Caught Dressed By My Much Younger Roommate!
I had a 4-bedroom house, just me (51). This local bar where I hang out had just hired a college kid (22 years old) for a summer job.
After a couple of weeks, one of the servers mentioned that he was looking for a room to rent. Knowing I had an extra room, she asked if I would be interested in renting a room to him until fall. Having already gotten to know him a little, we agreed he could move in as soon as he was ready.
I did not do it just to help him out. The girl he was seeing was just smoking hot. The thought of seeing her and some of her girlfriends hanging around all the time, especially using the pool would be a bonus.
I only had one concern.
I had just started crossdressing for about a year before he moved in, mostly every weekend. By that time, I was dressing all out. Hair, make-up, boobs, nails, sexy outfits, etc. None of my family and friends knew about Robin, and (except for a couple times camming online) no one had ever seen me dressed up. So, I figured I would have to cut way back on my playtime. Having such a large house with my master bedroom at the far end of the house, I thought I could still safely dress every now and then until he went back to school in three months.
Or so I thought....
About three to four weeks after he moved in, I was all dressed up on a Friday night chatting and camming online. Around 2am, I heard him drive up and come inside. If he came home alone, he would just go to his end of the house. Usually, we would not see each other until morning. This time I heard him mess around in the kitchen for a few minutes, then total silence.
Soon I could hear him again, figuring he was going to his end of the house.
Suddenly, he knocks on my bedroom door. Now I go into full panic mode because I am completely dressed! Hair, make-up, nails, etc. I was wearing a tight black bodycon mini dress, my size D boobs with matching bra and lace thong panties. I finished off the look with thigh-high lace top stockings and black six-inch heels.
There is no way I can get undressed quickly. I am thinking if I do not answer he will go away. I am not that lucky! He knocks again, a little louder.
With my hands and knees shaking, I walk up and ask him through the door what he wants.
He replies, "Let me in, I know what you are doing".
As you can imagine I was speechless. All these thoughts of being busted raced through my head. It seemed like time stood still as I struggled to come up with some kind of response. Resigning to my fate of finally being busted, I said "Wait 30 seconds and then come in". I then turned off the overhead light, unlocked the door and jumped into bed. In my high heels and dress and covered up head to toe.
He opened the door and walked in. Taking a few seconds for his eyes to adjust, he looks at me and smiles. Seeing me all covered up he says, "You don't have to cover up, as a matter of fact get up and let me take a good look at you".
I am thinking, "Oh my god". But I moved the covers off and stood up. After I pulled my dress back down, I slowly walked over and stood just a few feet from him.
He said, "Wow you look great!". "Turn around for me". I do as he asks. Surprised that I have not tripped and fallen! Lol. I am in serious sensory overload. I have no idea what is going to happen.
I can feel that he has moved up right behind me. When his hands touch my hips, it is like an electric shock over my whole body. His face nuzzles into my hair and neck.
"Oh, you smell so good".
One of his hands glides up to my boobs, while the other slides down and stops just at the bottom of my dress. He plays with my stocking top for a second then slides up and encounters my bare cheek.
"You are so soft and smooth, I've got to see this". Gently he pushes me forward until I am at the end of the bed.
"Bend over the bed and spread your legs a little more."
He pulls my dress up to my waist and really starts feeling my cheeks. As I am trying not to moan like a slut, he says "This is going to be so much fun tonight!".
Standing me up and turning me back around forcefully. He pulls me in tight and gives me a very passionate kiss. After we break apart from that, he steps back and starts taking off his clothes. As I am watching him do that, I finally say something, asking him how he knew.
He said, “Well two ways, the first thing I noticed was lipstick-stained cigarettes in the ashtray on the back deck and last weekend I parked down the street and peeked in your bedroom window.”
I said, “You watched me through the window?”
He said, “Oh yes, for about an hour and I almost snuck in when you left your bedroom door open! I wanted to come in and just fuck the hell out of you. I was not sure how you would react, so I chickened out. Tonight, I peeked in again and saw you dressed all sexy again. Also, I noticed you were watching CD's getting fucked porn, so I knew you would be okay”.
