Random Stories Where I Get Fucked, Number 1.
My first Blog post was autobiographical, and historical, since it detailed my beginnings as a crossdresser. For the next few entries, I'm going to just post random experiences I've had in my adventures as a Sissy Slut. These are not in any chronological order. The incident which I'm going to write about in this entry happened around 2002-03, and is also autobiographical.
I have had good luck with Adult Friend Finder and its allied sites. This is not a commercial for them, they have flaws and grub for money just like everyone does, but back in the early 2000's, when I was just beginning to become very active as the aforedescribed Sissy Slut, that group of sites sort of dominated the online hookup field.
I was contacted by a man who said that he lived in Chicago, traveled frequently to Pittsburgh and Cleveland, and could be available for hookups at hotels near the major airports for those cities. He wrote a nice, literate introductory note, without using any street slang, sounded like he was intelligent and interesting, and sent me face pix without any reluctance. Since I live about sixty miles from each of those air terminals this was basically a doable concept for me. and I sort of liked the idea of meeting a man for a sexual liaison at his hotel room. For some reason the concept appealed to me, and I have to admit I thought of myself as being similar to the characters played by Liz Taylor in Butterfield 8, or Jane Fonda in Klute. So, I agreed that it would be fun to meet, and, if we liked each other, have hookup sex the next time he traveled.
We corresponded infrequently over the next few weeks, but kept the possibility of meeting open, and after about a month give-or-take he said that he would be in Cleveland on business the next week, and would be staying at a Marriott hotel off Chagrin Boulevard for three nights. My schedule was open for that period, and we set a date.
Now, as I wrote above, this story is not in chronological order, but it did occur fairly early in my career of bed-hopping, and I was a bit nervous about driving sixty miles to meet a stranger with the express idea that I was going to be fucked if things went well. I was, therefore, a bit apprehensive as well as quite pleased when I got an email with the news that he had arrived at his hotel. We exchanged emails to arrange a specific time, which if I recall correctly was sometime around nine o' clock, and he gave me the room number, which was not at the Marriott. He told me that there were other executives from his company who were with him, and he had gotten a room down the road in order that his comings and goings should not be observed. (pun intended)
It's not easy for a Gurl to get ready for a date, by the way. The first part of the process to douche so that no nasty fecal material is going to make the sex sordid, and the second is shaving and applying lotion all over to have smooth and sexy-soft skin. Then comes the hard part, making up a masculine face so that it looks as feminine as possible, and that takes about an hour depending on how motivated I am. Anyway, I completed the process, and as best I can remember wore a denim skirt, a turtle-neck sweater, tights, and tassel loafers, complete with suitable accessories on the drive to the motel which took a bit over an hour. It was early/mid autumn, and I was trying to blend, which is my aim always when I go out in public. I packed a small carry-on size luggage bag with man clothes in case the worst happened on the trip, and also so that I'd look like just another traveler in the hotel's lobby.
The highway drive went without incident, I breezed through the lobby without a problem, and rode the elevator up to the proper floor, but nonetheless it was with more than a modicum of nervousness that I knocked on the door. I wasn't sure whether I was going to meet the sane businessman who had been corresponding with me, or a weirdo who was going to open the door nude with an erection and a handkerchief dosed with chrloroform. When door opened I was in fact surprised and a bit spooked because he was a giant! Literally! He was six and a half feet tall, weighed over three hundred pounds, and not much of it was fat hanging around his waist. I knew that he was tall, his height was on his online profile, but I hadn't expected his girth and massiveness.
