The Path of the Ultimate Cuckold Part 1
It all started when I was quite young. I was rare for a 22 year old in that I was already quite wealthy as a property developer, so I didn't have to worry about working every day.
I was at my local Nightspot with a few mates on the lookout for any chance to find a girl. (A 22 year old virgin is pretty sad after all. I had had a few relationships but never manged the home run). It was getting towards the end of the night and I had just stepped out for some air. Looking into a dark corner I heard some soft sobbing. Curious and concerned I approached the source of the sound "Hey who's there" I called quietly, and suddenly I saw the most beautiful eyes shining back at me from the dark, clearly moist with tears. " Hey what's the matter?" I tried in my most non threatening, softest most comforting tone I could manage.
I fucking hate my life!" she replied now suddenly angry at the world.
"come on, I'll get you a drink and you can tell me about it." She perked up a little weather it was the offer of a drink or a sympathetic ear didn't really matter. As I walked her to the bar I finally had the chance to take in the rest of her. She was distinctly under dressed but through her jeans and t-shirt casual dress (odd for a Saturday night out) I could tell she had an amazing figure. I bought us a drink and took her to a dark quiet nook in the club. Very soon she started to open up. her parents had split up and her Dad was no where to be found. As a result her Mum was falling apart and was well on the way to being an alcoholic. It turns out she was only 16 (a month or two off 17,not jail bait but only just not). As a result she didn't want to go home and put up with all the crap that came with her situation.
I had just finished renovating my most recent property and it was fully furnished ready to be let, I had been staying there the last few days just finishing it off and thought hell why not. "Look," I said, " don't thing I am trying it on but you could stay at mine, at least until you get your bearings, no strings no sex nothing like that. What do you think?" I offered. She was stunned at first but then her face cracked into a massive smile and she nodded her agreement. After we finished our drinks I took her for a meal and then back to the house. I showed her to the master bedroom... a double and she turned to me with fear in her eyes and it struck me how that must have looked "Nonononoono.." I protested "I will be in here I!" said showing her the guest room. She visibly relaxed and I said my goodnights.
In the morning I made her some tea and toast, and took it to her in bed, politely knocking on the door I made a play on serving her in bed which she clearly found amusing so I played it up even more. " Today I want you to forget all about your troubles and treat me as your chauffeur and personal servant.
"Lets just go wander round town." she said. and so that's how I ended up on a shopping spree buying her lots of clothes. I even bought her some sexy lingerie. It somehow felt good, even though I still had no expectation of sex or the like. I just enjoyed making her happy. We spent the day shopping like mad and ended at a restaurant where of course I picked up the tab. She had a few glasses of wine or three and being young got tipsy quite fast. Being the knight in shining armour as I saw myself at this point, I took her home and we sat and watched a movie. She snuggled up to me and in her hazy state I am sure she didn't realise that I felt the full advantage of her ample young pert breasts rubbing against me.
I was instantly horny of course, but also very conscious that I could not take advantage of this innocent young girl. as the film came to an end and I saw the possibility to get away from the situation and relieve my tension the way any horny bloke would. She clambered on top of me and whispered, let me thank you. I was ready to stop her when I realised all she meant was a kiss, so I relaxed a little. That was when I felt the top of her thigh pressing into my groin, and as the smooch continued my body betrayed me and I stated humping her leg. It must have been less than a minute of this bliss when my orgasm took me. Sudden, hard and fast. There was no way I could hide it as i grabbed her firmly and thrust against her. as the waves of pleasure receded I heard the most wonderful sound. Like an angel laughing in sheer joy but also mockery.
"So your not such a saint after all." she chuckled, "Dirty little fucker just came in your pants,, didn't you?" I couldn't help it her mocking words and light tone made my heart flutter.
"Y... Yess." I managed to gas, adding, "Your too much for me." I let out a sigh, as I let my ego go along with it. Snickering she drove her thigh into my groin again as she snuggled down on my chest.
" I've never made a man come before." she admitted.
"I bet loads of boys have wanked thinking about you." I offered.
