I had help along the journey...
I’ve had help along the way…
It took me a long time to realize that I was a sissy, or even what that was, and even longer to embrace it. My feelings switched back and forth over the years not really understanding what all those desires were and what they meant to me. Fortunately I’ve had some help along the way – some intended and some not.
My first recollection of being interested in my femininity was when I was much younger. Like many of us I discovered the joy of wearing girls clothes from my older sister who would dress me up like her little doll. I loved the way it made me feel, and believe it created the environment for me to love and cherish the feeling of being guided by loving, older women. As I got older that turned into a number of wonderful relationships with Mistresses who helped shape me. This story is about one of those chance relationships.
I was 37 and to the outside world I was your typical successful male. I was married with two kids and had all the benefits that life could offer. Inside though there were intense feelings that had been struggling to get out and be recognized. I tried to get my wife to explore that side of myself to no avail, so my sissy exploration took place when I could find some time to myself at home or at work. I would do all the things that closet sissies do in private – dress up in pretty lingerie and dresses, dream of being with someone who could accept me for who I was, and hooking up with women and other crossdressers online and on the telephone to help satisfy my deepest sexual desires. The advent of the Internet was a miracle to those of us who had no other outlet. It not only allowed us to express our true feelings, but it was also a world where we discovered how many others there were out there who felt the same or a similar way. It allowed me to better understand that sensual and sexual desires were not this or that, but rather a broad kaleidoscope of many different possibilities.
My office at work, after everyone would leave, was always a safe space that I could be alone to do what I wanted without being discovered. I would close the doors, get dressed, surf the web, talk on the phone, and play as I desired while drifting away from my real life. One afternoon after everyone had left I began the ritual that I so desired whenever the opportunity presented itself. I had all the time I needed. I got dressed in a very sexy, black lace lingerie outfit and made a phone call to my favorite 800 number “friend.”
Lisa knew me all too well and could always read in my voice what kind of mood I was in and what I needed. She had a sexy sultry voice, and would take her time guiding me through exploring myself and different sexual fantasies. Lisa was my first experience of having a Mistress, and she was the one who helped me discover my sissy name – Danielle. We had been talking about 30 minutes that day and I was getting slowly worked up into a deep sexual frenzy. I was on the gray, carpeted floor sitting with my legs beneath me all dressed except for my panties, which were lying by my side at that point. I was slowly raising and lowering my hips on and off of the dildo that was penetrating me. My cock was dripping and Lisa would have me gently run my finger over the tip and then take my finger and slowly lick the sweetness into my mouth. I vividly recall the sunlight streaming through the windows and seeing the dust particles in the sun beams and the glitter of the strands of precum as they stretched from my cock to my mouth. It was quite mesmerizing, beautiful, and sensually complete.
Lisa was expert at bringing me to peak and then backing me off. She would do that over and over again until I earned the release that I so needed. Lisa allowed me to pick up the pace with my self-penetration, but denied me several more times until I begged for her permission. At last I heard her sultry voice express the words that I had been waiting for almost an hour. As I thrust myself down on the dildo Lisa allowed me to touch myself and I exploded strands as I moaned like the sissy that I am. I felt completely satisfied in every way. My inner sensuality had been allowed to fully express and my sexual release had been complete. As I was coming out of the trance and back to my senses I looked up and saw my administrative assistant, Cathy, standing in the doorway.
I had no idea how long she had been there watching me. I probably should have been shocked or expressed some sort of regret, but I didn’t. I realized that I had literally just been caught with my pants down and for just that moment I felt strangely happy that I had just been outed. Cathy just looked at me on the floor dressed in lingerie and a blonde wig having just exhausted myself. She had an oddly serene look of calm on her face. We just gazed at each other for a bit, albeit my gaze a bit sheepish I think. Lisa’s voice registered back in my ear and I briefly told her that we had been unexpectedly interrupted. She just giggled and said, “Good luck with that. Talk with you soon, Danielle.”
Still having eye contact with Cathy, in that moment I really had no idea what to do. She walked slowly toward me, squatted down, and started to slowly caress the back of my head. I started to cry. She took me in her arms and I cried harder. All she said was, “It was beautiful watching you. I’d like you to tell me more about it sometime.” She kissed me on the forehead, got up, and left.
