Crossing the Line
- 3 years ago
- 23
- 0
Crossing A Different Line free porn video
In my personal journey from straight, married heterosexual to bi male, I discovered, along the way, that I was aroused by women’s lingerie. It started with trying on a pair of my wife’s nylon panties. The feel of the silky material, and the sight of how it fit, quickly brought on an erection. I used another silky pair in my hand to jack myself off, being careful not to get any cum on the panties. The orgasm was unusually powerful.
In the weeks following, I pursued my new found curiosity, particularly with my eighteen year-old stepdaughter’s underwear. Looking through her dirty clothes hamper, I was surprised by the amount of erotic underwear she wore, ranging from tiny bikinis to V-string thongs. Besides trying them on myself, I also slipped them over my head with the stained, crusted crotch over my mouth and nose. I would masturbate as I enjoyed the musty scent and tasted the dried vaginal secretions - once again resulting in strong orgasms.
I had not previously spent much time looking at pictures or adult videos of cross-dressed males. However, as I explored my growing interest in lingerie, I found myself growing more and more aroused by crossdressing and shemale porn. These soon became a regular part of my frequent masturbation fantasies.
I eventually acquired a small (carefully hidden) wardrobe of my own erotic things, including thongs, boyshorts, stockings, bras, breast forms, miniskirts, and camisoles. Whenever I was able to have some private time by myself (like on business trips), I would dress up and enjoy the look and feel of the sexy lingerie. I rounded out my assortment with high heels and wigs. With a slim build, I actually considered myself rather attractive when dressed as a woman. I even adopted a female persona by the name of Mona.
Not surprisingly, it was difficult to reconcile my interests in such things with my normal life. Those who knew me would have regarded me as an upright family man, respected in both my profession and at church. No one would have ever guessed that I harbored such a secret.
It was as if I had developed a Jekyll and Hyde personality. To those around me, I was a straight-as-an-arrow family guy. But, when I dressed as Mona, I was a different person entirely. I was a wanton and lustful woman, who wanted to be taken and ravished by a manly suitor. I longed to be the submissive object of pleasure for a strong, well-endowed, long-lasting male with an insatiable sexual appetite.
Of course, lacking a real male partner, I resorted to the next available thing, which usually took the form of a large cock dildo. While dressed as Mona, I impaled myself fully and repeatedly on an over-sized dildo, moaning loudly and begging my imaginary lover to fuck me. I would continue the deep prostate stimulation until I would experience a hands-free orgasm.
These virtual reality dressing sessions continued from time to time until I attended an out-of-town retreat for company executives in Atlanta. I had some free time after dinner, so one evening I went to a nearby upscale theater that featured adult films, among others. I was feeling adventurous, so I left a small sticky note in a stall of the men’s restroom with my phone number and interests (bi-male CD). I don’t know what came over me, as I would not normally do something so risky.
I honestly didn’t expect an answer, much less from someone whom I would consider a suitable partner. So, I was surprised (and cautiously thrilled) when I received a call in my hotel room from a guy who had seen my note. I was relieved to learn that is was not the theater management, calling to complain about the note. Rather, it was an articulate guy with a mid-Eastern accent. I briefly explained my interests, and invited him to come by my room. He replied that he had never been with a CD but that he was nonetheless interested. He accepted my invitation without further hesitation.
I prepared and dressed in my finest and sexiest black lingerie outfit in anticipation of his arrival, getting squeaky clean and primping to make myself as attractive and alluring as possible. Otherwise, I was a nervous wreck. My heart was pounding, and my hands were clammy. I had never been with a man while dressed as a female.
The knock at the door came after what seemed an eternity, and upon opening it, I was greeted by a distinguished-looking gentleman wearing a very expensive suit. I invited him in and welcomed him, introducing myself as Mona. He told me a little about himself, not taking his eyes off of me. He was a business executive in town for a client meeting. I guessed he was in his mid-forties with black hair, mustache, dark complexion, and stout build. Clearly of mid-Eastern descent.
The first move is always awkward, so I walked by him, over to the bed, gently touching his crotch as I passed. Once on the bed, I lay back, assumed a seductive pose and suggested he get more comfortable. He began removing his coat and tie, then unbuttoned his shirt. As he was doing so, I sat up on the bed in front of him and unbuckled his trousers and fly, dropping his pants to the floor.