"You think so?"
"I know so. You really are hot, and should learn to use it."
"Will you teach me?" she asked, " And who knows in time maybe you can fuck me." She bit her lip and I could see her words shocked her and embarrassed her but also oddly turned her on to be so brazen.
"Well, you have made a great start."
Ewww its all slimy!" she suddenly shrieked and clambered up. A glob of my spunk has seeped through my pants and was clinging to her bare thigh where her nightshirt had ridden up. She saw me looking and bit her lip again. "You dirty pervert, you like that don't you?"
"ughhn!" was all I could manage
"You getting horny again? she asked.
"That obvious huh?"
"Strip then but stay on the floor. I don't want you getting any ideas."
I didn't need asking twice and my clothes were off in record time. I sat on the floor my legs spread so my cock was laid on the floor and I still couldn't take my eyes of my spunk just clinging to her leg, like it was still a part of my body.
"So what do you want to do?" she asked inching closer and raising the nightshirt and tantalisingly close to revealing her panties.
"May I kiss you leg please?" even to me I sounded pathetic but I didn't care I was desperate.
"OK but just to be sure you don't get any ideas..." She stepped forward offering the leg with cum on but stood on my cock, pinning it to the floor and hooked her other leg over my shoulder. My face was level with the cum and I looked up. I could just see her eyes sparkling down at me, staring with intent interest. I started placing light kisses on her leg around my slime and my cock went into overdrive, I wriggled getting as much movement into my cock as I could and the more I wriggled the more weight she put on me. Soon she had all her weight on me but it wasn't enough and I really had my wank on. I couldn't resist any longer an I was overcome with lust, as I felt my orgasm build I opened my moth and slurped my cum off her leg. "OOOOH! she exclaimed and my cock stated to spasm. I knew she could feel it under her foot and she was giggling like the schoolgirl she was.
Fuck my head was spinning there I was with a schoolgirl standing on my cock as I licked my spunk off her and she was laughing at ... and I loved it. Instead of jumping away she seemed to instinctively know to keep the pressure on, and rather she ground her foot on my cock making the last spurts even more intense. I clung on to her leg and she was reassured that she had the right to grind on me as much as she liked.
"All done wanker?" she chided me. I responded by kissing her leg as far up as I could reach.. about an inch short of her crotch. She stroked my head seemingly to comfort me. "Wow... I guess your right, I am sexy." she said. Not an ounce of sarcasm or irony.
"Ehhm," I cleared my throat, "First lesson." I managed to croak.
"Who for? Me or you?" I hugged her leg and grinned up at her...
"Both! Lets get something to eat." I suggested.
"You could lick up the mess you made." she started laughing hysterically and flounced into the kitchen. I grabbed my T-shirt and cleaned up and followed her.
When we got upstairs at her bedroom door she turned to me, "...... with me, please." I was shocked and so mutely followed. She stripped naked and proved me right, she was perfect, even her bush was trimmed. she climbed int bed and I followed. Having come twice I was not about to get a spontaneous hard-on and I still didn't want to breach the trust we were developing. But I found it easy to just cuddle and comfort her untill we both fell asleep.
The next morning I woke up with her nuzzling at my chest and felt her delicate hand explore my groin. Needless to say instant morning wood. She grinned up at me and said "I've decided.. I... I want you to fuck me." before I could answer she kissed me, "Fuck me, please fuck me" kiss. I returned the kiss and flipped her over laying on top of her and making out. I wriggled around trying for position to get us both comfortable and she opened her legs giving me full access to penetrate. I thrust towards her and my cock head made contact with her pussy and I could tell it was moist. I gave another few short thrusts hoping to find her opening but just like the previous night suddenly and without much warning I exploded.
"urghhhhhh!" she let out in clear frustration
"Oh god I am so sorry, but you caught me unprepared. Oh god. Let me make it up to you"
How?" she snapped
"Anything." I pleaded.
"Go down on me then!" she demanded.
"Uh err but I just came."