Sometime later I found out that Cathy had forgotten something when she left earlier that day and stopped back by the office to pick it up. She heard me moaning and poked her head in to see if everything was alright, only to find me in the throes of self-pleasure with Lisa on the phone. She had been watching for 10 or 15 minutes before Lisa had given me permission to cum and noticed she was there in the doorway. I remember that I wasn’t really embarrassed or anything, but rather was relieved for a brief period and then worried about how would this all turn out? What if she told others about this? Would I lose my job?
I was dreading going into the office the next day. When I arrived I wasn’t sure what to expect. To my surprise, and certainly my delight, Cathy was just normal. I was having some difficultly processing how she could have seen what she did and not behave somewhat differently, but she didn’t. As the day progressed I became more comfortable with the situation and her peace with it, and asked her if she had some time to discuss something in my office. She came in and sat with me and we talked for about two hours. I poured out my soul and told her everything – every little detail from my earliest recollections to my deepest desires and fantasies. She was wonderfully supportive and genuinely interested in all of it. When we were done talking she approached me, took me into her arms and asked me if I had any interest in exploring my feelings further, with her? I instinctively looked at her and just said, yes, I would love that very much.
I knew all of the potential pitfalls of a workplace relationship, particularly given that she worked for me. At that point in my life though I had buried all of my feelings inside of me and in that moment I felt like I was just going to explode if I didn’t share it with a real person in a face-to-face situation. I was tired of pretending and Cathy had just offered me a way out of all of that. I trusted her and taking the risk felt like it was worth it. As it turns out it was one of the best decisions of my life and was formative in helping me really discover who I was sexually and becoming and accepting myself.
Cathy turned out to be a natural Mistress. I never got the sense that she was just doing it for me. She really enjoyed it and loved the time we had together as much as I did. We shared all of our desires with each other and explored them over the next six months. Nothing was ignored; straight sex, oral sex, masturbation, pegging, anal for her, cum swapping, watching porn together, helping me dress, everything. And I loved it! My particular love, or perhaps lust, was to have her guide me through dressing and then masturbating while she watched or while I pleasured her with my tongue. She enjoyed that too and could tell how satisfied I would be all dolled up with my head buried between her legs running my hand up and down my throbbing clit. We loved to watch each other cum and she was the one who introduced me to and helped me with self-facials.
One day after work we had planned to meet. Cathy had instructed me to get dressed in some sexy lingerie beforehand. I spent a good amount of time picking out a cute, pink lace lingerie set. I had a pink silk Teddy on with a matching lace bra and crotchless panty set, pink thigh high stockings with bows at the top, a frilly pink choker with a little silver bell, pink nail polish, red lipstick, and a blonde wig on. I made sure I was sitting on the floor with my legs folded under me off to one side waiting for her arrival. I was hoping to be as sexy a little sissy as I possibly could be for her.
Cathy is smart and attractive, in her mid-40s. About 5’7” with a soft, medium build. She had shoulder length, brunette hair with hazel eyes, and full, soft lips. She always kidded me about how I like to wear more makeup than she does. Her skin was light, soft, and smooth and she had no need to cover or accentuate it. When she walked into my office that day she was wearing a white silk, button down blouse with a black skirt and black pumps. She gazed at me for a moment sitting on the floor, smiled and then approached me; squatting down and kissing me on the top of my head. “You look beautiful,” she said, “exactly what I was imagining, Danielle.” I just smiled and started to feel the warm, sensual sensations of her presence close to me.
She stood up and walked over to my desk and sat on the edge with her arms to her side and her legs dangling toward the floor. “Danielle, come here baby, and get me ready. Take my shoes off.” I crawled over toward her and gently caressed her legs while I removed both of her shoes. As I looked at up her she motioned for me to stand up and get close to her. She reached behind me and pulled me in as our lips met and our tongues danced in and out of each other’s mouths. Softly kissing and moaning Cathy unbuttoned her blouse and gently pushed my head down toward her puffy breasts still shrouded in a white bra. I reached behind her to undo the clasp and she removed it from under her blouse. I gently returned to her breasts with my mouth and hands and heard her moaning as I licked one and then the other.
Cathy spread her legs and gently pushed my head downward. I knew what she wanted, but heard her again say, “Danielle, get me ready.” I was on my knees at that point and lifted her skirt up a bit to expose her soft, shaven pussy glistening with moisture. My clit instinctively began to drip as I kissed the inside of her soft thighs and then met her lips with my tongue. We both moaned as my tongue and face darted up and down her wetness and her lips began to swell. “Danielle, now you need to get our friend ready,” she said. A bit bewildered by the request I looked up at her as she gestured behind me.