I was very pleased at what I saw - a very prominent bulge in the front of tight, stretchy undershorts. I looked up and teasingly stroked it, causing it to grow to the extent that it could no longer be contained under the fabric. The bulbous head was exposed. I leaned forward and licked it, then hooked my fingers in his waistband and pulled down, releasing the magnificent organ.
It was all I could have dreamed of - big and hard, with a large, flanged head and pronounced veins running down the shaft. I took as much of it into my eager mouth as I could. Only about half! From the sounds of his response, mumbling in a foreign language, he was enjoying it. I looked up and ran my hands over his furry solid chest as I continued sucking. He was so manly, so desirable.
He lifted me up and led me over to the sofa. He sat down and reclined against the back, motioning for me to approach. I climbed onto the sofa, straddling him with my knees on either side against the back, my feet on the seat. He pulled my panties down. Then, reaching around with his hands on my ass, pulled me into his face. He took my cock (which was tiny in comparison to his) between his lips.
I moaned as I felt his hot mouth engulf my hardness. The feel of his heavy mustache against my pubic area added to the erotic sensations. As he sucked, I felt a hand slip down to my shaved furrow. I gasped as his finger teased my puckered rosebud, then slipped inside my pre-lubed hole. I expressed my pleasure as explicitly as I could and encouraged him to continue - not that he needed to be urged on. I was very glad that he accepted, and wanted, that part of me. It left me free to be the woman I desired to be.
He pushed me away, slowly lowering me to his lap until my knees rested on the seat on either side of him. Our eyes locked once again as I continued to lower myself. I felt his engorged knob, now slippery with precum, moving back and forth over my hungry orifice. I had no condom, but I was so aroused at the thought of being taken as a woman, I didn’t care. As I sat down, my anal sphincter yielded and he slipped inside, burrowing into my eager cavity and eliciting a load moan from me. My head tilted back and my eyes closed as I bottomed out on his lap, fully impaled on his rigid man-pole.
After a moment of adjusting to his girth, we began to move together. I raised myself up and down, sliding against his masculine chest. On each down stroke he would lift his hips to meet me, so as to bury himself completely in me. The pleasure of being filled by him was so intense that I could not keep quiet, even if I wanted to. I moaned and cried out with every deep penetration of his magnificent procreative organ. I was responding as a submissive female, and I wanted him to impregnate me with his thick fluid.
I would have been happy to continue this indefinitely, but he had other ideas. He pushed me up and slid out from under me, still leaving me on my knees on the seat of the sofa facing the back. He stood behind me and lifted my miniskirt to expose my smooth ass. It was at just the right level for being taken again.
It was at this point, when I turned my head back to look at him, that I noticed I had not drawn the window drapes. They were more than half open. We were on the ground floor, so we were visible to any outside onlooker, even in the subdued light. However, I didn’t have time to change the situation. He grasped my hips and drove his bare, mid-Eastern cock deep into me in one powerful thrust.
I cried out in ecstasy as he violated me from behind with unbridled animal passion. His hips slammed against my smooth feminine ass, and his heavy, virile ballsack slapped my shaved furrow with each wonderful thrust. He worked his hard muscle like a powerful piston, driving relentlessly against my sensitive male P-spot. He brought me to new heights of pleasure as I played the part of a woman in heat.
I was soon racked by a powerful anal orgasm. It caused my ring of rectal muscles to constrict around his throbbing member in uncontrollable spasms. Strands of semen splattered across the sofa as my cock swung back and forth. This brought him over the edge too. He pulled me against him in one final thrust and held me tight as his cock erupted inside me, filling me with his hot foreign seed.
He stayed embedded in me until his ejaculations subsided. Then he slipped out. I tightened my anus, wanting to retain his cum. (I was sure I was gaping after such a pounding.) I sat down on the sofa in front of him, looked up, and took his ass-fresh cock into my mouth. I carefully cleaned him of any residue from our copulation.
While he dressed, he asked me if I had occasion to be in Atlanta very often. I answered that, regretfully, I was rarely in town for an overnight stay like this. Following this, he thanked me with a manly hug, and left. I cleaned up both myself and the sofa, still feeling the lingering aftereffects of the anal assault.