About the time he finished talking, I noticed he only had his boxers on. There was a huge bulge in them. He caught me staring and laughed saying "You're going to take those off for me".
It just seemed natural to get on my knees as I took a few deep breaths. I was just inches away from seeing and touching my first cock.
My first hard cock.
A cock that I made hard.
Slowly I pulled his boxers down and yes. His cock sprang up and hit my chin!
It was about seven to eight inches long. He was also uncircumcised. The tip was very small to start but his whole cock grew very wide after the head.
Reaching out, I gently wrapped my hand around his cock. It felt so hard and yet soft at the same time. After a few seconds of staring at it, I started kissing and licking the head. Hearing him moan made me put more and more in my mouth. I had worked up to having six inches of cock in my mouth, when he put his hands on my head and started moving his cock in and out. Besides choking and gagging a few times, I held up well.
His thrusts and moans got faster, and I knew he was close to cumming. Just as I thought he was going to cum in mouth, he stopped. Pulling his cock out of my mouth, he looked down at me.
He said, "I do not want to cum yet, I've got other plans".
Looking right into my eyes he asked, "Besides those toys I saw you playing with last week, you're a virgin, aren't you?"
I said, "Yes I am."
He started laughing a little and said, "I'm going to enjoy fucking the hell out of you!"
He helped me up and guided me towards the bed. My four-poster bed is about waist high. Perfect height for him to bend me over.
Getting behind me, he lifted my dress over my butt.
At this point, I had so many thoughts and feelings going through my head I could barely speak. My hands and legs were shaking. When he started to rub his cock up and down between my cheeks, I squeaked out, "There is some lube on the nightstand".
When he got back, my thong panties were just pulled to the side. I looked back and saw him pouring the lube on his cock, then all over my butt. The feeling of him gently trying to get his cock in me was almost indescribable. He would just barely get the tip in, and then pull it out. This went on for a good five minutes. Soon, I noticed that I was pushing back, trying to get it in.
He said, "Okay, I think your tight little pussy is ready". I felt the tip go in again, but this time he kept a slow and steady push in me. The next thing I remember is when I felt his hips against my butt.
He said, "Oh my God you are so tight".
I think I babbled incoherently as he began slowly fucking me with long deep strokes.
I held on for dear life as he started going faster and faster. My clearest memory was hearing our bodies slapping together. Also, I remember him saying things to me. Like, "Do you like that cock?" and "You're a good slut". But all that paled in comparison when he yelled out, "I'm cumming" as he went as deep as he could and just held it there. I could feel his cock pulse over and over unloading his cum in me. He collapsed on my back, and we lay there for at least ten minutes.
Standing up behind me he gave me a light spank on the butt and started to pull it out. It was then that I realized how deep it was in me and how much cum there was. Cum started running down both of my legs.
I laughingly said, "I have to go clean up!".
That is when he replied, "Oh no! I am going to use that as lube in a few minutes".
He did me two more times that night, in every position he could think of.
We got together every weekend until he went back to school.
Looking back, I am glad it happened this way. It did wonders for my confidence. It would have taken me two years plus to get up the nerve to have my first date.
A good-looking college kid? 25+ years younger and he kept coming back for more? Wow! I started going out dressed in public (nighttime, lol!) on dates.
About our third time together, he told me about two of his friends (his age). They had talked about me and wanted to join us. However, they lived in town, and I knew them from the bar. It would have been too risky.
I ran into him and his girlfriend the following summer at that same bar (I was not dressed). We all talked like normal until she went to the bathroom. Very quietly he asked me if I was still dressing.
I’m sure I turned beet red as I just nodded my head.
He said, “I sure would love to see you again sometime. You are a great piece of ass! “
I almost spit up my beer when he said that! Lol!
I told him I still had the same number and he knew my schedule.
We saw his girlfriend coming back to rejoin us, and soon after they left.