Standing behind me was a young, attractive young man who I had never seen before. He was looking at me with no particular expression on his face. “Get him ready, Danielle.” At first I wasn’t sure what she meant, but then I realized she wanted me get his cock ready. As I crawled toward him he unbuckled his belt, unzipped his pants, and let them drop to the floor. As I got closer he took off his briefs. Cathy had taken our exploration to a new level and I was about to make one of my deepest fantasies a reality. I took him first into my hand and then into my waiting mouth, slowly suckling and rubbing my tongue along the bottom of his shaft. As he grew in my mouth I could feel my clit pounding beneath me up into my stomach. His sweetness trickled into the back of my throat as he groaned. “That’s enough, Danielle.”
I withdrew his cock from my mouth and glanced over at Cathy sitting on the edge of the desk with her fingers running through her glistening slit. She motioned the young man toward her as she spread her legs. “Baby, you did a great job getting us ready. I want you to watch him fuck me now. Come closer to me and play with yourself, but don’t cum.”
As I crawled toward Cathy she pulled him closer and guided him to the entrance to her swollen pussy. I caressed Cathy’s legs as he pushed inside of her. I could hear them both groan as I watched as he at first slowly fucked her and then picked up the pace of his trusts. His cock sliding in and out of her pussy just inches from my face. One of my hands was rubbing Cathy’s legs as the other gently rubbed my swollen clit. Moving slowly so I didn’t bring myself to orgasm. Cathy’s and my eyes never lost contact as I watched her pleasure build. It took everything I had not to explode as their pace got faster and he gushed inside of her, both letting out primal sounds during what appeared to be coinciding orgasms. Not once during all of that did Cathy’s gaze escape from mine except for the brief periods when one of us closed our eyes in the mist of the pleasure we felt or an occasional glance at his cock sliding in and out of her.
When they were finished I was pent up beyond my limits. Cathy reached down and gently pushed my head around to her freshly fucked pussy. I began licking and sucking on her and taking all of the cum the both had created into my mouth. “Make me cum again, Danielle, and then you can release yourself sweet sissy.” It didn’t take long for Cathy to orgasm on my face as I devoured her. Her sounds of orgasm and deep convulsions were so sweet particularly knowing that I was the one causing them. As her shivers began to subside she pulled me up and toward her as tough she wanted me to enter her as well. I took my clit in my hand to guide it in, but she stopped me. “Just look in my eyes as you jerk yourself off onto my pussy, Danielle. I want to watch you cum while you pleasure yourself.” Cathy started to rub her wetness and pulled me in closer so I could feel her hand bringing herself pleasure on the tip of my clit while I gently stroked myself. As our breathing got heavier we stared into each other’s eyes and both achieved the release that we had been so desirous of. She gently kissed me then pushed me back down to my knees. As she spread her legs I could see our cum intertwined and I obediently licked and cleaned her up as she shuddered her wetness onto my waiting face one last time. I was in pure bliss.
Cathy and I had several more years of wonderful experiences and I will forever be grateful for her willingness and guidance in becoming the sissy that I am today. I will always love her for that.
It took me a long time to realize that I was a sissy, or even what that was, and even longer to embrace it. My feelings switched back and forth over the years not really understanding what all those desires were and what they meant to me. Fortunately I’ve had some help along the way – some intended and some not.
My first recollection of being interested in my femininity was when I was much younger. Like many of us I discovered the joy of wearing girls clothes from my older sister who would dress me up like her little doll. I loved the way it made me feel, and believe it created the environment for me to love and cherish the feeling of being guided by loving, older women. As I got older that turned into a number of wonderful relationships with Mistresses who helped shape me. This story is about one of those chance relationships.
I was 37 and to the outside world I was your typical successful male. I was married with two kids and had all the benefits that life could offer. Inside though there were intense feelings that had been struggling to get out and be recognized. I tried to get my wife to explore that side of myself to no avail, so my sissy exploration took place when I could find some time to myself at home or at work. I would do all the things that closet sissies do in private – dress up in pretty lingerie and dresses, dream of being with someone who could accept me for who I was, and hooking up with women and other crossdressers online and on the telephone to help satisfy my deepest sexual desires. The advent of the Internet was a miracle to those of us who had no other outlet. It not only allowed us to express our true feelings, but it was also a world where we discovered how many others there were out there who felt the same or a similar way. It allowed me to better understand that sensual and sexual desires were not this or that, but rather a broad kaleidoscope of many different possibilities.