"So, its your mess and you licked it up last night... go down and clean me!" She actually sounded angry, but there was still a hint of playfulness in it, and I sensed she was seeing how far she could push me. I suddenly realised I wanted her to push me as far as she wanted, and I would go. I threw off the covers and slid down the bed. I wasn't going to balk at this point and started licking my cum up, It was a little watery having cum twice the night before but there was still lots of it.. I licked it up quickly and set to work licking the cutest wettest most amazing virgin pussy ever created, and she started writhing around obviously enjoying the tonging I was giving her. Seeing her turned on pushed my buttons and I was soon hard again. "all may not be lost," I thought I might still pull this off." As I licked I manoeuvred my cock onto her foot and started humping, hoping she would notice and invite me to try again. But she was lost in her own pleasure grinding on my face. And so we continued for about 20 minutes, until I sensed she was close. she pulled on the back of my head and tensed up, jabbing her foot hard into my balls she was Cumming ... and so was I.
As she recovered panting she looked down and started laughing... " you missed your chance she smiled, and threw a pillow at me, "go make breakfast!" she barked playfully.
"Yes my lady" I replied sarcastically
"And don't you forget it." she said to my back as I headed to get dressed and follow instructions.
I had a broad grin on my face as she entered the kitchen to the smell of a full English. "Hmmm I could get used to this." she grinned.
"What's that?" I asked.
"Having a slave." she chortled.
"do you want to... Get used to it I mean?" I asked.
"Is that an offer?"
"I guess it is."
"You want to be my slave?"
"It's fun isn't it?"
"Hmmm, but you come so fast." she scolded.
"Sorry." I almost whispered and hung my head.
"No, I meant it can't be fun for you." she softened.
"Are you kidding me, I cum so fast because your so hot."
"OK I think I would like to try it for a while. Lets see if you can manage to fuck me!"
Wow, what had I just agreed to? It turns out it wasn't as kinky as I had expected. we fell in to a routine. things didn't improve with her mum, and without a word spoken it became official. I had a girlfriend. She had to go back to school at the end of summer just one more year, so I took responsibility for her. Our bedroom antics continued, we played all sorts of games and our bond grew stronger. We talked honest and open, never held back. she told me she didn't want me to take her virginity until I was sure there was a good chance I could make her come. But my premature ejaculation got worse. I didn't help that she would time me wanking and make fun of me, the more humiliated I felt the faster I came and she played on that and I loved it.
Around Christmas time I was surfing porn and I came across male chastity, it somehow seemed it might be a solution. At Christmas I presented her with a cage and she was at first very confused, then intrigued, then excited. It mad for some fun times. But by February it was clear it wasn't helping my problem. It did stop me jacking off or Cumming but as soon as it was off BOOM! game over. Plus It wasn't very comfortable or secure... It was easy to pick the lock or pull out. I decided to get my cock pierced In the hope it would de sensitise me a little and provide more secure chastity. At the same time I set about designing and making my own chastity tube.
It took a lot of measuring and engineering an research. I found a few sites online that offered custom built designs but they were hugely expensive. I persisted with it while my piercing healed and through this time Vicky was supportive and understanding. Our relationship was solid and honest and we both came to the unspoken realisation that without serious intervention my problem wasn't going away. I did research how I might work on my ejaculatory disfunction and there are many ways it can be overcome. But armed with all the knowledge of who to stop Cumming so fast I couldn't bring myself to do it. Every time I thought I might try, We would have a sex session, I would instantly cum and Vicky's scorn and humiliation of me and laughter, would set my heart on fire to pleasure her in what ever way I could. As for her she loved my devotion to her and my efforts to please her, and it was noticeable that she would encourage me to insta-cum, she seemed to enjoy that she was so hot I couldn't hold back.
Eventually my piercing had healed and my home made chastity tube was complete. It is like nothing else you have seen on the market. It consists of several different diameter tubes interlocked to hold and restrict my erections with a telescopic piece to ensure my whole erection is contained. It was time to present it to the love of my life. I arranged for a romantic dinner at a local restaurant and put the device in a presentation box.
