Sex Cheating true stories blog

First Time

by cuckolder

08/21/2016 12:26 in cheating


My wife and I have been married for a long time. We are deeply in love, and have a great sex life. I have always been kinkier than her, but over the years she has explored with me and over time become a sexy minx who secretly loves our kinky play. She is very beautiful, slim, erotic and with a body that make me proud to be her husband.

I have always had bi fantasies, but like most guys have kept those thoughts hidden and locked away, other than a near encounter when at University I have never told anyone about my bi fantasies.

As my wife started to open up to kinky play I explained to her my bi fantasies, at first I think she was shocked but over time, she started to accept my fantasies and we played with them, enjoying occasional strap on and anal play.

I had just about given up the idea of actually experiencing play with another man, when one day my wife suggested that perhaps we should find a male submissive to play with us both.

I placed an advert online, "Femdom couple looking for a submissive man to join us - must be 6' tall, athletic and well hung".

Over the next few weeks we received several offers but one guy stood out. He was mid twenties (we are mid forties), 6'2" athletic with a six pack and hung. I mean I am OK, at 6.5" but he must have been closer to 8". We both loved his pic and after a few emails and a Skype chat we decided to go for it. During the Skype chats she never showed her face to him.

Our biggest concern was safety, what about STD's, what about physical safety, so my wife came up with an ingenious idea!

We contacted 'Josh" and told him that as long as he followed our instructions to the letter he would have the night of his life! Luckily he agreed.

My wife chatted to him several times on the phone, on a few occasions she even masturbated for him on Skype as I was forced to watch. About a month before our planned meeting she told Josh to order a CB Curve chastity device. One week before the meeting she ordered him to put it on, and use a numbered tag, this he did and on Skype showed her that he was securely locked up. At the same time she put on my CB Curve and locked me up.

Over the course of the next week she had me give her oral pleasure every day whilst Josh watched, needless to say we were both very worked up by the time our planned meet came around on the Saturday.

She had decided that we should meet at an amazing dungeon that we had once played at, it a was a few hours' drive from our home, so off we set. On arrival at the dungeon the proprietor showed us around and them left us alone.

I then drove to a local pub where we had arranged to meet Josh. When I entered I saw him at the bar, I approached said hello and bought him a drink. He asked where my wife was and I told him she was waiting nearby, of course he was suspicious, but I called her and he chatted on the phone with her, and saw her on Facetime. Josh then passed the phone to me with a smile, and she gave me the instructions to check he was still wearing the chastity belt and if he was to bring him back. I told Josh, that I had to check, so we entered the men's toilet and entered a stall, he dropped his trousers and I could see the CB Curve was still in place with the correct numbered tag, so we headed out to the car and drove back to my wife at the dungeon!

When we arrived we entered the foyer of the lounge and found a note from my wife, it read - 'only enter when naked and only wearing your chastity devices' - we both eagerly stripped and then entered the dungeon. There we were, two men, both naked apart from chastity cages walking into a dungeon. What met us was an absolute vision. My wife was seated in a throne, wearing her finest Agent Provocateur Lingerie and an amazing Latex hood, I realise then how clever she was, here we were naked in chastity cages and no one could see her face!

She ordered us to kneel at her feet and we complied immediately, she rose slowly and circled us, running her hand over our shoulders as she explained the rules. We were to do exactly as she said, any hesitation would be met with swift punishment, we were here to please her, not ourselves and we should do exactly as says!

She ordered me to tie Josh to the St Andrews cross. Once he was secure she told me to lay down and place my head in the queening box, this I did and she lowered her beautiful pussy over my face. I began to use my tongue to tease and probe her delicate flower as she watched Josh squirming on the Cross!

After a while I could tell she was getting excited, her pussy juices were running down my face, she had her first orgasm and then lifted herself of the queening box and pulled me out.

She attached a collar and leash to my neck and brought me over to the St Andrews Cross. She whispered her commands into my ear. The shock literally made me blush.

She went and sat on a chair near the bed and took out her Hitachi wand and started pleasing herself as she watched me carry out her instructions.

First I attached a collar with a back strap to Josh, then cuffs to each wrist. One by one I attached Josh's wrists to his back, and once his hands were secure I released his feet. I attached a leash to his collar and locked his collar shut with a padlock which had no key. I then led him to the bed, all the while my cock was straining against the chastity device and I could see his was as well. We were both transfixed watching my wife in her beautiful lingerie using the wand against her swollen pussy lips.