My office at work, after everyone would leave, was always a safe space that I could be alone to do what I wanted without being discovered. I would close the doors, get dressed, surf the web, talk on the phone, and play as I desired while drifting away from my real life. One afternoon after everyone had left I began the ritual that I so desired whenever the opportunity presented itself. I had all the time I needed. I got dressed in a very sexy, black lace lingerie outfit and made a phone call to my favorite 800 number “friend.”
Lisa knew me all too well and could always read in my voice what kind of mood I was in and what I needed. She had a sexy sultry voice, and would take her time guiding me through exploring myself and different sexual fantasies. Lisa was my first experience of having a Mistress, and she was the one who helped me discover my sissy name – Danielle. We had been talking about 30 minutes that day and I was getting slowly worked up into a deep sexual frenzy. I was on the gray, carpeted floor sitting with my legs beneath me all dressed except for my panties, which were lying by my side at that point. I was slowly raising and lowering my hips on and off of the dildo that was penetrating me. My cock was dripping and Lisa would have me gently run my finger over the tip and then take my finger and slowly lick the sweetness into my mouth. I vividly recall the sunlight streaming through the windows and seeing the dust particles in the sun beams and the glitter of the strands of precum as they stretched from my cock to my mouth. It was quite mesmerizing, beautiful, and sensually complete.
Lisa was expert at bringing me to peak and then backing me off. She would do that over and over again until I earned the release that I so needed. Lisa allowed me to pick up the pace with my self-penetration, but denied me several more times until I begged for her permission. At last I heard her sultry voice express the words that I had been waiting for almost an hour. As I thrust myself down on the dildo Lisa allowed me to touch myself and I exploded strands as I moaned like the sissy that I am. I felt completely satisfied in every way. My inner sensuality had been allowed to fully express and my sexual release had been complete. As I was coming out of the trance and back to my senses I looked up and saw my administrative assistant, Cathy, standing in the doorway.
I had no idea how long she had been there watching me. I probably should have been shocked or expressed some sort of regret, but I didn’t. I realized that I had literally just been caught with my pants down and for just that moment I felt strangely happy that I had just been outed. Cathy just looked at me on the floor dressed in lingerie and a blonde wig having just exhausted myself. She had an oddly serene look of calm on her face. We just gazed at each other for a bit, albeit my gaze a bit sheepish I think. Lisa’s voice registered back in my ear and I briefly told her that we had been unexpectedly interrupted. She just giggled and said, “Good luck with that. Talk with you soon, Danielle.”
Still having eye contact with Cathy, in that moment I really had no idea what to do. She walked slowly toward me, squatted down, and started to slowly caress the back of my head. I started to cry. She took me in her arms and I cried harder. All she said was, “It was beautiful watching you. I’d like you to tell me more about it sometime.” She kissed me on the forehead, got up, and left.
Sometime later I found out that Cathy had forgotten something when she left earlier that day and stopped back by the office to pick it up. She heard me moaning and poked her head in to see if everything was alright, only to find me in the throes of self-pleasure with Lisa on the phone. She had been watching for 10 or 15 minutes before Lisa had given me permission to cum and noticed she was there in the doorway. I remember that I wasn’t really embarrassed or anything, but rather was relieved for a brief period and then worried about how would this all turn out? What if she told others about this? Would I lose my job?
I was dreading going into the office the next day. When I arrived I wasn’t sure what to expect. To my surprise, and certainly my delight, Cathy was just normal. I was having some difficultly processing how she could have seen what she did and not behave somewhat differently, but she didn’t. As the day progressed I became more comfortable with the situation and her peace with it, and asked her if she had some time to discuss something in my office. She came in and sat with me and we talked for about two hours. I poured out my soul and told her everything – every little detail from my earliest recollections to my deepest desires and fantasies. She was wonderfully supportive and genuinely interested in all of it. When we were done talking she approached me, took me into her arms and asked me if I had any interest in exploring my feelings further, with her? I instinctively looked at her and just said, yes, I would love that very much.
I knew all of the potential pitfalls of a workplace relationship, particularly given that she worked for me. At that point in my life though I had buried all of my feelings inside of me and in that moment I felt like I was just going to explode if I didn’t share it with a real person in a face-to-face situation. I was tired of pretending and Cathy had just offered me a way out of all of that. I trusted her and taking the risk felt like it was worth it. As it turns out it was one of the best decisions of my life and was formative in helping me really discover who I was sexually and becoming and accepting myself.
