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StrappedMatt

Jockstrap Fan
The first time I ever wore a cup was at my friend Josh's house. I played baseball with him from t-ball all the way through little league, then into high school. One day as kids we were at his house and going to throw the ball around, but I had left my glove at home. He pointed for me to use his dad's glove, and when I picked it up, his dad's jock and cup fell out of it. We laughed at how big the cup was. He then shoved it down his pants, tossed me the ball, and said "I bet you can't hit me in the nads!". He could turn and duck and bend with no glove, and wasn't allowed to move his feet. I threw it at him but hit him in the side as he turned. He yelled out in pain and we laughed. I tried a few more time and finally hit him in the groin. He pulled the cup out and handed it to me - "Your turn!". I first put it between my shorts and my tighty whities, but it immediately fell out through my shorts and hit the ground. Josh said, "In your underwear!" So I put his dad's cup in my briefs and stood there, staring down at it. Josh then, from 15 feet away, threw a direct hit, knocking me back and onto the ground. I looked at him in shock, pain, and then laughter.

We did that for a bit until his dad came walking out of the garage and saw what we were up to. I had the cup on again at that point, and his dad looked down at the cup and rolled his eyes. He said, "Y'all are idiots. ..... Here, give it. My turn" and motioned for the cup. I took it out and awkwardly handed it over. He was maybe 6'1, muscular, and wearing jeans a t-shirt. He undid his jeans and put the cup down the front his briefs. He couldn't zip up with it in there, so he left the front of his jeans open wide, his white briefs bulging out. He told us "if you can knock this cup, I'll order pizza. If you can't, I'll order pizza and you'll run laps until it gets here." He caught a few balls bare-handed, knocked some down, but eventually Josh really threw one and hit his dad right in the nuts. He winced, pulled out the cup, tossed it back to me, and barked "Put this back where you found it! ...... What pizza do you idiots want?" I remember how warm his cup felt as I carried it back inside their house.

That year coach started requiring players to wear a jock and all batters and infielders to wear a cup, so I would get one of my own. Josh's dad ended up getting it for me, but that's a different story.
 

Redsucked02

More in my albums!
The first time I ever wore a cup was at my friend Josh's house. I played baseball with him from t-ball all the way through little league, then into high school. One day as kids we were at his house and going to throw the ball around, but I had left my glove at home. He pointed for me to use his dad's glove, and when I picked it up, his dad's jock and cup fell out of it. We laughed at how big the cup was. He then shoved it down his pants, tossed me the ball, and said "I bet you can't hit me in the nads!". He could turn and duck and bend with no glove, and wasn't allowed to move his feet. I threw it at him but hit him in the side as he turned. He yelled out in pain and we laughed. I tried a few more time and finally hit him in the groin. He pulled the cup out and handed it to me - "Your turn!". I first put it between my shorts and my tighty whities, but it immediately fell out through my shorts and hit the ground. Josh said, "In your underwear!" So I put his dad's cup in my briefs and stood there, staring down at it. Josh then, from 15 feet away, threw a direct hit, knocking me back and onto the ground. I looked at him in shock, pain, and then laughter.

We did that for a bit until his dad came walking out of the garage and saw what we were up to. I had the cup on again at that point, and his dad looked down at the cup and rolled his eyes. He said, "Y'all are idiots. ..... Here, give it. My turn" and motioned for the cup. I took it out and awkwardly handed it over. He was maybe 6'1, muscular, and wearing jeans a t-shirt. He undid his jeans and put the cup down the front his briefs. He couldn't zip up with it in there, so he left the front of his jeans open wide, his white briefs bulging out. He told us "if you can knock this cup, I'll order pizza. If you can't, I'll order pizza and you'll run laps until it gets here." He caught a few balls bare-handed, knocked some down, but eventually Josh really threw one and hit his dad right in the nuts. He winced, pulled out the cup, tossed it back to me, and barked "Put this back where you found it! ...... What pizza do you idiots want?" I remember how warm his cup felt as I carried it back inside their house.

That year coach started requiring players to wear a jock and all batters and infielders to wear a cup, so I would get one of my own. Josh's dad ended up getting it for me, but that's a different story.
Do tell please!
 

