elaine missionary style.  He watched for awhile as he laid on the bed.  I finally got off her and moved behind her doggy style laying on our sides.  Eric positioned himself so she could blow him some more.  When he got hard again I got out of her and let him have her.  She got on her knees and Eric started screwing her from behind.  I moved in front and let her suck me.  It was my dream come true watching Eric fuck her as she was blowing me. As you probably know f it is really a bit difficult to have a woman give a good blowjob and properly fuck at the same time so we mostly alternated fucking her. 

 

   Keeping in mind she was 29 or 30 and we all had a lot of sexual energy we kept busy sucking and fucking until all were satiated.  He thanked us profusely and left. We collapsed in bed asleep.  In the morning  I was afraid she would feel guilty and say never again.  I asked her what she thought about everything that happened.  She asked me if I had a good time.  I assured her I had and she said great.  I asked would she do it again and she said probably but it would have to our special secret and we must be discreet

   I did not take any photos, but later got her to wear the same garters and dress.  We got to talking about how much fun we had.  She started playing with herself for me and we ended up screwing on the floor.  Hope you enjoy our little adventures.

 

The white skirt and black top are what she wore to the bookstore and the other pics are what she wore to meet Eric

 

Totally hot story.  Thank you!  Too bad the pics don't show.

[robert smith]

16 hours ago, cucksean said:

Just go to Elaine's First Time thread in the Cuckold Stores forum and you will find many stories and 100s of photos

 

[cucksean]

1 minute ago, robert smith said:

 

Yes sir!  I have been reading!  So hot

[robert smith]

[cucksean]

3 minutes ago, robert smith said:

Is that your favorite?

[robert smith]

I have too many pics to call one my favorite.  What is your favorite?

[robert smith]

Here are the photos to go with the 2 stories Cucksean posted earlier

[cucksean]

1 hour ago, robert smith said:

Here are the photos to go with the 2 stories Cucksean posted earlier

So lucky and such a beautiful hotwife

[robert smith]

First time she let me take pics of her fucking another man

[cucksean]

38 minutes ago, robert smith said:

First time she let me take pics of her fucking another man

So beautiful Robert

[robert smith]

[robert smith]

[cucksean]

3 hours ago, robert smith said:

Wow beautiful!  Thanks Robert

[robert smith]

 

 

[ritter2bill]

On 6/19/2015 at 8:36 AM, robert smith said:

Here is Elaine at 30 in the very bedroom we experienced our first threesome with Eric

Gorgeous Woman!

[ritter2bill]

On 7/24/2022 at 11:04 AM, robert smith said:

I have too many pics to call one my favorite.  What is your favorite?

All - She is so gorgeous!!!

[cucksean]

[cucksean]

Just now, cucksean said:

That is just one of my fav

[robert smith]

[robert smith]

[cucksean]

18 minutes ago, robert smith said:

Omg I wish my bride would try that!!

[robert smith]

It took nearly 20 years to convince my wife to fuck her first BBC.  What a great memory.  Here is part of that story

  Elaine's cocksucking skills got his dick hard and soon he was reaching for a condom.  His cock was about the same length as mine, but his girth was impressive.  After he wrapped up Elaine smiled at me and said  "I can't believe I am doing this.  My mother would die".  We all chuckled and Nate sat on the couch as Elaine backed up and lowered her pussy onto his cock.  She went down slowly saying she wasn't sure she had ever fucked a guy quite that wide.  I had a perfect view of her pussy as she reached down to pull her pussy lips apart as she sat on his big cock.  Soon she was taking it all in and grinding as Nate was reaching around tweaking her tits.  What a sight!  Nate's black hands covering her boobs as his big black cock was lodged between her creamy white thighs disappearing into her pink pussy.  She motioned me over and told me to kiss her.  She whispered "Do you still love me?".  I said more than ever and she smiled.  She unzipped my slacks and the party really got going. 

 

[robert smith]