To condense the story a bit, he greeted me pleasantly, a bit shyly even, and after I had recovered my mental equilibrium I accepted a brief kiss on the lips, to which I responded a bit shyly myself, and entered the room. He said his name was Walt, and he said had a bottle of wine, Merlot which is my favorite, and we sat, sipped wine, and chatted for a while. It turned out that he had played on the offensive line for a Big Ten university, had a tryout in the NFL but failed to make the final roster cut, had gotten a starter job with the company for which he worked through a football booster's influence, and had made the most of it. I told him how I had gotten started crossdressing as we worked our way thru the wine, and after a while he put his hand on my thigh and started to pull me closer to him. I certainly had no intention to resist, and before long we were French-kissing, and my motor was running at high speed. He was wearing a pair of cargo shorts, leather sandals, and an oxford shirt, and before he could even think about asking, I had his fly open and my hand inside his shorts. When I could feel him responding, I told him to take the shorts off, and sit back down, and I then spread his legs apart and slid onto my knees before him. After I had sucked and licked on his cock until it was hard, he asked me to take off my clothes, and I stripped down until only my bra and breast forms remained. I had brought a pair of thigh-highs and four-inch patent leather pumps in my travel-bag, and put them on as elaborately and sexily as I could in front of him, and then resumed my oral worship on the bed.
At this juncture, for those who are curious, Walt is not enormously endowed, he is proportionate. So, if a man who is 5-10 or 6-0 has a six inch cock then his is probably about seven inches, and thick to scale, but not John Holmes mammoth. This was fine by me, I had by this time learned that I really enjoyed sucking cock, but on the other hand, I have no desire to get myself a trans-mandibular-joint dislocation by trying to set a world's size record.
After a while, Walt lay back on the bed, and, after I put a condom on him and applied some lube to each of us, I sat down on his cock. It had been a while since I'd been with a man, so I went slow, and I remember that if felt good, and at the same time I was still in a bit of physical awe of the sheer size of his body. After a while we got into a rhythm, and were going pretty good when I felt him tense-up, without any warning, and I knew that he had cum. He had only lasted for two minutes or so, and he was a bit embarrassed, and I confess that I was a bit disappointed, because it seemed like a long drive for only that short amount of time. I rolled off him, removed the condom and tied a knot in it, and lay next to him, trying to figure out how long I should stay before leaving if he didn't make a first move.
I was surprised a bit, but not shocked, when within a minute or two he began to play with my cockette. When he began to suck on me it was a familiar pattern of behavior, so I just laid back and enjoyed his attentions. He started to get worked-up again as I got more erect, and he asked me to fuck him. This wasn't exactly in the contract of employment for Liz Taylor or Jane Fonda type call girls, so I said that I wasn't sure, but he sort of insisted, and said that he had toys which would help loosen him. So, to condense, about ten minutes later I was behind him as he did the traditional ass-up and face-in-the-pillow posture which is usually my standard position. I don't know how it happened, but I got a marvelous hard-on, and fucked him bareback for several minutes before I pulled-out and ejaculated on his perineum and scrotum.
So, at this juncture, I was fairly exhausted, and to my total delight, Walt rolled over, grabbed me in his massive arms and sort of growled, "Now I'm going to fuck you right! The way a man should fuck a sissy!" So, practically before I knew what was happening, I had a three hundred pound man on top of me, my ankles spread in his hands, and his cock inside me for the second time within an hour. It was like being on a really wild roller coaster, the kind that sort of throws you around and there's nothing you can do to stop the action, all you can do is hang-on and survive until the end of the ride. And, it was an enjoyable ride, skinny guys have great hip action, but a man with a big ass and big thighs can deliver power thrusts which make a gurl feel it in every inch of her body. Because this was his second cum of the night, it took Walt a while to reach his climax and I no longer had any regrets about doing the long drive. I remember after a while squealing every time his thrusts drove into me, and he told me that made him hump me even harder! He came inside me, which was an unplanned risk, but it happens when two people get too involved in the heat of the moment.
Afterwards we both lay in the bed for a while, I don't know how long, but 20-30 minutes, and then Walt got out of the bed, went into the bathroom to clean-up, and then got dressed. He said that he had to get back to his business hotel room to spend the night, but said that I could stay as long as I liked. He gave me a quick kiss, very sweet, and left. I lay in bed for a while longer, and then went into the bathroom where he had left me an envelope with a hundred dollar bill and a note. It said that he knew that I romanticized about Butterfield 8 and Klute, and that this would make the experience more authentic. The first and only time I've ever been paid, even if it was an insider joke really.
