A Different Sort Of Straight Roommate Story
By my mid 30s I had completely come to terms with my sexuality. While probably not what most would consider 'gay', I wasn't exactly 'straight' either. I'd discovered that I could usually enjoy whatever was between my partner's legs, provided they were clean and hygienic.
I'd dated a number of folks who fell in-between the stereotypical male and female roles. Whatever the term at the time was, I've heard them all: crossdresser, drag queen, transvestite, transsexual, tranny, whatever. Like I said, I was happily attracted to whomever and have been told that I'm an excellent partner.
I'd met a gal (crossdresser, tranny, whatever term was big at the time) named Leza. In honesty, we met while I was on a date with a friend of hers (who was also in the same category). The three of us had a few drinks and conversation one night at the bar. As Leza was leaving earlier than we'd planned to, I offered to walk her to her car. Another friend in the bar suggested I stay with my date and offered to walk her instead. Seemed all well and good to me, right?
A couple days later, I'd been chatting online with Leza and she made it clear that she'd really wanted me to walk her to her car. She'd wanted to give me a blowjob. Oh My! Once again, my inability to sense when someone is attracted to me ruined yet another opportunity. Before I sound like a bad guy, the gal I was on a date with...it wasn't anything serious for either of us. We dated off/on for a while. She dated others. I dated others. We just occasionally enjoyed each other's company.
Back to Leza: she was (and still is) quite attractive! Dark skinned, great body, pretty face, big smile, and a great geeky sense of humor. She looks better in a short skirt than most. All the right curves in all the right places. Now knowing that she found me attractive, I had to figure out a way to make this happen. Problem...she had a sorta common-law wife. Not officially married but I wasn't thrilled on stepping into that situation. But...we all sometimes do things we probably shouldn't.
Around this time, my best friend was going through divorce #2. I'd suggested he stay at my house as it was halfway between his job and his now-former house where his soon-to-be ex and k**s were staying. It worked out great for the most part. I was on the road a lot for work, so it was nice to know the house wasn't sitting empty. He helped with the bills and at one point insisted on a satellite dish. I'm no fan of television but I went along with it. Actually started watching a few shows...but grew bored of them quickly.
Sharing my house with my best friend was pretty great. We hung out when we felt like it, went out to bars, partied, all the usual stuff. But we also led our own lives. He'd go spend time with his k**s, date a bit, typical guy-going-through-a-divorce stuff. We didn't really have any kind of schedule. If one of us had a guest, the other tended to be a good host about it. In short, we stayed out of each other's way. He knew that I wasn't technically 'straight'...but I don't think he'd ever thought much about it or had really witnessed any sort of non-straight behavior. Until one day....
I was a dull, gray afternoon. I'd taken the day off and was just hanging around the house. I ended up chatting with Leza, who had also taken the day. She was 'dressed' (just to clarify, she lived and worked in guy mode) and asked if I'd be up for some company. She knew I was a photographer on the side and was curious to see some of my work. The roomie was at work, so I invited her on over.
The afternoon tended to be memorable for a number of reasons. For starters, Leza was looking extra fine! I won't lie, I was in ultra dorky flirt mode from the second she walked in the door. I'd blown my chance once...wasn't going to happen again should it arise. She'd brought along a gym bag...apparently filled with her guy clothes, so she could change before going home. This didn't strike me as unusual at all.
We went into my den and I pulled up some of my folders of photography. She was really enjoying it. She pulled her chair in good and close...you know, for a better view. She asked about some of my more private, erotic, shots. Could she see some of them? Once I explained that they were private, and not for public consumption or discussion, and that was made clear, I showed her a few. She knew a face or two. She was moving in closer for an even better view, and I suggested she might as well just sit on my lap. I told you I was in ultra dorky flirt mode. She just gave me 'a look' and hopped on my lap. It was probably pretty obvious that I was excited. As memory serves, it was obvious that she was too. One couldn't help but notice.
No surprises here, we started kissing and groping...same as most of you have probably done with someone at some point. We made our way from the chair, to the floor, to the recliner, back to the floor, to the couch, eaching losing more and more bits of clothing along the way. We never heard the front door open.
Hearing something in the den, my roommate stopped by the doorway to say "Hi". He was greeted by the sight of Leza on all fours with my face buried in her gorgeous, round, dark ass. I believe what he heard was her moaning. As she told me later, I was making her eyes roll back in her head and making her head spin. Roomie's "Hi" morphed into a "Whoops!'
I paused for a moment and said "Hey, this is Leza! Say HI Leza!" Leza gave a little wave and moaned a hello. Roomie went upstairs to his room and Leza and I went back to the task at hand. I won't bore you with the details. I will say her cock was a lot larger than I expected and her oral skills still, years later, remain in my top 3 of all time.
After we were spent and finished, Leza asked if she could use my bathroom to clean up. I pointed the way, went upstairs to grab a robe and came back downstairs. A few minutes later, the roomie came downstairs. I guess he'd figured we were finished and he wouldn't be blinded by the sights of me and a friend having fun.
I went back to the bathroom to check on Leza. She had cleaned up...cleaned up so much that she was no longer Leza. She was now Walt. I told her she still looked hot and that if Walt ever wanted to visit, that too would be fine.
On the way out, I made sure to stop and introduce my roomie, again. "Say Hi to Walt!" I suggested. Roomie did and when Walt returned the greeting...roomie recognized the voice from earlier. The look on his face was priceless!
