How did you get into cuckholding?

My first time was totally impromptu when I was 18. My girlfriend and my best friend and I were drinking at my parent's house one night. My parents were out of town. As we drank and hung out, I started feeling horny...I was always horny at 18. I started kissing my girlfriend and feeling her up. I noticed that y buddy was watching us. The three of us had known each other since 8th grade.

I started to pull my girlfriend's top off, and even though she was braless, she let me. My buddy was seeing my hot girlfriend's tits for the first time. His eyes were bulging out LOL. I kept kissing my girlfriend and feeling her up in front of my friend. He was just openly staring at us now. I knew that my girlfriend really liked sex but we had never discussed adding anyone to our sex fun./

Having no idea how she might react, I whispered into her ear that it was unfortunate that my buddy had to just-watch. My girlfriend got up and went over to my buddy and started kissing him. Now I was watching him play with my girlfriend's tits. it really turned me on. My girlfriend had my buddy stand up. She pushed his pants down and started sucking his cock, That was so hot.

I went behind her and helped her out of her pants. She laid back and pulled my buddy down between her open legs. I watched my buddy slide his bare cock into her and start fucking her. He only lasted about 10 minutes before he came in her. My buddy seemed embarrassed about fucking my girlfriend in front of me and he did not know what to do next, so he pulled up his pants and left.

I went to my girlfriend and started kissing her, even though I knew she had just sucked my friend's cock. I could taste him on her lips and tongue. I slid my hand between her legs and I realized that the extra wetness was my buddy's cum leaking out of her. I slid my cock into her and it was the most incredible thing I had ever experienced. I lasted about 2 minutes.

My girlfriend and I discussed what had happened. I admitted that seeing her with my buddy was exciting. She admitted that having sex with another guy right in front of me turned her on too. I asked her if there were other guys we knew who she might consider having sex with. We talked about a lot of guys but we ended up with a list of six guys.

I got an apartment right away so we could have the required privacy. Over the next few months, we got each of the guys on our list alone and she seduced each of them and had sex with each of them in front of me. Over the next few years, each of those guys had sex with my girlfriend (later my first wife) many times. Three of them continued fuking her even as they dated and married other girls.

I have never been in a monogamous relationship since that first time.
 
I have a question but off topic... why do so many people call it cuckHolding where the hell did the H come from???
 
We got into cuckolding through cheating. Sophie had her first affair while we were engaged but living apart. I found it concerning but also very arousing. After we got married she had sex with a number of guys without telling me (although I suspected). I caught her in the act and she admitted she had fucked others too. My arousal was through the roof! We started swinging but gravitated to hotwifing which we both prefer. However, she still cheats and I do regard this as the high point of cuckold arousal.
 
I have an impregnation/breeding fetish and have been helping women get pregnant for the past 11 years as a sperm donor. I was introduced into the cuckold/hotwife lifestyle by chance 3 years ago when a woman I had agreed to help fall pregnant asked me if her husband could watch and masturbate as I impregnated her, I was shocked but agreed to it and I absolutely loved the experience and decided to explore the lifestyle further.
 