BillyC

If not commando, then jocked.
The first time I ever wore a cup was at my friend Josh's house. I played baseball with him from t-ball all the way through little league, then into high school. One day as kids we were at his house and going to throw the ball around, but I had left my glove at home. He pointed for me to use his dad's glove, and when I picked it up, his dad's jock and cup fell out of it. We laughed at how big the cup was. He then shoved it down his pants, tossed me the ball, and said "I bet you can't hit me in the nads!". He could turn and duck and bend with no glove, and wasn't allowed to move his feet. I threw it at him but hit him in the side as he turned. He yelled out in pain and we laughed. I tried a few more time and finally hit him in the groin. He pulled the cup out and handed it to me - "Your turn!". I first put it between my shorts and my tighty whities, but it immediately fell out through my shorts and hit the ground. Josh said, "In your underwear!" So I put his dad's cup in my briefs and stood there, staring down at it. Josh then, from 15 feet away, threw a direct hit, knocking me back and onto the ground. I looked at him in shock, pain, and then laughter.

We did that for a bit until his dad came walking out of the garage and saw what we were up to. I had the cup on again at that point, and his dad looked down at the cup and rolled his eyes. He said, "Y'all are idiots. ..... Here, give it. My turn" and motioned for the cup. I took it out and awkwardly handed it over. He was maybe 6'1, muscular, and wearing jeans a t-shirt. He undid his jeans and put the cup down the front his briefs. He couldn't zip up with it in there, so he left the front of his jeans open wide, his white briefs bulging out. He told us "if you can knock this cup, I'll order pizza. If you can't, I'll order pizza and you'll run laps until it gets here." He caught a few balls bare-handed, knocked some down, but eventually Josh really threw one and hit his dad right in the nuts. He winced, pulled out the cup, tossed it back to me, and barked "Put this back where you found it! ...... What pizza do you idiots want?" I remember how warm his cup felt as I carried it back inside their house.

That year coach started requiring players to wear a jock and all batters and infielders to wear a cup, so I would get one of my own. Josh's dad ended up getting it for me, but that's a different story.
See THIS is the kind of childhood/growing up I had. No porn script playing out, not even when my oldest brother caught me jacking off with his sweaty jockstrap. Just boys being stupid about masculinity and stuff we had to learn along the way.
 

packedstrap

Jockstrap Fan
The first time I ever wore a cup was at my friend Josh's house. I played baseball with him from t-ball all the way through little league, then into high school. One day as kids we were at his house and going to throw the ball around, but I had left my glove at home. He pointed for me to use his dad's glove, and when I picked it up, his dad's jock and cup fell out of it. We laughed at how big the cup was. He then shoved it down his pants, tossed me the ball, and said "I bet you can't hit me in the nads!". He could turn and duck and bend with no glove, and wasn't allowed to move his feet. I threw it at him but hit him in the side as he turned. He yelled out in pain and we laughed. I tried a few more time and finally hit him in the groin. He pulled the cup out and handed it to me - "Your turn!". I first put it between my shorts and my tighty whities, but it immediately fell out through my shorts and hit the ground. Josh said, "In your underwear!" So I put his dad's cup in my briefs and stood there, staring down at it. Josh then, from 15 feet away, threw a direct hit, knocking me back and onto the ground. I looked at him in shock, pain, and then laughter.

We did that for a bit until his dad came walking out of the garage and saw what we were up to. I had the cup on again at that point, and his dad looked down at the cup and rolled his eyes. He said, "Y'all are idiots. ..... Here, give it. My turn" and motioned for the cup. I took it out and awkwardly handed it over. He was maybe 6'1, muscular, and wearing jeans a t-shirt. He undid his jeans and put the cup down the front his briefs. He couldn't zip up with it in there, so he left the front of his jeans open wide, his white briefs bulging out. He told us "if you can knock this cup, I'll order pizza. If you can't, I'll order pizza and you'll run laps until it gets here." He caught a few balls bare-handed, knocked some down, but eventually Josh really threw one and hit his dad right in the nuts. He winced, pulled out the cup, tossed it back to me, and barked "Put this back where you found it! ...... What pizza do you idiots want?" I remember how warm his cup felt as I carried it back inside their house.

That year coach started requiring players to wear a jock and all batters and infielders to wear a cup, so I would get one of my own. Josh's dad ended up getting it for me, but that's a different story.
I love it that he said "my turn" then joined in
 
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