Overall, I’m glad he caught me. It turned out perfectly!
PS: He texted me the following Friday night…….
After a couple of weeks, one of the servers mentioned that he was looking for a room to rent. Knowing I had an extra room, she asked if I would be interested in renting a room to him until fall. Having already gotten to know him a little, we agreed he could move in as soon as he was ready.
I did not do it just to help him out. The girl he was seeing was just smoking hot. The thought of seeing her and some of her girlfriends hanging around all the time, especially using the pool would be a bonus.
I only had one concern.
I had just started crossdressing for about a year before he moved in, mostly every weekend. By that time, I was dressing all out. Hair, make-up, boobs, nails, sexy outfits, etc. None of my family and friends knew about Robin, and (except for a couple times camming online) no one had ever seen me dressed up. So, I figured I would have to cut way back on my playtime. Having such a large house with my master bedroom at the far end of the house, I thought I could still safely dress every now and then until he went back to school in three months.
Or so I thought....
About three to four weeks after he moved in, I was all dressed up on a Friday night chatting and camming online. Around 2am, I heard him drive up and come inside. If he came home alone, he would just go to his end of the house. Usually, we would not see each other until morning. This time I heard him mess around in the kitchen for a few minutes, then total silence.
Soon I could hear him again, figuring he was going to his end of the house.
Suddenly, he knocks on my bedroom door. Now I go into full panic mode because I am completely dressed! Hair, make-up, nails, etc. I was wearing a tight black bodycon mini dress, my size D boobs with matching bra and lace thong panties. I finished off the look with thigh-high lace top stockings and black six-inch heels.
There is no way I can get undressed quickly. I am thinking if I do not answer he will go away. I am not that lucky! He knocks again, a little louder.
With my hands and knees shaking, I walk up and ask him through the door what he wants.
He replies, "Let me in, I know what you are doing".
As you can imagine I was speechless. All these thoughts of being busted raced through my head. It seemed like time stood still as I struggled to come up with some kind of response. Resigning to my fate of finally being busted, I said "Wait 30 seconds and then come in". I then turned off the overhead light, unlocked the door and jumped into bed. In my high heels and dress and covered up head to toe.
He opened the door and walked in. Taking a few seconds for his eyes to adjust, he looks at me and smiles. Seeing me all covered up he says, "You don't have to cover up, as a matter of fact get up and let me take a good look at you".
I am thinking, "Oh my god". But I moved the covers off and stood up. After I pulled my dress back down, I slowly walked over and stood just a few feet from him.
He said, "Wow you look great!". "Turn around for me". I do as he asks. Surprised that I have not tripped and fallen! Lol. I am in serious sensory overload. I have no idea what is going to happen.
I can feel that he has moved up right behind me. When his hands touch my hips, it is like an electric shock over my whole body. His face nuzzles into my hair and neck.
"Oh, you smell so good".
One of his hands glides up to my boobs, while the other slides down and stops just at the bottom of my dress. He plays with my stocking top for a second then slides up and encounters my bare cheek.
"You are so soft and smooth, I've got to see this". Gently he pushes me forward until I am at the end of the bed.
"Bend over the bed and spread your legs a little more."
He pulls my dress up to my waist and really starts feeling my cheeks. As I am trying not to moan like a slut, he says "This is going to be so much fun tonight!".
Standing me up and turning me back around forcefully. He pulls me in tight and gives me a very passionate kiss. After we break apart from that, he steps back and starts taking off his clothes. As I am watching him do that, I finally say something, asking him how he knew.
He said, “Well two ways, the first thing I noticed was lipstick-stained cigarettes in the ashtray on the back deck and last weekend I parked down the street and peeked in your bedroom window.”
I said, “You watched me through the window?”
He said, “Oh yes, for about an hour and I almost snuck in when you left your bedroom door open! I wanted to come in and just fuck the hell out of you. I was not sure how you would react, so I chickened out. Tonight, I peeked in again and saw you dressed all sexy again. Also, I noticed you were watching CD's getting fucked porn, so I knew you would be okay”.
