Sad Perv rsquo s 1st Times
- 2 years ago
- 139
- 0
First Times A Charm... My 1st Love. free porn video
It was late August 2002. I was 21, and looking for a room to rent getting out of Baltimore to broaden my horizons. I wanted to start fresh with maybe some new friends, and seek new ambitions. My folks had split up, after a nasty divorce, so I had to get my head clear. I was an only c***d, and was very close to them except now I seemed to be estranged to the both of them. So, after picking up the Sun paper, I browsed the "shared housing" section. I called, and talked to a few people. Some for one reason or another didn't really fit my fancy. One woman I talked to had a whole laundry list of restrictions including a curfew. I responded to an ad for a country home in Mt Airy. After calling, and speaking with a lively, friendly old fella.. I learned he was a manager of a credit union in Baltimore, and owns an estate on an old farm! He is just really looking for a room mate to add life to the place, and for company. Fine with me. So, we set up a time. I worked in a place called Columbia. It was an equal commute, save for less traffic and more highway time. The house was spacious. It was a very large rancher about a quarter mile off rural road 27. 5 bedrooms to be exact, and seperate three car garage filled with just "stuff". The inside definately looked like a bachelor pad. Nothing fancy, and he was somewhat of a pack rat. He was very jovial, talkative, and friendly. He gave me a tour, offered me a beer, and showed me all around. He had a library porn collection. He seemed very proud of it. I had also learned he had never been married, so he was also a life bachelor. He was 61, tall and thin. Wore glasses, and bald with a mustach. His motto was "women, you can't live with 'em, and you can't live without 'em". He also went on to tell me how all his friends had lost all they worked hard for. I felt comfortable so we talked about house rules, and monthly rate. We both agreed, and shook hands.
A couple of months go by, and we got along very well. Shared stories bullshitting late, and became pretty good pals. I started noticing him disappearing to one bedroom that was his office or "computer room".. He kept it locked all the time. I was really curious, so I started listening, and paying more attention. He would go in for 2-4 hours a night, and was pretty sure he was masturbating. I don't just assume things like that of people, but I heard him pant and groan. On a Monday while he was at work, I was off. I went through his keys, and tried them. They didn't work. So I looked through the kitchen drawers and found a lone door key, so I tried it, and viola! It worked! I walked in, and looked around. More porn. Lotion on the desk, and dried cum on the carpet. I giggled a little bit. I glanced through the magazines. Normal penthouse, leg world, juggs, etc. Now, the DVDs, and VHS vids were different. These were majority TS/TG/CD. My heart hit the floor. My adrenaline raced. I've been crossdressing since I was twelve. I have deeply wanted to belong to a man since puberty. I was so turned on I was shaking. I have a wardrobe of women's clothes in my storage unit that I've collected from thrift stores every year around Halloween. OMG!!! What am I going to do? I started thinking of him this way, now I admit he's very cute! OMG! If I say something to him, he'll know I've snooped! Wait! I ran to the rest of the porn stuff in his living room, in the video cassette rack, and saw! A few transgender videos! Yes! Now I know he won't suspect me of snooping. I called work, marked off for tomorrow, and went to my storage unit with a trash bag. I picked out a matching brown maxi skirt, & blazer, a pair of brown high heel pumps, an ivory blouse, and taupe pantyhose. I then drove to Baltimore where I found a wig shop. It was early October so I told the Chinese ladies I was shopping early for Halloween. They were very helpful, so I picked out a brown wig with auburn streaks. It was verrrry sexy! It complimented my face perfectly! I then drove to Sally Beauty supply down the road, and bought my eye makeup, foundation, blush, a few lip glosses, nails, and several shades of nail polish colors. My theme for tonight is brown. So the dark lip gloss gave me an almost gothic look, but very classy. So I went home, and fully exfoliated for my presentation.