My wife and I had been together for some years and sex became a bit repetitive, so I suggested swinging. This was before the Internet. I bought a relevant magazine and wrote to a couple. We had them round for dinner and had great fun after. The other lady was tall and statuesque and very beautiful. She started on my wife, kissing her and going down on her. My wife laid on the floor with the lady's head between her legs. Her husband quickly undressed and offered his cock to my wife's mouth, which she eagerly sucked. I became spellbound watching her suck another man. So much so, that I forgot to look after the visiting lady that was busy licking my wife. Her husband had to prompt me to get involved.
It wasn't long before he pushed his cock into my wife and she was giving a loud audible grunt on every thrust. Again, I'm spellbound. But I managed to fuck this beautiful lady but I didn't really give her the proper attention she deserved.
It still took me some while to make sense of my feelings, but after more swinging and a recurring situation where I'm watching my wife fucking other men, I started to realise that I would actually be happier just getting men to fuck my wife while watched and joined in.
The first time we did this specifically, I managed to convince my wife that what was I wanted. She was a bit puzzled why I would want to do this (she still is) but after a bit of encouragement said OK. My tactic was to find the right guy. I knew she liked a particular porn video that had a guy fucking two girls around a pool. He had a very thick cocktail and she always got very wet watching but denied it was his thick cock.
Now I've given her a choice of selecting a guy with the right physical attributes. This got her interested. I found this guy, Bob, who certainly had a big cocktail. It was 9" long and almost as thick as a Coke can. I offered this picture of Bob to my wife and she was very interested in his girth. But being so thick didnt reveal the length very well, and 9" was a bit long for her. But she said yes.
I booked a really nice hotel and we both prepared ourselves for the encounter. This was almost the best bit. Her laying in the bath shaving her pushy for him. I masturbated her for a while to help liven things up. She returned the favour when I bathed. Watching her dress up in the obligatory black stockings and underwear did nothing to alleviate my semi erection.
Just the two of us had a lovely dinner in the hotels restaurant and arranged to meet Bob after. By this time I'm getting a dry mouth in anticipation. We agreed to special signals if she didn't want to go ahead or she did want to carry on. Bob arrived, we had a drink at the bar and my wife gave the signal that she was happy to get fucked.
So up to the room and as soon as we got there and closed the door and to alleviate any awkwardness, I decided to break the ice by just lifting my wife's skirt up and revealing her black underwear. I then pulled her knickers to one side and exposed her pussy, parting her lips with my two fingers. I said to Bob, "are you looking forward to fucking this"? He mumbled a quick yes. This really turned us all on, especially me. I knew what my sexual proclivities were now, no doubt.
I then got my wife to go on her knees and release Bob's cock. When it sprang out, I remember her saying "good lord" he was bigger than she realised. I was a bit concerned that she wouldn't be able to accommodate him but that was mixed with sheer excitement that she would be taking such a size.
He took his time with her with a fair bit of foreplay and getting her pussy ready. When he did penetrate her, it was only halfway in to get her used to it but she was struggling. After about 10 minutes of gentle thrusts, she got to the point where he got the whole length in. There were lots of changing positions and more oral until he spooned her with vigorous thrusts until they actually orgasmed together.
I then fucked her soaking pussy to relieve my considerable tension. I think I pumped far more cum than I usually would do, not unsurprisingly. We rested for half an hour and repeated the whole performance.
This first proper cuckolding experience was the best sexual moment of my life, and I knew this lifestyle was for me. My wife could have what she wanted from me here on in.
Thank you for reading. This is a 100% true experience for us.
 
I just enjoy seeing my wife fucked, well it was an ex gf when it started.
a buddy of mine was drunk and hitting on my gf. She said she’d fuck us both if I didn’t mind.
so I said sure.
had a few Mfm 3somes. All fun.
then my buddy asked on night again and I didn’t feel well. I told him if she was ok with it he could fuck her.
She said yes, but it took him some work to get her to.
I watched and I enjoyed it.
I asked him to do it a few more times.
when he was done I’d fuck her and it was the best sex ever!

next gf I dated for a couple months.
mine night my same buddy came over with 2 friends. They were drinking, my now ex was drinking. I told her she could fuck them all. Her and her friend shared them for hours. When they were done, my gf and her friend had a 3some.
When we broke up, I was her bill for months her new bf didn’t like it.
he would get so mad I’d cum in her mouth then she would kiss him.

Then I met my wife. My buddy from before was joking with her about having sex one last time on our wedding day. So I told him to fuck her. He fucker her minutes before the wedding in the church. Then that night him and my other groomsman fucker her before I did. Little fighting there. Both their wife’s where there too. My buddy’s wife was a mad at us. My groomsman’s wife and I fooled around before so she seen it as fair. She actually watched with me. Helps get me extra wound up by telling the guys what to do.
 
I just enjoy seeing my wife fucked, well it was an ex gf when it started.
a buddy of mine was drunk and hitting on my gf. She said she’d fuck us both if I didn’t mind.
so I said sure.
had a few Mfm 3somes. All fun.
then my buddy asked on night again and I didn’t feel well. I told him if she was ok with it he could fuck her.
She said yes, but it took him some work to get her to.
I watched and I enjoyed it.
I asked him to do it a few more times.
when he was done I’d fuck her and it was the best sex ever!

next gf I dated for a couple months.
mine night my same buddy came over with 2 friends. They were drinking, my now ex was drinking. I told her she could fuck them all. Her and her friend shared them for hours. When they were done, my gf and her friend had a 3some.
When we broke up, I was her bill for months her new bf didn’t like it.
he would get so mad I’d cum in her mouth then she would kiss him.

Then I met my wife. My buddy from before was joking with her about having sex one last time on our wedding day. So I told him to fuck her. He fucker her minutes before the wedding in the church. Then that night him and my other groomsman fucker her before I did. Little fighting there. Both their wife’s where there too. My buddy’s wife was a mad at us. My groomsman’s wife and I fooled around before so she seen it as fair. She actually watched with me. Helps get me extra wound up by telling the guys what to do.

Fucking your wife/gf right after some other guy(s) fucked her is the best pussy ever.
 