Once on the bed I attached his arms to the headboard and he lay on his back, then I opened the drawer at he side of the bed and there was a small pair of scissors and I carefully cut the tag to his chastity device and watched in admiration as he swelled. He had been in there for over a week, and it was obvious he was desperate to cum.

I took a face cloth and cleaned his cock, it was the first time I had ever touched another man's penis and as my wife watched a million different thoughts flooded my brain.

Once cleaned as per my wife's instructions I started to stoke his body and use my mouth to kiss and lick his nipples, gradually his cock hardened to its full size and then I took a spray can of desensitising spray and applied a liberal layer to his fully grown impressive manhood.

First I put on the extra safe condom, then my wife got off her chair, came over and guided my head to his cock. It was inches from my face as she whispered into my ear, "take it, take him in your mouth". My lips circled his head, and gradually let him slip into my mouth. All the time my wife had her hand on my head and she kept whispering encouragement and pushing my head further down. I felt her behind me playing with my ass, first one finger then two, then gradually I felt one of our butt plugs pop into my ass.

After what seemed forever she pulled my head back by my hair and told me to get her the latex sheath. This I did and I pulled it onto Josh, so now his desensitised ex caged cock was completely upright and looking bigger than ever.

My wife straddled him and ordered me to hold his cock and watch closely as she lowered herself onto his proud member. Gradually with each bounce she took a bit more of him, and I watched transfixed as inches from my face my wife rode with wild abandon this great cock. Poor Josh, between the spray, the condom and the latex sheath he probably couldn't feel a thing!

She ordered me up and told me where the key was to my chastity cage, you have never seen a man remove a cage so quickly. Once my cock was free my hand instantly went to it, but a scolding look told me that it was her cock and I was not to play with it. Instead she had me fondle and kiss her breasts and mouth as she rode Josh.

As she got close to her second or was it third orgasm she ordered me to get behind her and kiss her sweet ass, and as I did that I was to get myself hard and put on a condom. I was so happy, kissing her ass was one of my favourite pastimes, yet now I also got the pleasure of kissing her ass as she rode this latex clad monster of a cock. She had entered her multi orgasmic phase so she leant forward and grasped Josh's body as he now bucked up desperately trying to feel something, yet his mind must have been exploding, his head rising to kiss and lick her beautiful boobs.

Gradually I took my now hard penis an slowly started to push it into her ass. She stopped rocking and gradually allowed herself to open up and take both our cocks. I could feel how large his cock was in her now stretched pussy.

This carried on as she experienced wave after wave of orgasm, just before she was exhausted she got of Josh and told me to lie next to him. She pulled off my condom and lowered herself onto me. The feeling was so intense that I knew I wouldn't last, but she is an expert. She held herself with just my head inside her and ordered me not to move. I was so tempted to thrust, to claim my orgasm and my wife, however the submissive in me won, and I stayed still as she ruined my orgasm into her well fucked hot pussy. The frustration was torture, my hard on hardly subsided I was in sub bliss and kink heaven. She slowly rose from me and then moved up my body and sat on my face, forcing me to eat my own cum. The taste was something I had never got used to, not unpleasant but wrong, it turned me on and disgusted me at the same time. All the time this was going on she was looking at Josh, and she had removed his latex sheath and condom. His cock was so swollen it almost looked painful.

By this point my wife had had several orgasms and was exhausted, she slipped out her lingerie and put on a silk robe.

She attached a length of chain to Josh's collar and padlocked it to the bed, she then told me to dress in her lingerie and put on an identical latex mask as hers. She sprayed me in her perfume, and had heels for me in exactly the same style as hers. As I put on her stockings I know realised why she had insisted that morning that I shave all of my body hair off. Josh was grinning from ear to ear as he realised what was about to happen. With the chain around his neck securely padlocked she ordered me to release his hands. It was like releasing a caged animal. Here was a man, who hadn't cum in weeks, been teased for hours by a lingerie clad beauty in a latex hood, and now just out of reach was that woman, but in his reach was her husband, smooth, in her lingerie and smelling just like her.

She ordered me to put a fresh condom on Josh and do as he say.

Josh pulled me down to his cock and started to fuck my face, gently at first but then slightly rougher, I heard my wife warn him to not hurt me, after all she still had the keys to his padlock. Josh slowed down a little and realised he was still being controlled. He ordered me on all fours, and got behind me. Here it was, the first time, time for me to lose my bi virginity.

