Who was wifes 1st? How did it happen?

My wife’s first two experiences were with male coworkers. When we started this journey, she made it clear she needed to know them and needed to feel comfortable with them before playing. This made fucking a stranger difficult. Fortunately, she went out for drinks on a regular basis with coworkers. She picked her target and after some alcohol was consumed, opened the door for free play. The first guy was a bit of a swing and miss due to too much. Alcohol. However, the second guy officially took her hotwife cherry.

She has since gotten more comfortable meeting people online and fucking them too. :cool:
 
I told my wife this fantasy and a few months later we started this journey. I have never picked a lover for my wife, she is the one having sex, so she gets to pick.

I became a cuckold on my birthday. She was with him while I was at work and she told me that night at dinner. She was meeting and playing Pokémon Go with a man, and after I told her the fantasy, she started looking at him in a different way. Once she decided it was going to be him, it was close to my birthday, so she waited for that day. She went to met him as usual for Pokémon Go but she was dressed up. He asked her why and she told him of my fantasy and she wanted him to be the one. So they went to his place and I became a cuckold.
 
Years ago at a party. She was flirting with a guy and I saw them go upstairs. I did not follow. About 15 minutes later he came down and winked at one of his friends. 10 minutes later she appeared and came over to me and hugged me and asked if I was having a good time. I said "Yes". She smiled and has ruled since.
 
Here's my story of our first time:

 
The truth is that I have no idea who the first guy was who fucked Lynn after we got together. When we started dating she was still married to her first husband but screwing around behind his back. That continued after we got together and I had no idea at that time who most of the guys were. Just casual pick ups for the most part. But I loved knowing that she was putting herself about so freely and that lots of guys I would never meet were getting their dicks in my gf.
James
 
First guy she ever fucked after we got together was unplanned I believed. I don't remember his name. Mary, myself, Mary's friend Maureen and her bf of the month , let's just call him Guy. Maureen and Guy are new enough they are still in the use a condom stage of their relationship.

Weekend trip out of state for a concert, 4 money strapped college students, stayed in same hotel room, two queen beds. Obviously young, horny, a little smoke, drink neither couple batted an eye at fucking in the same room.

2nd night there after the concert, buzzed, full of energy, each couple fucks. Girls run to the bathroom after. Lots of giggling as they ********, clean up, they yell out to us to turn off the lights. They were still naked, we do. The girls somehow manage to get in the wrong beds....it was not that dark....they had hatched a plan in the bathroom.

Seems guy liked getting head, but would not go down on Maureen, Maureen had noticed the gusto with which I went down on Mary. For Mary's part , Guy was French Canadian, nice accent, and well he had a fat cock, not long but girthy, so she wanted to feel him in her.

Like I said Maureen and Guy were still in the condom stage, she was a former high school cheerleader , with a great rack and big puffy nipples Bf a perfect looking jet black bush. Nobody said s word when the girls made their mistake except for the girls saying oops.

Great night had by all. Though next morning Guy was not as cool with it as everyone else. Seems he was upset at how much Maureen enjoyed herself, never mind that he and Mary had also, they ended up broken up within 3 days.

In truth for as much as I enjoyed Maureen , seeing abd hearing Mary was even more so.
 
Her first time wasn’t really planned. It was a long time ago so don’t recall the exact details of conversations we had before hand. It was with a very good friend of ours one night after the 3 of us had been partying together at our place and were pretty well along. Don’t remember what was said but he and I ended up pulling her down onto the living room floor and just started making out with her. We ended up moving to our bedroom where we spent the night. It wasn’t an all night sex fest but we had fun. Next morning was a bit awkward for me but it was all good.
They ended up getting together two more separate times, once the 3 of us on a remote lake shore after a long canoe ride and the last time with him he had been at our place partying again but left for his place a mile up the road. I sent her to go visit him while I stayed home with our kid at the time. Both those times involved some partying too.
 