It all started when I was quite young. I was rare for a 22 year old in that I was already quite wealthy as a property developer, so I didn't have to worry about working every day.
I was at my local Nightspot with a few mates on the lookout for any chance to find a girl. (A 22 year old virgin is pretty sad after all. I had had a few relationships but never manged the home run). It was getting towards the end of the night and I had just stepped out for some air. Looking into a dark corner I heard some soft sobbing. Curious and concerned I approached the source of the sound "Hey who's there" I called quietly, and suddenly I saw the most beautiful eyes shining back at me from the dark, clearly moist with tears. " Hey what's the matter?" I tried in my most non threatening, softest most comforting tone I could manage.
I fucking hate my life!" she replied now suddenly angry at the world.
"come on, I'll get you a drink and you can tell me about it." She perked up a little weather it was the offer of a drink or a sympathetic ear didn't really matter. As I walked her to the bar I finally had the chance to take in the rest of her. She was distinctly under dressed but through her jeans and t-shirt casual dress (odd for a Saturday night out) I could tell she had an amazing figure. I bought us a drink and took her to a dark quiet nook in the club. Very soon she started to open up. her parents had split up and her Dad was no where to be found. As a result her Mum was falling apart and was well on the way to being an alcoholic. It turns out she was only 16 (a month or two off 17,not jail bait but only just not). As a result she didn't want to go home and put up with all the crap that came with her situation.
I had just finished renovating my most recent property and it was fully furnished ready to be let, I had been staying there the last few days just finishing it off and thought hell why not. "Look," I said, " don't thing I am trying it on but you could stay at mine, at least until you get your bearings, no strings no sex nothing like that. What do you think?" I offered. She was stunned at first but then her face cracked into a massive smile and she nodded her agreement. After we finished our drinks I took her for a meal and then back to the house. I showed her to the master bedroom... a double and she turned to me with fear in her eyes and it struck me how that must have looked "Nonononoono.." I protested "I will be in here I!" said showing her the guest room. She visibly relaxed and I said my goodnights.
In the morning I made her some tea and toast, and took it to her in bed, politely knocking on the door I made a play on serving her in bed which she clearly found amusing so I played it up even more. " Today I want you to forget all about your troubles and treat me as your chauffeur and personal servant.
"Lets just go wander round town." she said. and so that's how I ended up on a shopping spree buying her lots of clothes. I even bought her some sexy lingerie. It somehow felt good, even though I still had no expectation of sex or the like. I just enjoyed making her happy. We spent the day shopping like mad and ended at a restaurant where of course I picked up the tab. She had a few glasses of wine or three and being young got tipsy quite fast. Being the knight in shining armour as I saw myself at this point, I took her home and we sat and watched a movie. She snuggled up to me and in her hazy state I am sure she didn't realise that I felt the full advantage of her ample young pert breasts rubbing against me.
I was instantly horny of course, but also very conscious that I could not take advantage of this innocent young girl. as the film came to an end and I saw the possibility to get away from the situation and relieve my tension the way any horny bloke would. She clambered on top of me and whispered, let me thank you. I was ready to stop her when I realised all she meant was a kiss, so I relaxed a little. That was when I felt the top of her thigh pressing into my groin, and as the smooch continued my body betrayed me and I stated humping her leg. It must have been less than a minute of this bliss when my orgasm took me. Sudden, hard and fast. There was no way I could hide it as i grabbed her firmly and thrust against her. as the waves of pleasure receded I heard the most wonderful sound. Like an angel laughing in sheer joy but also mockery.
"So your not such a saint after all." she chuckled, "Dirty little fucker just came in your pants,, didn't you?" I couldn't help it her mocking words and light tone made my heart flutter.
"Y... Yess." I managed to gas, adding, "Your too much for me." I let out a sigh, as I let my ego go along with it. Snickering she drove her thigh into my groin again as she snuggled down on my chest.
" I've never made a man come before." she admitted.
"I bet loads of boys have wanked thinking about you." I offered.