I felt him remove the butt plugs and apply a big dollop of lubricant, I was going to need it. As I felt the tip of his cock push against my virgin ass, my wife came over and kissed me, she whispered in my ear how horny this was to her, that I was helping her, as her pussy and ass had been so thoroughly fucked she couldn't fuck anymore and our guest had to get off. Josh slipped into me, searing pain at first but as my wife directed him, he held it there for a while as I gradually became adjusted to him. Then he started to speed up, all the while she held my head, kissed me and whispered in my ear. The pressure on my prostate was insanely intense and I started to leak cum, I was being milked by his cock. My wife, the forever kinky one was catching my cum with her hand and feeding it to me and then kissing me as we snowballed my cum. Eventually Josh's pace quickened and we knew he was about to cum.

She gave him the choice he could either cum in the condom in me, and then eat it from the condom, cum on my back and clean it off, or cum on her beautiful breasts. He obviously chose the latter, so he pulled out of me, and straining at his leash and chain he tried to pull my wife to him. She scolded him and told him to be patient. I was ordered to cuff his hands behind his back, and the I slowly started wanking him, my wife came closer and his bare cock now touched her skin for the first time. He was bucking wildly and pleading with us to let him have a full orgasm, now painfully aware that if she wanted to, she could order me to ruin his fun.

She smiled sweetly and told him he had been a good guest and he could cum. I pumped him as fast as I could and I felt his orgasm rush from within him, spraying what seemed like gallons of pearly cum onto her beautiful naked breasts. When he was done she presented her breasts to him and he greedily cleaned them, licking up every inch of his cum.

As he collapsed spent, she donned her coat and left the room, leaving just myself and Josh. I untied him, released his chains and then drove him back to our original meeting point. At no point had he been in control, and he had never seen her face, but I was sure it would be a night to remember. As I puled back into our hotel, I walked to meet my wife in the bar, I realised I was the only one who had not had a full orgasm. I was still as horny as hell, and could feel my hardon rising against my wife lingerie that I still wore under my clothes. 
I found my wife at the bar as planned and she smiled, she had a wicked smile. She order her usual, a glass of wine for me, and a vodka tonic. I was surprised as vodka wasn't a drink either of us liked. I asked her who it was for, and just then a stunning brunette joined us and my introduced her as Rachel, a friend she made on the internet, with a wicked grin on her face. It looked like it was going to be a night of many firsts!My wife and I have been married for a long time. We are deeply in love, and have a great sex life. I have always been kinkier than her, but over the years she has explored with me and over time become a sexy minx who secretly loves our kinky play. She is very beautiful, slim, erotic and with a body that make me proud to be her husband.

I have always had bi fantasies, but like most guys have kept those thoughts hidden and locked away, other than a near encounter when at University I have never told anyone about my bi fantasies.

As my wife started to open up to kinky play I explained to her my bi fantasies, at first I think she was shocked but over time, she started to accept my fantasies and we played with them, enjoying occasional strap on and anal play.

I had just about given up the idea of actually experiencing play with another man, when one day my wife suggested that perhaps we should find a male submissive to play with us both.

I placed an advert online, "Femdom couple looking for a submissive man to join us - must be 6' tall, athletic and well hung".

Over the next few weeks we received several offers but one guy stood out. He was mid twenties (we are mid forties), 6'2" athletic with a six pack and hung. I mean I am OK, at 6.5" but he must have been closer to 8". We both loved his pic and after a few emails and a Skype chat we decided to go for it. During the Skype chats she never showed her face to him.

Our biggest concern was safety, what about STD's, what about physical safety, so my wife came up with an ingenious idea!

We contacted 'Josh" and told him that as long as he followed our instructions to the letter he would have the night of his life! Luckily he agreed.

My wife chatted to him several times on the phone, on a few occasions she even masturbated for him on Skype as I was forced to watch. About a month before our planned meeting she told Josh to order a CB Curve chastity device. One week before the meeting she ordered him to put it on, and use a numbered tag, this he did and on Skype showed her that he was securely locked up. At the same time she put on my CB Curve and locked me up.

Over the course of the next week she had me give her oral pleasure every day whilst Josh watched, needless to say we were both very worked up by the time our planned meet came around on the Saturday.

She had decided that we should meet at an amazing dungeon that we had once played at, it a was a few hours' drive from our home, so off we set. On arrival at the dungeon the proprietor showed us around and them left us alone.