By now, it was getting late and I needed to call home to check in with my wife before she went to bed. As we caught up on the day’s activities (well, not every activity), my thoughts drifted to what had just taken place. It dawned on me that I had crossed yet another line in my personal journey of sexual self-discovery. It was the beginning of a new chapter, and I couldn’t go back.
In the weeks following, I pursued my new found curiosity, particularly with my eighteen year-old stepdaughter’s underwear. Looking through her dirty clothes hamper, I was surprised by the amount of erotic underwear she wore, ranging from tiny bikinis to V-string thongs. Besides trying them on myself, I also slipped them over my head with the stained, crusted crotch over my mouth and nose. I would masturbate as I enjoyed the musty scent and tasted the dried vaginal secretions - once again resulting in strong orgasms.
I had not previously spent much time looking at pictures or adult videos of cross-dressed males. However, as I explored my growing interest in lingerie, I found myself growing more and more aroused by crossdressing and shemale porn. These soon became a regular part of my frequent masturbation fantasies.
I eventually acquired a small (carefully hidden) wardrobe of my own erotic things, including thongs, boyshorts, stockings, bras, breast forms, miniskirts, and camisoles. Whenever I was able to have some private time by myself (like on business trips), I would dress up and enjoy the look and feel of the sexy lingerie. I rounded out my assortment with high heels and wigs. With a slim build, I actually considered myself rather attractive when dressed as a woman. I even adopted a female persona by the name of Mona.
Not surprisingly, it was difficult to reconcile my interests in such things with my normal life. Those who knew me would have regarded me as an upright family man, respected in both my profession and at church. No one would have ever guessed that I harbored such a secret.
It was as if I had developed a Jekyll and Hyde personality. To those around me, I was a straight-as-an-arrow family guy. But, when I dressed as Mona, I was a different person entirely. I was a wanton and lustful woman, who wanted to be taken and ravished by a manly suitor. I longed to be the submissive object of pleasure for a strong, well-endowed, long-lasting male with an insatiable sexual appetite.
Of course, lacking a real male partner, I resorted to the next available thing, which usually took the form of a large cock dildo. While dressed as Mona, I impaled myself fully and repeatedly on an over-sized dildo, moaning loudly and begging my imaginary lover to fuck me. I would continue the deep prostate stimulation until I would experience a hands-free orgasm.
These virtual reality dressing sessions continued from time to time until I attended an out-of-town retreat for company executives in Atlanta. I had some free time after dinner, so one evening I went to a nearby upscale theater that featured adult films, among others. I was feeling adventurous, so I left a small sticky note in a stall of the men’s restroom with my phone number and interests (bi-male CD). I don’t know what came over me, as I would not normally do something so risky.
I honestly didn’t expect an answer, much less from someone whom I would consider a suitable partner. So, I was surprised (and cautiously thrilled) when I received a call in my hotel room from a guy who had seen my note. I was relieved to learn that is was not the theater management, calling to complain about the note. Rather, it was an articulate guy with a mid-Eastern accent. I briefly explained my interests, and invited him to come by my room. He replied that he had never been with a CD but that he was nonetheless interested. He accepted my invitation without further hesitation.
I prepared and dressed in my finest and sexiest black lingerie outfit in anticipation of his arrival, getting squeaky clean and primping to make myself as attractive and alluring as possible. Otherwise, I was a nervous wreck. My heart was pounding, and my hands were clammy. I had never been with a man while dressed as a female.
The knock at the door came after what seemed an eternity, and upon opening it, I was greeted by a distinguished-looking gentleman wearing a very expensive suit. I invited him in and welcomed him, introducing myself as Mona. He told me a little about himself, not taking his eyes off of me. He was a business executive in town for a client meeting. I guessed he was in his mid-forties with black hair, mustache, dark complexion, and stout build. Clearly of mid-Eastern descent.
The first move is always awkward, so I walked by him, over to the bed, gently touching his crotch as I passed. Once on the bed, I lay back, assumed a seductive pose and suggested he get more comfortable. He began removing his coat and tie, then unbuttoned his shirt. As he was doing so, I sat up on the bed in front of him and unbuckled his trousers and fly, dropping his pants to the floor.
I was very pleased at what I saw - a very prominent bulge in the front of tight, stretchy undershorts. I looked up and teasingly stroked it, causing it to grow to the extent that it could no longer be contained under the fabric. The bulbous head was exposed. I leaned forward and licked it, then hooked my fingers in his waistband and pulled down, releasing the magnificent organ.