"You think so?"
"I know so. You really are hot, and should learn to use it."
"Will you teach me?" she asked, " And who knows in time maybe you can fuck me." She bit her lip and I could see her words shocked her and embarrassed her but also oddly turned her on to be so brazen.
"Well, you have made a great start."
Ewww its all slimy!" she suddenly shrieked and clambered up. A glob of my spunk has seeped through my pants and was clinging to her bare thigh where her nightshirt had ridden up. She saw me looking and bit her lip again. "You dirty pervert, you like that don't you?"
"ughhn!" was all I could manage
"You getting horny again? she asked.
"That obvious huh?"
"Strip then but stay on the floor. I don't want you getting any ideas."
I didn't need asking twice and my clothes were off in record time. I sat on the floor my legs spread so my cock was laid on the floor and I still couldn't take my eyes of my spunk just clinging to her leg, like it was still a part of my body.
"So what do you want to do?" she asked inching closer and raising the nightshirt and tantalisingly close to revealing her panties.
"May I kiss you leg please?" even to me I sounded pathetic but I didn't care I was desperate.
"OK but just to be sure you don't get any ideas..." She stepped forward offering the leg with cum on but stood on my cock, pinning it to the floor and hooked her other leg over my shoulder. My face was level with the cum and I looked up. I could just see her eyes sparkling down at me, staring with intent interest. I started placing light kisses on her leg around my slime and my cock went into overdrive, I wriggled getting as much movement into my cock as I could and the more I wriggled the more weight she put on me. Soon she had all her weight on me but it wasn't enough and I really had my wank on. I couldn't resist any longer an I was overcome with lust, as I felt my orgasm build I opened my moth and slurped my cum off her leg. "OOOOH! she exclaimed and my cock stated to spasm. I knew she could feel it under her foot and she was giggling like the schoolgirl she was.
Fuck my head was spinning there I was with a schoolgirl standing on my cock as I licked my spunk off her and she was laughing at ... and I loved it. Instead of jumping away she seemed to instinctively know to keep the pressure on, and rather she ground her foot on my cock making the last spurts even more intense. I clung on to her leg and she was reassured that she had the right to grind on me as much as she liked.
"All done wanker?" she chided me. I responded by kissing her leg as far up as I could reach.. about an inch short of her crotch. She stroked my head seemingly to comfort me. "Wow... I guess your right, I am sexy." she said. Not an ounce of sarcasm or irony.
"Ehhm," I cleared my throat, "First lesson." I managed to croak.
"Who for? Me or you?" I hugged her leg and grinned up at her...
"Both! Lets get something to eat." I suggested.
"You could lick up the mess you made." she started laughing hysterically and flounced into the kitchen. I grabbed my T-shirt and cleaned up and followed her.
When we got upstairs at her bedroom door she turned to me, "...... with me, please." I was shocked and so mutely followed. She stripped naked and proved me right, she was perfect, even her bush was trimmed. she climbed int bed and I followed. Having come twice I was not about to get a spontaneous hard-on and I still didn't want to breach the trust we were developing. But I found it easy to just cuddle and comfort her untill we both fell asleep.
The next morning I woke up with her nuzzling at my chest and felt her delicate hand explore my groin. Needless to say instant morning wood. She grinned up at me and said "I've decided.. I... I want you to fuck me." before I could answer she kissed me, "Fuck me, please fuck me" kiss. I returned the kiss and flipped her over laying on top of her and making out. I wriggled around trying for position to get us both comfortable and she opened her legs giving me full access to penetrate. I thrust towards her and my cock head made contact with her pussy and I could tell it was moist. I gave another few short thrusts hoping to find her opening but just like the previous night suddenly and without much warning I exploded.
"urghhhhhh!" she let out in clear frustration
"Oh god I am so sorry, but you caught me unprepared. Oh god. Let me make it up to you"
How?" she snapped
"Anything." I pleaded.
"Go down on me then!" she demanded.
"Uh err but I just came."