A little while after my guest left, roomie asked me "Um, does that happen often?"
My answer was simple: "Not as often as I'd like."
OK...really, what did you expect for free?
I'd dated a number of folks who fell in-between the stereotypical male and female roles. Whatever the term at the time was, I've heard them all: crossdresser, drag queen, transvestite, transsexual, tranny, whatever. Like I said, I was happily attracted to whomever and have been told that I'm an excellent partner.
I'd met a gal (crossdresser, tranny, whatever term was big at the time) named Leza. In honesty, we met while I was on a date with a friend of hers (who was also in the same category). The three of us had a few drinks and conversation one night at the bar. As Leza was leaving earlier than we'd planned to, I offered to walk her to her car. Another friend in the bar suggested I stay with my date and offered to walk her instead. Seemed all well and good to me, right?
A couple days later, I'd been chatting online with Leza and she made it clear that she'd really wanted me to walk her to her car. She'd wanted to give me a blowjob. Oh My! Once again, my inability to sense when someone is attracted to me ruined yet another opportunity. Before I sound like a bad guy, the gal I was on a date with...it wasn't anything serious for either of us. We dated off/on for a while. She dated others. I dated others. We just occasionally enjoyed each other's company.
Back to Leza: she was (and still is) quite attractive! Dark skinned, great body, pretty face, big smile, and a great geeky sense of humor. She looks better in a short skirt than most. All the right curves in all the right places. Now knowing that she found me attractive, I had to figure out a way to make this happen. Problem...she had a sorta common-law wife. Not officially married but I wasn't thrilled on stepping into that situation. But...we all sometimes do things we probably shouldn't.
Around this time, my best friend was going through divorce #2. I'd suggested he stay at my house as it was halfway between his job and his now-former house where his soon-to-be ex and k**s were staying. It worked out great for the most part. I was on the road a lot for work, so it was nice to know the house wasn't sitting empty. He helped with the bills and at one point insisted on a satellite dish. I'm no fan of television but I went along with it. Actually started watching a few shows...but grew bored of them quickly.
Sharing my house with my best friend was pretty great. We hung out when we felt like it, went out to bars, partied, all the usual stuff. But we also led our own lives. He'd go spend time with his k**s, date a bit, typical guy-going-through-a-divorce stuff. We didn't really have any kind of schedule. If one of us had a guest, the other tended to be a good host about it. In short, we stayed out of each other's way. He knew that I wasn't technically 'straight'...but I don't think he'd ever thought much about it or had really witnessed any sort of non-straight behavior. Until one day....
I was a dull, gray afternoon. I'd taken the day off and was just hanging around the house. I ended up chatting with Leza, who had also taken the day. She was 'dressed' (just to clarify, she lived and worked in guy mode) and asked if I'd be up for some company. She knew I was a photographer on the side and was curious to see some of my work. The roomie was at work, so I invited her on over.
The afternoon tended to be memorable for a number of reasons. For starters, Leza was looking extra fine! I won't lie, I was in ultra dorky flirt mode from the second she walked in the door. I'd blown my chance once...wasn't going to happen again should it arise. She'd brought along a gym bag...apparently filled with her guy clothes, so she could change before going home. This didn't strike me as unusual at all.
We went into my den and I pulled up some of my folders of photography. She was really enjoying it. She pulled her chair in good and close...you know, for a better view. She asked about some of my more private, erotic, shots. Could she see some of them? Once I explained that they were private, and not for public consumption or discussion, and that was made clear, I showed her a few. She knew a face or two. She was moving in closer for an even better view, and I suggested she might as well just sit on my lap. I told you I was in ultra dorky flirt mode. She just gave me 'a look' and hopped on my lap. It was probably pretty obvious that I was excited. As memory serves, it was obvious that she was too. One couldn't help but notice.
No surprises here, we started kissing and groping...same as most of you have probably done with someone at some point. We made our way from the chair, to the floor, to the recliner, back to the floor, to the couch, eaching losing more and more bits of clothing along the way. We never heard the front door open.
Hearing something in the den, my roommate stopped by the doorway to say "Hi". He was greeted by the sight of Leza on all fours with my face buried in her gorgeous, round, dark ass. I believe what he heard was her moaning. As she told me later, I was making her eyes roll back in her head and making her head spin. Roomie's "Hi" morphed into a "Whoops!'
I paused for a moment and said "Hey, this is Leza! Say HI Leza!" Leza gave a little wave and moaned a hello. Roomie went upstairs to his room and Leza and I went back to the task at hand. I won't bore you with the details. I will say her cock was a lot larger than I expected and her oral skills still, years later, remain in my top 3 of all time.
After we were spent and finished, Leza asked if she could use my bathroom to clean up. I pointed the way, went upstairs to grab a robe and came back downstairs. A few minutes later, the roomie came downstairs. I guess he'd figured we were finished and he wouldn't be blinded by the sights of me and a friend having fun.
I went back to the bathroom to check on Leza. She had cleaned up...cleaned up so much that she was no longer Leza. She was now Walt. I told her she still looked hot and that if Walt ever wanted to visit, that too would be fine.
On the way out, I made sure to stop and introduce my roomie, again. "Say Hi to Walt!" I suggested. Roomie did and when Walt returned the greeting...roomie recognized the voice from earlier. The look on his face was priceless!
A little while after my guest left, roomie asked me "Um, does that happen often?"
My answer was simple: "Not as often as I'd like."
OK...really, what did you expect for free?
4 年 前