It was all I could have dreamed of - big and hard, with a large, flanged head and pronounced veins running down the shaft. I took as much of it into my eager mouth as I could. Only about half! From the sounds of his response, mumbling in a foreign language, he was enjoying it. I looked up and ran my hands over his furry solid chest as I continued sucking. He was so manly, so desirable.
He lifted me up and led me over to the sofa. He sat down and reclined against the back, motioning for me to approach. I climbed onto the sofa, straddling him with my knees on either side against the back, my feet on the seat. He pulled my panties down. Then, reaching around with his hands on my ass, pulled me into his face. He took my cock (which was tiny in comparison to his) between his lips.
I moaned as I felt his hot mouth engulf my hardness. The feel of his heavy mustache against my pubic area added to the erotic sensations. As he sucked, I felt a hand slip down to my shaved furrow. I gasped as his finger teased my puckered rosebud, then slipped inside my pre-lubed hole. I expressed my pleasure as explicitly as I could and encouraged him to continue - not that he needed to be urged on. I was very glad that he accepted, and wanted, that part of me. It left me free to be the woman I desired to be.
He pushed me away, slowly lowering me to his lap until my knees rested on the seat on either side of him. Our eyes locked once again as I continued to lower myself. I felt his engorged knob, now slippery with precum, moving back and forth over my hungry orifice. I had no condom, but I was so aroused at the thought of being taken as a woman, I didn’t care. As I sat down, my anal sphincter yielded and he slipped inside, burrowing into my eager cavity and eliciting a load moan from me. My head tilted back and my eyes closed as I bottomed out on his lap, fully impaled on his rigid man-pole.
After a moment of adjusting to his girth, we began to move together. I raised myself up and down, sliding against his masculine chest. On each down stroke he would lift his hips to meet me, so as to bury himself completely in me. The pleasure of being filled by him was so intense that I could not keep quiet, even if I wanted to. I moaned and cried out with every deep penetration of his magnificent procreative organ. I was responding as a submissive female, and I wanted him to impregnate me with his thick fluid.
I would have been happy to continue this indefinitely, but he had other ideas. He pushed me up and slid out from under me, still leaving me on my knees on the seat of the sofa facing the back. He stood behind me and lifted my miniskirt to expose my smooth ass. It was at just the right level for being taken again.
It was at this point, when I turned my head back to look at him, that I noticed I had not drawn the window drapes. They were more than half open. We were on the ground floor, so we were visible to any outside onlooker, even in the subdued light. However, I didn’t have time to change the situation. He grasped my hips and drove his bare, mid-Eastern cock deep into me in one powerful thrust.
I cried out in ecstasy as he violated me from behind with unbridled animal passion. His hips slammed against my smooth feminine ass, and his heavy, virile ballsack slapped my shaved furrow with each wonderful thrust. He worked his hard muscle like a powerful piston, driving relentlessly against my sensitive male P-spot. He brought me to new heights of pleasure as I played the part of a woman in heat.
I was soon racked by a powerful anal orgasm. It caused my ring of rectal muscles to constrict around his throbbing member in uncontrollable spasms. Strands of semen splattered across the sofa as my cock swung back and forth. This brought him over the edge too. He pulled me against him in one final thrust and held me tight as his cock erupted inside me, filling me with his hot foreign seed.
He stayed embedded in me until his ejaculations subsided. Then he slipped out. I tightened my anus, wanting to retain his cum. (I was sure I was gaping after such a pounding.) I sat down on the sofa in front of him, looked up, and took his ass-fresh cock into my mouth. I carefully cleaned him of any residue from our copulation.
While he dressed, he asked me if I had occasion to be in Atlanta very often. I answered that, regretfully, I was rarely in town for an overnight stay like this. Following this, he thanked me with a manly hug, and left. I cleaned up both myself and the sofa, still feeling the lingering aftereffects of the anal assault.
By now, it was getting late and I needed to call home to check in with my wife before she went to bed. As we caught up on the day’s activities (well, not every activity), my thoughts drifted to what had just taken place. It dawned on me that I had crossed yet another line in my personal journey of sexual self-discovery. It was the beginning of a new chapter, and I couldn’t go back.
Dottie
- 29.04.2021
- 23
- 0
- Category:
- Crossdressing