I think it started for me with one of my first serious girlfriends I was like 18ish. She was definitely hot, but also she was known as kind of a hoe before we started dating and it didn't bother me for some reason... we fucked all the time... eventually there was a night she was out partying with her friends and they ended up at one of my friends house who was a quite a bit older like 25ish. Anyway she was drunk.. flirting im.sure and this buddy of mine ended up fucking her. She comes back home, and tells me she was at this guy's house we both know and apparently he was in a low budget porno this was 20 yrs ago, and he had a huge cock, they all watched it and later she wanted to see it. So she was confessing and saying how many times she came and I started yelling at her calling her a slut when I realized how horny it made me I ripped her clothes off fucked her hard as I could asking if she liked his big cock. Years later I had a gf, who we got drunk as hell one night and started talking about her ex who was like a cage fighter... she left him a VM saying she wanted his cock. She played a few times and recorded it... but wasn't a huge deal. My gorgeous wife now, when I first told her about my fantasies she was mad. Why wouldn't I get jealous, then she found out it was really intense jealousy. And she got super into it. Joined a.Swingers group and have met awesome people. I have played with a couple wives but they quickly realized my attention is on my wife... it has been 3 years and we both love it
 
Anna's first time The story dates back to many years ago, summer 2000, Anna then had just turned 35 but despite the many fantasies about it we had never taken the "big step", we had been in a private room in Turin but at the time of going to the part he hadn't heard of games; for years we had frequented the nudist beaches of France such as Cap d 'Ail, those near Saint Tropez and even some beaches in Liguria where nudists and "textiles" coexisted in harmony, but it was the only transgression even if often when we made love the I was wondering if she wanted to have sex with another man, maybe she seemed okay for the particular moment of the request but never had an exciting opportunity presented itself. Due to the change of job Anna only had one week of vacation and we decided to go to Croatia, we had seen that in Koversada there was a naturist campsite with bungalows, we left and the next morning we were lying naked in the sun together with many other couples and single men, almost all older than us, nothing transgressive and for days we only thought about tanning and dinners in the restaurants of Rovinj. One evening while we were enjoying the warm rays of the sunset I noticed that a man not too far from us was looking very insistently in our direction, I did not say anything to Anna but on the one hand I was flattered that he was observing her, she was lying on her back with knees barely raised and he could enjoy the show; after half an hour he got up and came in our direction holding something in his hands that looked like a drawing pad, he was a grizzled man in his 50s 55 years very tanned and probably there for a long time, he was not handsome but perhaps for the integral tan he definitely had its charm. On his arrival Anna sat up and he introduced himself, he was a German and he wanted to give her the drawing he had just made, a pencil sketch that depicted my naked Anna, it was very cute and Anna accepted it gladly, we had been there for days and we hadn't made friends with anyone so chatting would not have been bad, unfortunately we were struggling a little but we all got along with a rusty English and sometimes misunderstandings created ridiculous situations and Anna laughed and I saw her at ease ... .we were naked in front of a naked stranger too but he was not embarrassed. Time was passing and the sun was about to set so he offered us a drink in his bungalow, we didn't feel like saying no because we liked his company both for the gift just received, Anna slipped a sarong over her naked body and we followed him; a few hundred meters further we arrived at her bungalow, well ordered with the towels spread out on a large balcony; he immediately went to work preparing a generous dose of Coca and Bacardi, we sat on the sofas and began to sip the drink always trying to intervene as best we could, since he had been there for a long time we questioned him on the spot and it was inevitable that the speech ended up on the fact that many naked bodies probably led to sex encounters, it was he who asked if we were there for that and Anna blushed I look at me and then sketched an attempt at an answer that did not come, leaving the doubt about the true intentions but the German knew do and without saying a word he got up and proposed the same to Anna, as soon as she was standing he unfastened her sarong and she was naked in front of him, the scenery had changed, we were no longer on the beach among the people of August 15th .. .we were three happy adults for drinks and stuation; she let himself be directed and when his hands touched her nipples she let go; I also got up and stroked her back to make us both understand that everything was ok and that I was in agreement and he started kissing her first on the neck then came to her mouth and I saw Anna totally enraptured by the situation I saw her open her legs to allow his hand to reach her well-shaved cunt, after a while he laid it on the sofa and started licking it between her thighs, she had always kept her eyes closed and emitted only small moans; I was excited but I did not know what to do I just watched, the scene was all theirs and when I saw his penis enter Anna's mouth it was truly ecstasy, she sucked him as until then I had seen him do only with me and just the his cock was erect properly he spread her legs by bringing his erect member closer to Anna's already wet pussy, it was at that moment that there was a moment of waiting .. Anna opened her eyes and looked at me almost asking me what to do. .. I agreed for the penetration and fundamental, he wore nothing .... I was unable to answer I felt my face on fire and I lacked saliva, it was really happening! another man, a stranger, was about to force the casket! there was no time for her answer he was already inside her and ior I approached my wife almost so as not to make her feel alone in that first time, I took her arms and I could not help but watch the German cock moving inside her making the wet lips of Anna's pussy sway, now the ice was broken, the last barrier had fallen, so she was sure that the spiral was working and asked him to come inside; he did not seem to be in a hurry and continued his ride slowing down and accelerating the pace bringing Anna more and more revved up, squeezed her tits, milked her nipples and often searched for her mouth, she arched her belly to better accommodate his little member bigger than what he had known for years. I don't know how long it lasted it seemed like a slow motion scene but in the end he came, gave some powerful strokes and then stopped and so he stayed for a few seconds unloading all the semen into my wife, I was dazed and Anna looked exhausted but happy; I moved next to them and when she came out I saw a white stream dripping from her red cunt and dripping thick on the floor, he was standing in front of her and Anna gave me a glimpse of what her future as a slut would be ... with her fingers a bit of the semen still on her pussy and brought it to her mouth, she did it looking him in the eyes and repeated the gesture then as if nothing had happened she got up and asked where the bathroom was I accompanied her ... she had me the first of hundreds of gifts that I would receive in the future but I still did not know, he made a bidet and asked me if he should tell him to wear a condom, we tried to change the subject and went out, the magic was over and with one last kiss from Anna and my handshake we went out; only the next day we remembered to have left the drawing at her house but Anna preferred not to look for what had been her lover of the day before, on the contrary we changed the beach and she remained chaste for the two days that remained but the transformation had taken place and upon returning we looked for new horizons on dating sites .... I didn't take long to see other men inside her.
 
