Straight Male / 60
J The Apprentice Is Still Working For Me
Well J has not quit yet.
Recap my wife thought I could use a apprentice. 60 year old general contractor 6' 9" 268lbs
J Male pronoun cis female 19 years old now 5' and I thought weighed under 100lbs turns out solid gymnast weighs 108lbs.
Taking testosterone took them from asexual to sex crazed with us having sex in my truck and dozens of times after that. Since then they consulted with their Doctor they have stopped taking testosterone and are proceeding slower.
J oddly having bonded to me and desiring to be a girl for just me. My wife and I do have a unique relationship and she knows everything thing that has happened. Knowing I do enjoy being a dirty Daddy and witnessing me always finding the girls who desire my attention.
J is doing great at learning construction.
I took J with me to a seminar in Vegas and upon arrival took them shopping and bought them the skimpiest clothes they had ever seen from none existent G string barely a belt as a skirt and tiny top that was shear enough to see through. With a full makeover pedicure manicure with hair and makeup. She greeted me with a squeal of delight and a loud Daddy look and a twirl and pose. Followed by leaping up and me catching her to receive a very not Daddy Daughter kiss.
Got a few disgusted looks from other women and couple girls that worked there and big smile from the girl who walked her out.
Well J has taken to pleasing Daddy as she calls me. If I enjoy it she wants me to have it and her amazing tight pussy and talented tiny mouth are incredibly pleasurable her tight little virgin ass has been Daddies obsession. It has taken us a couple months of work to get them comfortable just having my cockhead partially inserted and I know just push harder it will go in crowd thinks it is unnecessary to take my time. I know I can cause tears that will make it painful for her every time she gets anally penetrated if I force her to soon. So Daddy has been patient and had to hold J back as she is been ready to force herself down on it to please Daddy since we started. Today Daddies Cockhead slipped in past both of her sphincter muscles as she rode me and I got to feel her gasp as she slid down my shaft a bit. Since she is so small I pulled her to me and rolled forward to lay her on her back and so I could slowly push in and control how deep I went. I pulled out a bit she asked me if Daddy want her on her Belly. She knows this is how Daddy want her. very carefully I pulled out and added more lube J got on her belly and lifted her perfect little butt up and Daddy slowly pushed his Cockhead into the tightest little ass he has ever fucked. They slowly over time finally took all Daddy had to give I laid over them praising them for being such a good girl for Daddy and telling them just how amazing it felt. J was telling me to fuck Daddies Special Hole and to Cum deep inside. I finally felt a huge orgasm building and told them as the first blast of cum shot inside them. J exclaimed she could feel me cumming and to please don't stop. Well finally I collapsed spent and laid there pinning J under me. As I finally softened I rolled off J and pulled them up on my chest. She was beaming and declared she did it she took my whole cock up her ass. I kissed her and told her it was all mine now. She told me anytime Daddy anytime. I hope she means it :) she could barely walk when we boarded the plane 2 days latter. Though Daddy being honest could hardly walk either.
So I have a apprentice in work and life again.
My wife enjoying much more romantic gentle sex is happy I have a outlet for my Dominant Daddy side.
J has been living with us now since Vegas and we are going to close out their lease when it ends. Much easier for Daddy to use his girl before or after work when they live under the same roof.
Will update as this goes on. The smiling girl from the salon in Vegas had given J her number J was shocked but I told J she should get used to other girls hitting on her.
Recap my wife thought I could use a apprentice. 60 year old general contractor 6' 9" 268lbs
J Male pronoun cis female 19 years old now 5' and I thought weighed under 100lbs turns out solid gymnast weighs 108lbs.
Taking testosterone took them from asexual to sex crazed with us having sex in my truck and dozens of times after that. Since then they consulted with their Doctor they have stopped taking testosterone and are proceeding slower.
J oddly having bonded to me and desiring to be a girl for just me. My wife and I do have a unique relationship and she knows everything thing that has happened. Knowing I do enjoy being a dirty Daddy and witnessing me always finding the girls who desire my attention.
J is doing great at learning construction.
I took J with me to a seminar in Vegas and upon arrival took them shopping and bought them the skimpiest clothes they had ever seen from none existent G string barely a belt as a skirt and tiny top that was shear enough to see through. With a full makeover pedicure manicure with hair and makeup. She greeted me with a squeal of delight and a loud Daddy look and a twirl and pose. Followed by leaping up and me catching her to receive a very not Daddy Daughter kiss.
Got a few disgusted looks from other women and couple girls that worked there and big smile from the girl who walked her out.
Well J has taken to pleasing Daddy as she calls me. If I enjoy it she wants me to have it and her amazing tight pussy and talented tiny mouth are incredibly pleasurable her tight little virgin ass has been Daddies obsession. It has taken us a couple months of work to get them comfortable just having my cockhead partially inserted and I know just push harder it will go in crowd thinks it is unnecessary to take my time. I know I can cause tears that will make it painful for her every time she gets anally penetrated if I force her to soon. So Daddy has been patient and had to hold J back as she is been ready to force herself down on it to please Daddy since we started. Today Daddies Cockhead slipped in past both of her sphincter muscles as she rode me and I got to feel her gasp as she slid down my shaft a bit. Since she is so small I pulled her to me and rolled forward to lay her on her back and so I could slowly push in and control how deep I went. I pulled out a bit she asked me if Daddy want her on her Belly. She knows this is how Daddy want her. very carefully I pulled out and added more lube J got on her belly and lifted her perfect little butt up and Daddy slowly pushed his Cockhead into the tightest little ass he has ever fucked. They slowly over time finally took all Daddy had to give I laid over them praising them for being such a good girl for Daddy and telling them just how amazing it felt. J was telling me to fuck Daddies Special Hole and to Cum deep inside. I finally felt a huge orgasm building and told them as the first blast of cum shot inside them. J exclaimed she could feel me cumming and to please don't stop. Well finally I collapsed spent and laid there pinning J under me. As I finally softened I rolled off J and pulled them up on my chest. She was beaming and declared she did it she took my whole cock up her ass. I kissed her and told her it was all mine now. She told me anytime Daddy anytime. I hope she means it :) she could barely walk when we boarded the plane 2 days latter. Though Daddy being honest could hardly walk either.
So I have a apprentice in work and life again.
My wife enjoying much more romantic gentle sex is happy I have a outlet for my Dominant Daddy side.
J has been living with us now since Vegas and we are going to close out their lease when it ends. Much easier for Daddy to use his girl before or after work when they live under the same roof.
Will update as this goes on. The smiling girl from the salon in Vegas had given J her number J was shocked but I told J she should get used to other girls hitting on her.