About the time he finished talking, I noticed he only had his boxers on. There was a huge bulge in them. He caught me staring and laughed saying "You're going to take those off for me".
It just seemed natural to get on my knees as I took a few deep breaths. I was just inches away from seeing and touching my first cock.
My first hard cock.
A cock that I made hard.
Slowly I pulled his boxers down and yes. His cock sprang up and hit my chin!
It was about seven to eight inches long. He was also uncircumcised. The tip was very small to start but his whole cock grew very wide after the head.
Reaching out, I gently wrapped my hand around his cock. It felt so hard and yet soft at the same time. After a few seconds of staring at it, I started kissing and licking the head. Hearing him moan made me put more and more in my mouth. I had worked up to having six inches of cock in my mouth, when he put his hands on my head and started moving his cock in and out. Besides choking and gagging a few times, I held up well.
His thrusts and moans got faster, and I knew he was close to cumming. Just as I thought he was going to cum in mouth, he stopped. Pulling his cock out of my mouth, he looked down at me.
He said, "I do not want to cum yet, I've got other plans".
Looking right into my eyes he asked, "Besides those toys I saw you playing with last week, you're a virgin, aren't you?"
I said, "Yes I am."
He started laughing a little and said, "I'm going to enjoy fucking the hell out of you!"
He helped me up and guided me towards the bed. My four-poster bed is about waist high. Perfect height for him to bend me over.
Getting behind me, he lifted my dress over my butt.
At this point, I had so many thoughts and feelings going through my head I could barely speak. My hands and legs were shaking. When he started to rub his cock up and down between my cheeks, I squeaked out, "There is some lube on the nightstand".
When he got back, my thong panties were just pulled to the side. I looked back and saw him pouring the lube on his cock, then all over my butt. The feeling of him gently trying to get his cock in me was almost indescribable. He would just barely get the tip in, and then pull it out. This went on for a good five minutes. Soon, I noticed that I was pushing back, trying to get it in.
He said, "Okay, I think your tight little pussy is ready". I felt the tip go in again, but this time he kept a slow and steady push in me. The next thing I remember is when I felt his hips against my butt.
He said, "Oh my God you are so tight".
I think I babbled incoherently as he began slowly fucking me with long deep strokes.
I held on for dear life as he started going faster and faster. My clearest memory was hearing our bodies slapping together. Also, I remember him saying things to me. Like, "Do you like that cock?" and "You're a good slut". But all that paled in comparison when he yelled out, "I'm cumming" as he went as deep as he could and just held it there. I could feel his cock pulse over and over unloading his cum in me. He collapsed on my back, and we lay there for at least ten minutes.
Standing up behind me he gave me a light spank on the butt and started to pull it out. It was then that I realized how deep it was in me and how much cum there was. Cum started running down both of my legs.
I laughingly said, "I have to go clean up!".
That is when he replied, "Oh no! I am going to use that as lube in a few minutes".
He did me two more times that night, in every position he could think of.
We got together every weekend until he went back to school.
Looking back, I am glad it happened this way. It did wonders for my confidence. It would have taken me two years plus to get up the nerve to have my first date.
A good-looking college kid? 25+ years younger and he kept coming back for more? Wow! I started going out dressed in public (nighttime, lol!) on dates.
About our third time together, he told me about two of his friends (his age). They had talked about me and wanted to join us. However, they lived in town, and I knew them from the bar. It would have been too risky.
I ran into him and his girlfriend the following summer at that same bar (I was not dressed). We all talked like normal until she went to the bathroom. Very quietly he asked me if I was still dressing.
I’m sure I turned beet red as I just nodded my head.
He said, “I sure would love to see you again sometime. You are a great piece of ass! “
I almost spit up my beer when he said that! Lol!
I told him I still had the same number and he knew my schedule.
We saw his girlfriend coming back to rejoin us, and soon after they left.
Overall, I’m glad he caught me. It turned out perfectly!
PS: He texted me the following Friday night…….
8 months ago