We got into cuckolding when one night I mentioned that I enjoyed being sub. My wife looked up what to do with a sub hubby she found cuckolding and chastity. A couple of weeks later we went shopping for my first cage after we purchased it she made me put it on and then we went to lunch. at the end of lunch we were having a few drinks and she put the keys on the table and said I had a choice. She told me she has set up a date with an ex she used to swing with in the afternoon and I could either take the keys now and we go or i leave the keys Either way she was going on the date. I was shocked didn’t know what to do my head was spinning this was the first time I heard she was a swinger and she wanted someone else. Due to being stunned I said and did nothing she said well I gues I have My answer and picked up the. Keys and left
 
For us, it was finding my wife messaging other men on fb, talking about how she wanted to see their cocks, get fucked by them, etc. I remember i was crushed, but for some reason i felt so aroused to see my wife ask other men for their big dicks, even while married to me. This, coupled with rumors of her fucking her ex before our wedding, led me to find out she had been cheating on me. When i caught her, she apologized, and said she tried to remain faithful, but failed, and that we could separate if i wanted, but i told her she could continue seeing them. It wasnt until a few years after until we took the plunge, but everytime we had sex we would talk about it, and we would both cum so hard just being turned on about what had happened.
 
My experience is different than most (I think it is anyway). My first few experiences were with me fucking other guys wives/girlfriends. One of my first experiences was when I was 18. There was a couple in their 30's who were friends of the family and I'd do work around their house for them occasionally. Of course any 18 year old boy is open to anything sexual, and the husband often talked to me (while we were working) about how much his wife loved sex. One day he told me he just couldn't keep up with her and asked if I'd like to fuck her as I was young and could probably give her all she wanted. While I was very nervous about him talking to me, the idea of fucking his very pretty wife took front seat... so I told him hell yes! It wasn't long before I was fucking her while he took pictures. It was not only very fun sexually, but it was powerful looking into his eyes, while I was making his wife cum. I loved the feeling it gave me.

Through the years, I've fucked quite a few wives/girlfriends and it's always a wonderful experience.

About two years ago, I suggested my wife entertain a younger, handsome, more endowed guy than me. After a bit of coaxing she agreed and I found being on the other side of that equation very exciting too. Different, but just as exciting.

I don't get off on humiliation and not interested at all in other men... but seeing a woman (whether his or mine) locked in passion while being serviced by two guys is very, very exciting!

I have been on both sides of that situation too and either way is fine with me. My first wife fucked other guys with my encouragement. When we divorced, while I was looking for another openminded (future) wife, I found two married couples who each liked having extra guys around. I have certainly watched more guy fuck my wife than I have fucked other wives.

What I have learned is that married pussy is the best pussy. Married women have a life. All they want from other men is some cock. There is nothing like fucking another guy's wife or watching some guy fuck my wife.
 
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