I know this really sounds silly, but there's a song I always wanted to play when I lost my virginity to a man. It was the song Amazing by Aerosmith. It says much to me and my inner struggles of being a crossdresser. As well as fantasizing sex with a man for the first time. Anyhow, tonight was going to go good, or really, really bad. I got dressed, put on my makeup, filed, and painted my toes, and put on my nails. I was done by 3:00p, and looked better than I ever have. I was really kind of exhausted, and drained so I decided to take a nap, and unwind. I locked my bedroom door, and fell asleep. I woke at 9:30p. I tiptoed to the door, and unlocked it, opened it slowly, and saw all the lights were out except in the computer room where the light was on. My heart started racing. I turned to the mirror, reapplied my lip gloss, and makeup, straightened my hair up. I went to put on my pantyhose, and decided to leave them off. My toenails looked so good long, squared out, and painted a creamy mauve. I put on my 5" pointy dark brown stilettos that showed toe cleavage. Even better! I noticed my legs looked great, milky white, smooth as creamy silk by themselves. I started down the hallway. My shoes were very loud! He scrambled to the door, and opened it with his upper half of his body around the corner. I just said "Hi". He looked me up, and down slack jawed. My heart felt like it was going to explode, or I was going to faint. I broke the ice, and said.... Well this is me, this is what I do! I noticed you have videos of crossdressers so I thought why not, you must be an expert, right? He said... My god. You are just beautiful. Your the most beautiful creature I've ever seen! I giggled and said, I was hoping so. I really like you a lot. I did this for you. He stepped from behind the door into the hallway, revealing below his t-shirt he had a really mean erection poking his underwear. He was apparently masturbating in there. He flipped on the hallway light, and said " wow". Turn around. He walked up and carresed my smooth legs, and grabbed my butt. He said I love those shoes on you. He laughed. He slapped my butt. I reached down and felt his dick. It was huge! It was very long and thick. I couldn't wrap my hand totally around it. I said can I help you with this? He said I'd love that! He dipped in and kissed me forcefully. His tongue filling my mouth, it felt so strange a bristled face against mine. I came out for air. He said, would you like to come to my bedroom? I said trying to catch my breath.. Yes, please! But first, this is my first time! There's something I want to do! I want to play a song. I told him about my request he laughed and said yes! Of course! I teetered in my heels downt the hall to my room to get my portable stereo, and he hollered down the hall.. I've got a CD player in my alarm clock.. So I grabbed my Aerosmith CD. I strutted swinging my hips down the hallway to his room. He was naked lighting candles all around the room. I loaded the cd, and skipped to "amazing", the pressed the repeat button. He turned the lights off, and walked to me at the foot of the bed, and lip locked with me again. My head was still raised to him even though I had five inch stilettos on. I felt his raging hard on pressed against my belly. He was grabbing my ass as we kissed rolling my skirt up feeling my asshole with his middle finger. I croutched down and started sucking his dick. His precum tasted so good. He was 8-1/2 inches long, and was hurting my jaw. I stood back up, dropped my skirt, said Fuck Me! Please Fuck Me!!! He grabbed his tub of Vaseline and sat me on the bed. I laid back. I said, get in here and lay down. He did. I then lubed him up, then myself. I threw my legs over his chest and lowered my ass to his cock. Put a dab into my hole. I dropped my bootie right down. It hurt for a slit second then felt like heaven. Up and down I went. I worked my hips front to back he felt so amazing! I heard the song and worked my hips back and forth taking it all in. This is everything I hoped it to be and more. I looked down at him and his facial expression was pure bliss. The music was going faster, and everything was so perfect. The song played over and over throughout the night. We had sex in every position the way a man and woman would. He came in me several times. He called out work the next day, and we christened every single room in the house. My bootie felt funny without him pumping me. By the weekend he proposed me quitting my job. I told him no, I have bills and a car payment. He protested not to worry. I really didn't feel right as I'm just that independent. He convinced me otherwise. So, six months later one of the bedrooms was a walk in closet. The words "I Love You" were rolling off each others tongues. I had begun hormone therapy. We cleaned up his house and we made it a beautiful home. By a year, I was absolutely passable. We were madly in love with each other. Never fought or argued once. I never missed my life as a male, or looked back. Shortly after, I had started a new job at a bank, as "Linda". Frank and I were together almost three years as a couple. Sadly he suffered a massive stroke, and passed away shortly after. His family (nieces and nephews/ brother and two sisters) tried their best to make things awkward for me. If I had not met Frank, maybe they had been successful. He nurtured me emotionally to be who I am. I don't mean ashamed either.
A couple of months go by, and we got along very well. Shared stories bullshitting late, and became pretty good pals. I started noticing him disappearing to one bedroom that was his office or "computer room".. He kept it locked all the time. I was really curious, so I started listening, and paying more attention. He would go in for 2-4 hours a night, and was pretty sure he was masturbating. I don't just assume things like that of people, but I heard him pant and groan. On a Monday while he was at work, I was off. I went through his keys, and tried them. They didn't work. So I looked through the kitchen drawers and found a lone door key, so I tried it, and viola! It worked! I walked in, and looked around. More porn. Lotion on the desk, and dried cum on the carpet. I giggled a little bit. I glanced through the magazines. Normal penthouse, leg world, juggs, etc. Now, the DVDs, and VHS vids were different. These were majority TS/TG/CD. My heart hit the floor. My adrenaline raced. I've been crossdressing since I was twelve. I have deeply wanted to belong to a man since puberty. I was so turned on I was shaking. I have a wardrobe of women's clothes in my storage unit that I've collected from thrift stores every year around Halloween. OMG!!! What am I going to do? I started thinking of him this way, now I admit he's very cute! OMG! If I say something to him, he'll know I've snooped! Wait! I ran to the rest of the porn stuff in his living room, in the video cassette rack, and saw! A few transgender videos! Yes! Now I know he won't suspect me of snooping. I called work, marked off for tomorrow, and went to my storage unit with a trash bag. I picked out a matching brown maxi skirt, & blazer, a pair of brown high heel pumps, an ivory blouse, and taupe pantyhose. I then drove to Baltimore where I found a wig shop. It was early October so I told the Chinese ladies I was shopping early for Halloween. They were very helpful, so I picked out a brown wig with auburn streaks. It was verrrry sexy! It complimented my face perfectly! I then drove to Sally Beauty supply down the road, and bought my eye makeup, foundation, blush, a few lip glosses, nails, and several shades of nail polish colors. My theme for tonight is brown. So the dark lip gloss gave me an almost gothic look, but very classy. So I went home, and fully exfoliated for my presentation.