We met at least a dozen more times over the intervening years, but around 2012, I remember it was during the second Obama campaign, he took a different job with a company located in Sacramento, and no longer travels to the midwest. Too bad, because as I have learned over the years, it's difficult to find a good guy who's also a good fuck, and Walt is one of the best!
I have had good luck with Adult Friend Finder and its allied sites. This is not a commercial for them, they have flaws and grub for money just like everyone does, but back in the early 2000's, when I was just beginning to become very active as the aforedescribed Sissy Slut, that group of sites sort of dominated the online hookup field.
I was contacted by a man who said that he lived in Chicago, traveled frequently to Pittsburgh and Cleveland, and could be available for hookups at hotels near the major airports for those cities. He wrote a nice, literate introductory note, without using any street slang, sounded like he was intelligent and interesting, and sent me face pix without any reluctance. Since I live about sixty miles from each of those air terminals this was basically a doable concept for me. and I sort of liked the idea of meeting a man for a sexual liaison at his hotel room. For some reason the concept appealed to me, and I have to admit I thought of myself as being similar to the characters played by Liz Taylor in Butterfield 8, or Jane Fonda in Klute. So, I agreed that it would be fun to meet, and, if we liked each other, have hookup sex the next time he traveled.
We corresponded infrequently over the next few weeks, but kept the possibility of meeting open, and after about a month give-or-take he said that he would be in Cleveland on business the next week, and would be staying at a Marriott hotel off Chagrin Boulevard for three nights. My schedule was open for that period, and we set a date.
Now, as I wrote above, this story is not in chronological order, but it did occur fairly early in my career of bed-hopping, and I was a bit nervous about driving sixty miles to meet a stranger with the express idea that I was going to be fucked if things went well. I was, therefore, a bit apprehensive as well as quite pleased when I got an email with the news that he had arrived at his hotel. We exchanged emails to arrange a specific time, which if I recall correctly was sometime around nine o' clock, and he gave me the room number, which was not at the Marriott. He told me that there were other executives from his company who were with him, and he had gotten a room down the road in order that his comings and goings should not be observed. (pun intended)
It's not easy for a Gurl to get ready for a date, by the way. The first part of the process to douche so that no nasty fecal material is going to make the sex sordid, and the second is shaving and applying lotion all over to have smooth and sexy-soft skin. Then comes the hard part, making up a masculine face so that it looks as feminine as possible, and that takes about an hour depending on how motivated I am. Anyway, I completed the process, and as best I can remember wore a denim skirt, a turtle-neck sweater, tights, and tassel loafers, complete with suitable accessories on the drive to the motel which took a bit over an hour. It was early/mid autumn, and I was trying to blend, which is my aim always when I go out in public. I packed a small carry-on size luggage bag with man clothes in case the worst happened on the trip, and also so that I'd look like just another traveler in the hotel's lobby.
The highway drive went without incident, I breezed through the lobby without a problem, and rode the elevator up to the proper floor, but nonetheless it was with more than a modicum of nervousness that I knocked on the door. I wasn't sure whether I was going to meet the sane businessman who had been corresponding with me, or a weirdo who was going to open the door nude with an erection and a handkerchief dosed with chrloroform. When door opened I was in fact surprised and a bit spooked because he was a giant! Literally! He was six and a half feet tall, weighed over three hundred pounds, and not much of it was fat hanging around his waist. I knew that he was tall, his height was on his online profile, but I hadn't expected his girth and massiveness.
To condense the story a bit, he greeted me pleasantly, a bit shyly even, and after I had recovered my mental equilibrium I accepted a brief kiss on the lips, to which I responded a bit shyly myself, and entered the room. He said his name was Walt, and he said had a bottle of wine, Merlot which is my favorite, and we sat, sipped wine, and chatted for a while. It turned out that he had played on the offensive line for a Big Ten university, had a tryout in the NFL but failed to make the final roster cut, had gotten a starter job with the company for which he worked through a football booster's influence, and had made the most of it. I told him how I had gotten started crossdressing as we worked our way thru the wine, and after a while he put his hand on my thigh and started to pull me closer to him. I certainly had no intention to resist, and before long we were French-kissing, and my motor was running at high speed. He was wearing a pair of cargo shorts, leather sandals, and an oxford shirt, and before he could even think about asking, I had his fly open and my hand inside his shorts. When I could feel him responding, I told him to take the shorts off, and sit back down, and I then spread his legs apart and slid onto my knees before him. After I had sucked and licked on his cock until it was hard, he asked me to take off my clothes, and I stripped down until only my bra and breast forms remained. I had brought a pair of thigh-highs and four-inch patent leather pumps in my travel-bag, and put them on as elaborately and sexily as I could in front of him, and then resumed my oral worship on the bed.