Hmm, that’s a tough question to answer. The reason I say that is because I had given her the green light to do whatever she wanted and with whoever she wanted to, at the very early stages of our relationship. She wasn’t exactly flaunting it, nor was she being openly honest about whatever it was that she would do, but at the same time, she wasn’t trying to be super sneaky either. We had more of a “don’t ask, don’t tell” kind of thing between us. It wasn’t too difficult to figure out that she was, and most often, who she was messing around with, but she wouldn’t just come right out and say it. The one topic that did come up and was fueled by me because it was always one of my all time top fantasies, was about her being with a black guy. She was raised by her parents and her ex husbands that was wrong and so she just said she never really thought about it. Now I’m a firm believer that a lot of women say that but the truth lies hidden deep down inside them, and that the majority of them have been curious or have at least thought about it, but can’t just outright admit it! Little by little I got her to be comfortable enough to tell me if she thought a certain black guy was good looking. I kept chiseling away more and more and eventually got her to the point where she said if it was the right guy at the right time and place, that she would definitely consider being with a black guy. It helped that almost every time we went out, she would get hit on by handsome good looking black men! Fast forward a little and I reconnected with an old buddy of mine from HS, and that he ended up being our main drug dealer! As she became more and more comfortable with him, and then you include that he started hanging out and partying with us and hooking us up with drugs and alcohol, and we were all three getting wasted together, it was only a matter of time before I knew she would give in and let herself go!! I had told him what I was wanting and he made it perfectly clear to me what he was also wanting so it was just a matter of getting Robin to meet us in the middle!! So him and I came up with a plan for me to allow him to have some time alone with just her every now and then, and that would give him time to make his moves and for her to be more receptive to them since I wasn’t right there, and... IT WORKED!! Well actually the first time she ever let herself go was on his birthday. I had told him how amazing she was at giving lap dances and convinced her to give him one for his birthday, and she was more than happy to agree!! She loved giving lap dances!! I told her to go put on this one particular outfit that I loved and that I’d get her favorite music playlist ready. She quickly took off down the hall to the bedroom, and I set up a chair in the center of the room for him to sit in and got her music ready! Her favorite song to dance to is, “you can leave your hat on”! She came back and it was clearly obvious she was very excited and feeling sexy!! I’m certain the party favors helped play a large role in that! I started the music and she started her show!! She would straddle him and ride against his lap and then turn around and bump and grind into his lap, it was awesome to watch!! After a little while the chair began to be more of a problem so I told him to go over and sit in the middle of the couch. He sat down and I told her to sit on his lap while facing him and to lift herself up so her tits were right in his face! The couch was up against a wall so she put her hands on the wall and slowly moved her way up. I told him that she could cum just from playing with her right nipple and told her to lift her thin top up and let him at least touch and lick her tits! She was enjoying the attention so much that she didn’t hesitate and put her bare tits directly to his mouth!! At this point she was almost standing straight up in front of him and I told her she should raise up so her pussy was in his face. Almost as soon as I said that the music stopped and she appeared to like snap out of the groove she was enveloped in and got down from the position she was in and moved over to the loveseat, only two or three feet away and sat down. Throughout this whole time I was sitting in my recliner which is directly across from the couch, maybe about six feet away, and the loveseat was right next to my recliner.
——— = the couch
| = the loveseat
— = my recliner
That’s the best diagram I can do. Lol. He was quick to make the comment that he was so close to cumming just before she stopped! I told her to keep giving him a lap dance until she made him cum, which she’s done several times before out in the club. She said she wasn’t sure she could do that, to which he spoke up and said that if she would just give him a quick handjob, that he would cum within a matter of seconds! She told him she didn’t think she could go through with it and do it. She then spoke up and said that she would watch him masterbate if he thought that might help! He was just kind of going back and forth and from what I could tell, was trying to figure out a way to get her involved and was stalling, as him and I both were trying to talk her into thinking about other ideas. I was of the mindset that if she would start doing one thing, that she would most likely take it even further, but it had to start out as something minor! She again said that she would watch him but that was it. He said that he didn’t know if he could do that, with me right there watching. Lol. I laughed and told him that I had no interest in watching him and that I would just leave the room for a little while. Now the important thing to know about Robin is that she was always very sneaky and he knew that as much as I did! So I already knew what he was going to try to do and to see how far she will really go if I’m not in the room! I told them I would just go to the bathroom down the hallway. But before I left I took notice of how everything looked! I noticed that he was sitting almost directly in the middle of the couch and that she was sitting almost in the middle of the loveseat and that there was a pillow up against the armrest of the loveseat closest to the couch. I got up and headed down the hallway and just before I went into the bathroom I looked back to the room they were in and because of where the loveseat was and where she was sitting, I could see the top of her blonde hair and that she was sitting straight up, and then I closed the door behind me. I had to take a ******** and once I was done, I put my ear up against the bathroom door and the walls trying to see if I could hear anything! I could hear some sort of noise and could them talking, but it almost as if they were whispering. At one point, I shut off the lights and quietly opened the door and stuck my head out to look down the hall. The only part that stood out to me was that I couldn’t see the top of Robin’s head! I was getting hard just playing different situations that might be going on! I waited a while and then decided to come out and so I made sure that I made plenty of noise so they would know that I was coming. I was hoping that if anything was happening that they would just have kept on going as I walked in! As I entered the room the first thing I noticed was that my buddy wasn’t sitting in the same spot and that he was now moved just a little bit over and closer to the loveseat! But the main thing that I noticed was after I sat back in my recliner, I noticed that Robin had on her guilty face!!! She was horrible at lying and had a terrible poker face!! Then I noticed that she was no longer sitting straight up but was now leaning her whole body towards the armrest closest to the couch and that the pillow was on the other side of her!!! She had almost completely changed positions on the loveseat!!! One last thing was that her hair didn’t look quite right, I didn’t pay attention to it beforehand but it just looked off!! I didn’t say or bring anything up other than I asked if he did it or not. He said no and that he couldn’t do it by himself and so I looked at her and told her that there has to be something she could do to help him! I even suggested that what if he wore a condom, then her hand wouldn’t technically be touching him!! I couldn’t help but notice that by this time she seemed a little more excited. So I suggested that she should go over and sit right next to him so she could get a close up look and that with her being that close to him, it might be more exciting for him! And that she could run her hands and fingers up and down his thighs! I could tell by the look on her face, that she was perfectly fine with that idea and moved over and sat next to him! More to come...
 
Question: Who did you let your wife fuck the first time?
Answer: I didn't let her. She made the decision and told me it was going to happen.

Here are the details in a link to my first post. https://www.wifewantstoplay.com/threads/question-for-sissy-cucks.24199/page-4#post-631617

Question: How did it actually happen?

Answer: The story in the link tells how.

Question: Was is a plan or just something that was not planned at all?

Answer: Oh, she definitely planned it.
 
Ours was planned out months in advance. I interviewed a few prospective black men to fuck her. I think on the 3rd I found someone who fit the bill. Then we met him a few times for coffee or dinner to feel things out. Both got tested during this period. then when she was reluctantly ready, we scheduled a hotel room. He fucked her. Details posted elseware. Then we decompressed for a month or so. Then she hit it hard for A year. Best sexual time of our lives.