I know this really sounds silly, but there's a song I always wanted to play when I lost my virginity to a man. It was the song Amazing by Aerosmith. It says much to me and my inner struggles of being a crossdresser. As well as fantasizing sex with a man for the first time. Anyhow, tonight was going to go good, or really, really bad. I got dressed, put on my makeup, filed, and painted my toes, and put on my nails. I was done by 3:00p, and looked better than I ever have. I was really kind of exhausted, and drained so I decided to take a nap, and unwind. I locked my bedroom door, and fell asleep. I woke at 9:30p. I tiptoed to the door, and unlocked it, opened it slowly, and saw all the lights were out except in the computer room where the light was on. My heart started racing. I turned to the mirror, reapplied my lip gloss, and makeup, straightened my hair up. I went to put on my pantyhose, and decided to leave them off. My toenails looked so good long, squared out, and painted a creamy mauve. I put on my 5" pointy dark brown stilettos that showed toe cleavage. Even better! I noticed my legs looked great, milky white, smooth as creamy silk by themselves. I started down the hallway. My shoes were very loud! He scrambled to the door, and opened it with his upper half of his body around the corner. I just said "Hi". He looked me up, and down slack jawed. My heart felt like it was going to explode, or I was going to faint. I broke the ice, and said.... Well this is me, this is what I do! I noticed you have videos of crossdressers so I thought why not, you must be an expert, right? He said... My god. You are just beautiful. Your the most beautiful creature I've ever seen! I giggled and said, I was hoping so. I really like you a lot. I did this for you. He stepped from behind the door into the hallway, revealing below his t-shirt he had a really mean erection poking his underwear. He was apparently masturbating in there. He flipped on the hallway light, and said " wow". Turn around. He walked up and carresed my smooth legs, and grabbed my butt. He said I love those shoes on you. He laughed. He slapped my butt. I reached down and felt his dick. It was huge! It was very long and thick. I couldn't wrap my hand totally around it. I said can I help you with this? He said I'd love that! He dipped in and kissed me forcefully. His tongue filling my mouth, it felt so strange a bristled face against mine. I came out for air. He said, would you like to come to my bedroom? I said trying to catch my breath.. Yes, please! But first, this is my first time! There's something I want to do! I want to play a song. I told him about my request he laughed and said yes! Of course! I teetered in my heels downt the hall to my room to get my portable stereo, and he hollered down the hall.. I've got a CD player in my alarm clock.. So I grabbed my Aerosmith CD. I strutted swinging my hips down the hallway to his room. He was naked lighting candles all around the room. I loaded the cd, and skipped to "amazing", the pressed the repeat button. He turned the lights off, and walked to me at the foot of the bed, and lip locked with me again. My head was still raised to him even though I had five inch stilettos on. I felt his raging hard on pressed against my belly. He was grabbing my ass as we kissed rolling my skirt up feeling my asshole with his middle finger. I croutched down and started sucking his dick. His precum tasted so good. He was 8-1/2 inches long, and was hurting my jaw. I stood back up, dropped my skirt, said Fuck Me! Please Fuck Me!!! He grabbed his tub of Vaseline and sat me on the bed. I laid back. I said, get in here and lay down. He did. I then lubed him up, then myself. I threw my legs over his chest and lowered my ass to his cock. Put a dab into my hole. I dropped my bootie right down. It hurt for a slit second then felt like heaven. Up and down I went. I worked my hips front to back he felt so amazing! I heard the song and worked my hips back and forth taking it all in. This is everything I hoped it to be and more. I looked down at him and his facial expression was pure bliss. The music was going faster, and everything was so perfect. The song played over and over throughout the night. We had sex in every position the way a man and woman would. He came in me several times. He called out work the next day, and we christened every single room in the house. My bootie felt funny without him pumping me. By the weekend he proposed me quitting my job. I told him no, I have bills and a car payment. He protested not to worry. I really didn't feel right as I'm just that independent. He convinced me otherwise. So, six months later one of the bedrooms was a walk in closet. The words "I Love You" were rolling off each others tongues. I had begun hormone therapy. We cleaned up his house and we made it a beautiful home. By a year, I was absolutely passable. We were madly in love with each other. Never fought or argued once. I never missed my life as a male, or looked back. Shortly after, I had started a new job at a bank, as "Linda". Frank and I were together almost three years as a couple. Sadly he suffered a massive stroke, and passed away shortly after. His family (nieces and nephews/ brother and two sisters) tried their best to make things awkward for me. If I had not met Frank, maybe they had been successful. He nurtured me emotionally to be who I am. I don't mean ashamed either.
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