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Anything Goes
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Straight Male / 60
Wife Decided I Needed A Apprentice
My wife felt I should get a new apprentice. Someone to grab tools cleanup and at the end of the day roll up tools. I am 60 still in good shape but it is nice to have someone doing the grunt work.
One of our 20 something kids told her a friend was looking to learn how to build. They tell me he is 18 just about 19 so I have them arrange for him to come over. Meet me at my shop to talk interview as such. Lets call him J
I am working away when J gets to my shop and comes in and what I see is this tiny 5' maybe 100lb very feminine boy. So we chat and it becomes clear this is J has no experience has never work with their hands but feel called too so I tell them I will give them a opportunity to experience construction and see what they think. After I go in the house my wife is grinning ear to ear and asked me how it went I knew it was a setup she explained that they had just changed pronouns after graduating and had struggled to find a job in construction. and she knew I would give them a chance.
So first day comes J is on time. We get in the truck travel to a project . We have our first conversations I find J competed in gymnastics and dance since they were 5 and had basically a normal very upper middle class childhood. First couple months is mostly just learning what all the tools are and where they go in my truck and how to safely use everything. I am a big man 6' 9" close to 265lbs at 60 years old a 100 burpies sucks but I can do them. so decently fit. One thing J impressed me with was just how strong they were for their size.
So in construction you get to know everything happening in your employs lives if you talk to them or listen.
J was struggling because they had always felt asexual with no arousal at anything. had tried sex with boys and girls and just nothing. and felt being a Man would let them live more peacefully than as a Woman.
Then they started taking Testosterone and it kicked loose a storm of emotions a few months into that they had a melt down one day and I opened my arms then j literally crawled across my truck cab and curled up in my lap. While I am holding them they confessed that their dreams were sexual and all they could think about was sex and everything made them horny. I belly laughed so hard and said welcome to being a teenage boy. I just held them and of course his little perfect sculpted rock hard butt was perched on my cock and it started to press up while I held them and J lift his face and softly asked if they were causing that. I told them Yes you are. J kissed me then. As I started running my hands over their body it was like I had electrified my hands J's body just rippled. I have no idea how we got their pants off or mine down because I can barely move around in most vehicle cabs. but in short order they sank down on my cock I am not massively endowed all big man jokes aside at 7" in length I have a 6" shaft with I am told a very large cockhead that gets even larger when I come close to cumming. So J with little sex experience was gasping and breathing deep like she had just enter freezing cold water and his pussy was so tight and snug and with every breathe it would contract. I pulled their chest to mine and held them for a moment. I kissed the top of their head and they looked up at me beaming and asked if they could ride my cock please. I told them they better or I was going spank their little butt. J then started working up and down taking longer and longer strokes until just my cockhead was inside them then Plunging to the hilt I was cradling their butt in my hands its felt so good and after a bit they orgasmed so hard they blacked out for a moment and I pulled the close again. J came to and asked what was that. I told them you had a Orgasm J had never had one even trying to masterbate had never had one. Feeling a bit to sensitive and stilll trembling J dismounted me and then after getting back in their seat looked at my still hard cock and asked what they could I asked if they had ever given a blowjob and they had so i asked if they would suck me and they agreed to. well my cockhead was in state that it was hard for them to get it in their sweet little mouth with their tiny hand wrapped around my shaft and sucking my cockhead I blew a huge load in J mouth and they consumed it all. I told them what good boy they were and J crawled back in my lap and told me she would be a Good Girl for me anytime I wanted.
One of our 20 something kids told her a friend was looking to learn how to build. They tell me he is 18 just about 19 so I have them arrange for him to come over. Meet me at my shop to talk interview as such. Lets call him J
I am working away when J gets to my shop and comes in and what I see is this tiny 5' maybe 100lb very feminine boy. So we chat and it becomes clear this is J has no experience has never work with their hands but feel called too so I tell them I will give them a opportunity to experience construction and see what they think. After I go in the house my wife is grinning ear to ear and asked me how it went I knew it was a setup she explained that they had just changed pronouns after graduating and had struggled to find a job in construction. and she knew I would give them a chance.
So first day comes J is on time. We get in the truck travel to a project . We have our first conversations I find J competed in gymnastics and dance since they were 5 and had basically a normal very upper middle class childhood. First couple months is mostly just learning what all the tools are and where they go in my truck and how to safely use everything. I am a big man 6' 9" close to 265lbs at 60 years old a 100 burpies sucks but I can do them. so decently fit. One thing J impressed me with was just how strong they were for their size.
So in construction you get to know everything happening in your employs lives if you talk to them or listen.
J was struggling because they had always felt asexual with no arousal at anything. had tried sex with boys and girls and just nothing. and felt being a Man would let them live more peacefully than as a Woman.
Then they started taking Testosterone and it kicked loose a storm of emotions a few months into that they had a melt down one day and I opened my arms then j literally crawled across my truck cab and curled up in my lap. While I am holding them they confessed that their dreams were sexual and all they could think about was sex and everything made them horny. I belly laughed so hard and said welcome to being a teenage boy. I just held them and of course his little perfect sculpted rock hard butt was perched on my cock and it started to press up while I held them and J lift his face and softly asked if they were causing that. I told them Yes you are. J kissed me then. As I started running my hands over their body it was like I had electrified my hands J's body just rippled. I have no idea how we got their pants off or mine down because I can barely move around in most vehicle cabs. but in short order they sank down on my cock I am not massively endowed all big man jokes aside at 7" in length I have a 6" shaft with I am told a very large cockhead that gets even larger when I come close to cumming. So J with little sex experience was gasping and breathing deep like she had just enter freezing cold water and his pussy was so tight and snug and with every breathe it would contract. I pulled their chest to mine and held them for a moment. I kissed the top of their head and they looked up at me beaming and asked if they could ride my cock please. I told them they better or I was going spank their little butt. J then started working up and down taking longer and longer strokes until just my cockhead was inside them then Plunging to the hilt I was cradling their butt in my hands its felt so good and after a bit they orgasmed so hard they blacked out for a moment and I pulled the close again. J came to and asked what was that. I told them you had a Orgasm J had never had one even trying to masterbate had never had one. Feeling a bit to sensitive and stilll trembling J dismounted me and then after getting back in their seat looked at my still hard cock and asked what they could I asked if they had ever given a blowjob and they had so i asked if they would suck me and they agreed to. well my cockhead was in state that it was hard for them to get it in their sweet little mouth with their tiny hand wrapped around my shaft and sucking my cockhead I blew a huge load in J mouth and they consumed it all. I told them what good boy they were and J crawled back in my lap and told me she would be a Good Girl for me anytime I wanted.
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