At this juncture, for those who are curious, Walt is not enormously endowed, he is proportionate. So, if a man who is 5-10 or 6-0 has a six inch cock then his is probably about seven inches, and thick to scale, but not John Holmes mammoth. This was fine by me, I had by this time learned that I really enjoyed sucking cock, but on the other hand, I have no desire to get myself a trans-mandibular-joint dislocation by trying to set a world's size record.
After a while, Walt lay back on the bed, and, after I put a condom on him and applied some lube to each of us, I sat down on his cock. It had been a while since I'd been with a man, so I went slow, and I remember that if felt good, and at the same time I was still in a bit of physical awe of the sheer size of his body. After a while we got into a rhythm, and were going pretty good when I felt him tense-up, without any warning, and I knew that he had cum. He had only lasted for two minutes or so, and he was a bit embarrassed, and I confess that I was a bit disappointed, because it seemed like a long drive for only that short amount of time. I rolled off him, removed the condom and tied a knot in it, and lay next to him, trying to figure out how long I should stay before leaving if he didn't make a first move.
I was surprised a bit, but not shocked, when within a minute or two he began to play with my cockette. When he began to suck on me it was a familiar pattern of behavior, so I just laid back and enjoyed his attentions. He started to get worked-up again as I got more erect, and he asked me to fuck him. This wasn't exactly in the contract of employment for Liz Taylor or Jane Fonda type call girls, so I said that I wasn't sure, but he sort of insisted, and said that he had toys which would help loosen him. So, to condense, about ten minutes later I was behind him as he did the traditional ass-up and face-in-the-pillow posture which is usually my standard position. I don't know how it happened, but I got a marvelous hard-on, and fucked him bareback for several minutes before I pulled-out and ejaculated on his perineum and scrotum.
So, at this juncture, I was fairly exhausted, and to my total delight, Walt rolled over, grabbed me in his massive arms and sort of growled, "Now I'm going to fuck you right! The way a man should fuck a sissy!" So, practically before I knew what was happening, I had a three hundred pound man on top of me, my ankles spread in his hands, and his cock inside me for the second time within an hour. It was like being on a really wild roller coaster, the kind that sort of throws you around and there's nothing you can do to stop the action, all you can do is hang-on and survive until the end of the ride. And, it was an enjoyable ride, skinny guys have great hip action, but a man with a big ass and big thighs can deliver power thrusts which make a gurl feel it in every inch of her body. Because this was his second cum of the night, it took Walt a while to reach his climax and I no longer had any regrets about doing the long drive. I remember after a while squealing every time his thrusts drove into me, and he told me that made him hump me even harder! He came inside me, which was an unplanned risk, but it happens when two people get too involved in the heat of the moment.
Afterwards we both lay in the bed for a while, I don't know how long, but 20-30 minutes, and then Walt got out of the bed, went into the bathroom to clean-up, and then got dressed. He said that he had to get back to his business hotel room to spend the night, but said that I could stay as long as I liked. He gave me a quick kiss, very sweet, and left. I lay in bed for a while longer, and then went into the bathroom where he had left me an envelope with a hundred dollar bill and a note. It said that he knew that I romanticized about Butterfield 8 and Klute, and that this would make the experience more authentic. The first and only time I've ever been paid, even if it was an insider joke really.
We met at least a dozen more times over the intervening years, but around 2012, I remember it was during the second Obama campaign, he took a different job with a company located in Sacramento, and no longer travels to the midwest. Too bad, because as I have learned over the years, it's difficult to find a good guy who's also a good fuck, and Walt is one of the best!
7 years ago
glad you liked it! 