I then drove to a local pub where we had arranged to meet Josh. When I entered I saw him at the bar, I approached said hello and bought him a drink. He asked where my wife was and I told him she was waiting nearby, of course he was suspicious, but I called her and he chatted on the phone with her, and saw her on Facetime. Josh then passed the phone to me with a smile, and she gave me the instructions to check he was still wearing the chastity belt and if he was to bring him back. I told Josh, that I had to check, so we entered the men's toilet and entered a stall, he dropped his trousers and I could see the CB Curve was still in place with the correct numbered tag, so we headed out to the car and drove back to my wife at the dungeon!

When we arrived we entered the foyer of the lounge and found a note from my wife, it read - 'only enter when naked and only wearing your chastity devices' - we both eagerly stripped and then entered the dungeon. There we were, two men, both naked apart from chastity cages walking into a dungeon. What met us was an absolute vision. My wife was seated in a throne, wearing her finest Agent Provocateur Lingerie and an amazing Latex hood, I realise then how clever she was, here we were naked in chastity cages and no one could see her face!

She ordered us to kneel at her feet and we complied immediately, she rose slowly and circled us, running her hand over our shoulders as she explained the rules. We were to do exactly as she said, any hesitation would be met with swift punishment, we were here to please her, not ourselves and we should do exactly as says!

She ordered me to tie Josh to the St Andrews cross. Once he was secure she told me to lay down and place my head in the queening box, this I did and she lowered her beautiful pussy over my face. I began to use my tongue to tease and probe her delicate flower as she watched Josh squirming on the Cross!

After a while I could tell she was getting excited, her pussy juices were running down my face, she had her first orgasm and then lifted herself of the queening box and pulled me out.

She attached a collar and leash to my neck and brought me over to the St Andrews Cross. She whispered her commands into my ear. The shock literally made me blush.

She went and sat on a chair near the bed and took out her Hitachi wand and started pleasing herself as she watched me carry out her instructions.

First I attached a collar with a back strap to Josh, then cuffs to each wrist. One by one I attached Josh's wrists to his back, and once his hands were secure I released his feet. I attached a leash to his collar and locked his collar shut with a padlock which had no key. I then led him to the bed, all the while my cock was straining against the chastity device and I could see his was as well. We were both transfixed watching my wife in her beautiful lingerie using the wand against her swollen pussy lips.

Once on the bed I attached his arms to the headboard and he lay on his back, then I opened the drawer at he side of the bed and there was a small pair of scissors and I carefully cut the tag to his chastity device and watched in admiration as he swelled. He had been in there for over a week, and it was obvious he was desperate to cum.

I took a face cloth and cleaned his cock, it was the first time I had ever touched another man's penis and as my wife watched a million different thoughts flooded my brain.

Once cleaned as per my wife's instructions I started to stoke his body and use my mouth to kiss and lick his nipples, gradually his cock hardened to its full size and then I took a spray can of desensitising spray and applied a liberal layer to his fully grown impressive manhood.

First I put on the extra safe condom, then my wife got off her chair, came over and guided my head to his cock. It was inches from my face as she whispered into my ear, "take it, take him in your mouth". My lips circled his head, and gradually let him slip into my mouth. All the time my wife had her hand on my head and she kept whispering encouragement and pushing my head further down. I felt her behind me playing with my ass, first one finger then two, then gradually I felt one of our butt plugs pop into my ass.

After what seemed forever she pulled my head back by my hair and told me to get her the latex sheath. This I did and I pulled it onto Josh, so now his desensitised ex caged cock was completely upright and looking bigger than ever.

My wife straddled him and ordered me to hold his cock and watch closely as she lowered herself onto his proud member. Gradually with each bounce she took a bit more of him, and I watched transfixed as inches from my face my wife rode with wild abandon this great cock. Poor Josh, between the spray, the condom and the latex sheath he probably couldn't feel a thing!

She ordered me up and told me where the key was to my chastity cage, you have never seen a man remove a cage so quickly. Once my cock was free my hand instantly went to it, but a scolding look told me that it was her cock and I was not to play with it. Instead she had me fondle and kiss her breasts and mouth as she rode Josh.

As she got close to her second or was it third orgasm she ordered me to get behind her and kiss her sweet ass, and as I did that I was to get myself hard and put on a condom. I was so happy, kissing her ass was one of my favourite pastimes, yet now I also got the pleasure of kissing her ass as she rode this latex clad monster of a cock. She had entered her multi orgasmic phase so she leant forward and grasped Josh's body as he now bucked up desperately trying to feel something, yet his mind must have been exploding, his head rising to kiss and lick her beautiful boobs.