"So, its your mess and you licked it up last night... go down and clean me!" She actually sounded angry, but there was still a hint of playfulness in it, and I sensed she was seeing how far she could push me. I suddenly realised I wanted her to push me as far as she wanted, and I would go. I threw off the covers and slid down the bed. I wasn't going to balk at this point and started licking my cum up, It was a little watery having cum twice the night before but there was still lots of it.. I licked it up quickly and set to work licking the cutest wettest most amazing virgin pussy ever created, and she started writhing around obviously enjoying the tonging I was giving her. Seeing her turned on pushed my buttons and I was soon hard again. "all may not be lost," I thought I might still pull this off." As I licked I manoeuvred my cock onto her foot and started humping, hoping she would notice and invite me to try again. But she was lost in her own pleasure grinding on my face. And so we continued for about 20 minutes, until I sensed she was close. she pulled on the back of my head and tensed up, jabbing her foot hard into my balls she was Cumming ... and so was I.
As she recovered panting she looked down and started laughing... " you missed your chance she smiled, and threw a pillow at me, "go make breakfast!" she barked playfully.
"Yes my lady" I replied sarcastically
"And don't you forget it." she said to my back as I headed to get dressed and follow instructions.
I had a broad grin on my face as she entered the kitchen to the smell of a full English. "Hmmm I could get used to this." she grinned.
"What's that?" I asked.
"Having a slave." she chortled.
"do you want to... Get used to it I mean?" I asked.
"Is that an offer?"
"I guess it is."
"You want to be my slave?"
"It's fun isn't it?"
"Hmmm, but you come so fast." she scolded.
"Sorry." I almost whispered and hung my head.
"No, I meant it can't be fun for you." she softened.
"Are you kidding me, I cum so fast because your so hot."
"OK I think I would like to try it for a while. Lets see if you can manage to fuck me!"
Wow, what had I just agreed to? It turns out it wasn't as kinky as I had expected. we fell in to a routine. things didn't improve with her mum, and without a word spoken it became official. I had a girlfriend. She had to go back to school at the end of summer just one more year, so I took responsibility for her. Our bedroom antics continued, we played all sorts of games and our bond grew stronger. We talked honest and open, never held back. she told me she didn't want me to take her virginity until I was sure there was a good chance I could make her come. But my premature ejaculation got worse. I didn't help that she would time me wanking and make fun of me, the more humiliated I felt the faster I came and she played on that and I loved it.
Around Christmas time I was surfing porn and I came across male chastity, it somehow seemed it might be a solution. At Christmas I presented her with a cage and she was at first very confused, then intrigued, then excited. It mad for some fun times. But by February it was clear it wasn't helping my problem. It did stop me jacking off or Cumming but as soon as it was off BOOM! game over. Plus It wasn't very comfortable or secure... It was easy to pick the lock or pull out. I decided to get my cock pierced In the hope it would de sensitise me a little and provide more secure chastity. At the same time I set about designing and making my own chastity tube.
It took a lot of measuring and engineering an research. I found a few sites online that offered custom built designs but they were hugely expensive. I persisted with it while my piercing healed and through this time Vicky was supportive and understanding. Our relationship was solid and honest and we both came to the unspoken realisation that without serious intervention my problem wasn't going away. I did research how I might work on my ejaculatory disfunction and there are many ways it can be overcome. But armed with all the knowledge of who to stop Cumming so fast I couldn't bring myself to do it. Every time I thought I might try, We would have a sex session, I would instantly cum and Vicky's scorn and humiliation of me and laughter, would set my heart on fire to pleasure her in what ever way I could. As for her she loved my devotion to her and my efforts to please her, and it was noticeable that she would encourage me to insta-cum, she seemed to enjoy that she was so hot I couldn't hold back.
Eventually my piercing had healed and my home made chastity tube was complete. It is like nothing else you have seen on the market. It consists of several different diameter tubes interlocked to hold and restrict my erections with a telescopic piece to ensure my whole erection is contained. It was time to present it to the love of my life. I arranged for a romantic dinner at a local restaurant and put the device in a presentation box.