Gradually I took my now hard penis an slowly started to push it into her ass. She stopped rocking and gradually allowed herself to open up and take both our cocks. I could feel how large his cock was in her now stretched pussy.

This carried on as she experienced wave after wave of orgasm, just before she was exhausted she got of Josh and told me to lie next to him. She pulled off my condom and lowered herself onto me. The feeling was so intense that I knew I wouldn't last, but she is an expert. She held herself with just my head inside her and ordered me not to move. I was so tempted to thrust, to claim my orgasm and my wife, however the submissive in me won, and I stayed still as she ruined my orgasm into her well fucked hot pussy. The frustration was torture, my hard on hardly subsided I was in sub bliss and kink heaven. She slowly rose from me and then moved up my body and sat on my face, forcing me to eat my own cum. The taste was something I had never got used to, not unpleasant but wrong, it turned me on and disgusted me at the same time. All the time this was going on she was looking at Josh, and she had removed his latex sheath and condom. His cock was so swollen it almost looked painful.

By this point my wife had had several orgasms and was exhausted, she slipped out her lingerie and put on a silk robe.

She attached a length of chain to Josh's collar and padlocked it to the bed, she then told me to dress in her lingerie and put on an identical latex mask as hers. She sprayed me in her perfume, and had heels for me in exactly the same style as hers. As I put on her stockings I know realised why she had insisted that morning that I shave all of my body hair off. Josh was grinning from ear to ear as he realised what was about to happen. With the chain around his neck securely padlocked she ordered me to release his hands. It was like releasing a caged animal. Here was a man, who hadn't cum in weeks, been teased for hours by a lingerie clad beauty in a latex hood, and now just out of reach was that woman, but in his reach was her husband, smooth, in her lingerie and smelling just like her.

She ordered me to put a fresh condom on Josh and do as he say.

Josh pulled me down to his cock and started to fuck my face, gently at first but then slightly rougher, I heard my wife warn him to not hurt me, after all she still had the keys to his padlock. Josh slowed down a little and realised he was still being controlled. He ordered me on all fours, and got behind me. Here it was, the first time, time for me to lose my bi virginity.

I felt him remove the butt plugs and apply a big dollop of lubricant, I was going to need it. As I felt the tip of his cock push against my virgin ass, my wife came over and kissed me, she whispered in my ear how horny this was to her, that I was helping her, as her pussy and ass had been so thoroughly fucked she couldn't fuck anymore and our guest had to get off. Josh slipped into me, searing pain at first but as my wife directed him, he held it there for a while as I gradually became adjusted to him. Then he started to speed up, all the while she held my head, kissed me and whispered in my ear. The pressure on my prostate was insanely intense and I started to leak cum, I was being milked by his cock. My wife, the forever kinky one was catching my cum with her hand and feeding it to me and then kissing me as we snowballed my cum. Eventually Josh's pace quickened and we knew he was about to cum.

She gave him the choice he could either cum in the condom in me, and then eat it from the condom, cum on my back and clean it off, or cum on her beautiful breasts. He obviously chose the latter, so he pulled out of me, and straining at his leash and chain he tried to pull my wife to him. She scolded him and told him to be patient. I was ordered to cuff his hands behind his back, and the I slowly started wanking him, my wife came closer and his bare cock now touched her skin for the first time. He was bucking wildly and pleading with us to let him have a full orgasm, now painfully aware that if she wanted to, she could order me to ruin his fun.

She smiled sweetly and told him he had been a good guest and he could cum. I pumped him as fast as I could and I felt his orgasm rush from within him, spraying what seemed like gallons of pearly cum onto her beautiful naked breasts. When he was done she presented her breasts to him and he greedily cleaned them, licking up every inch of his cum.

As he collapsed spent, she donned her coat and left the room, leaving just myself and Josh. I untied him, released his chains and then drove him back to our original meeting point. At no point had he been in control, and he had never seen her face, but I was sure it would be a night to remember. As I puled back into our hotel, I walked to meet my wife in the bar, I realised I was the only one who had not had a full orgasm. I was still as horny as hell, and could feel my hardon rising against my wife lingerie that I still wore under my clothes. 
I found my wife at the bar as planned and she smiled, she had a wicked smile. She order her usual, a glass of wine for me, and a vodka tonic. I was surprised as vodka wasn't a drink either of us liked. I asked her who it was for, and just then a stunning brunette joined us and my introduced her as Rachel, a friend she made on the internet, with a wicked grin on her face. It looked like it was going to be a night of many firsts!


sex free talk first time