Cathy turned out to be a natural Mistress. I never got the sense that she was just doing it for me. She really enjoyed it and loved the time we had together as much as I did. We shared all of our desires with each other and explored them over the next six months. Nothing was ignored; straight sex, oral sex, masturbation, pegging, anal for her, cum swapping, watching porn together, helping me dress, everything. And I loved it! My particular love, or perhaps lust, was to have her guide me through dressing and then masturbating while she watched or while I pleasured her with my tongue. She enjoyed that too and could tell how satisfied I would be all dolled up with my head buried between her legs running my hand up and down my throbbing clit. We loved to watch each other cum and she was the one who introduced me to and helped me with self-facials.
One day after work we had planned to meet. Cathy had instructed me to get dressed in some sexy lingerie beforehand. I spent a good amount of time picking out a cute, pink lace lingerie set. I had a pink silk Teddy on with a matching lace bra and crotchless panty set, pink thigh high stockings with bows at the top, a frilly pink choker with a little silver bell, pink nail polish, red lipstick, and a blonde wig on. I made sure I was sitting on the floor with my legs folded under me off to one side waiting for her arrival. I was hoping to be as sexy a little sissy as I possibly could be for her.
Cathy is smart and attractive, in her mid-40s. About 5’7” with a soft, medium build. She had shoulder length, brunette hair with hazel eyes, and full, soft lips. She always kidded me about how I like to wear more makeup than she does. Her skin was light, soft, and smooth and she had no need to cover or accentuate it. When she walked into my office that day she was wearing a white silk, button down blouse with a black skirt and black pumps. She gazed at me for a moment sitting on the floor, smiled and then approached me; squatting down and kissing me on the top of my head. “You look beautiful,” she said, “exactly what I was imagining, Danielle.” I just smiled and started to feel the warm, sensual sensations of her presence close to me.
She stood up and walked over to my desk and sat on the edge with her arms to her side and her legs dangling toward the floor. “Danielle, come here baby, and get me ready. Take my shoes off.” I crawled over toward her and gently caressed her legs while I removed both of her shoes. As I looked at up her she motioned for me to stand up and get close to her. She reached behind me and pulled me in as our lips met and our tongues danced in and out of each other’s mouths. Softly kissing and moaning Cathy unbuttoned her blouse and gently pushed my head down toward her puffy breasts still shrouded in a white bra. I reached behind her to undo the clasp and she removed it from under her blouse. I gently returned to her breasts with my mouth and hands and heard her moaning as I licked one and then the other.
Cathy spread her legs and gently pushed my head downward. I knew what she wanted, but heard her again say, “Danielle, get me ready.” I was on my knees at that point and lifted her skirt up a bit to expose her soft, shaven pussy glistening with moisture. My clit instinctively began to drip as I kissed the inside of her soft thighs and then met her lips with my tongue. We both moaned as my tongue and face darted up and down her wetness and her lips began to swell. “Danielle, now you need to get our friend ready,” she said. A bit bewildered by the request I looked up at her as she gestured behind me.
Standing behind me was a young, attractive young man who I had never seen before. He was looking at me with no particular expression on his face. “Get him ready, Danielle.” At first I wasn’t sure what she meant, but then I realized she wanted me get his cock ready. As I crawled toward him he unbuckled his belt, unzipped his pants, and let them drop to the floor. As I got closer he took off his briefs. Cathy had taken our exploration to a new level and I was about to make one of my deepest fantasies a reality. I took him first into my hand and then into my waiting mouth, slowly suckling and rubbing my tongue along the bottom of his shaft. As he grew in my mouth I could feel my clit pounding beneath me up into my stomach. His sweetness trickled into the back of my throat as he groaned. “That’s enough, Danielle.”
I withdrew his cock from my mouth and glanced over at Cathy sitting on the edge of the desk with her fingers running through her glistening slit. She motioned the young man toward her as she spread her legs. “Baby, you did a great job getting us ready. I want you to watch him fuck me now. Come closer to me and play with yourself, but don’t cum.”
As I crawled toward Cathy she pulled him closer and guided him to the entrance to her swollen pussy. I caressed Cathy’s legs as he pushed inside of her. I could hear them both groan as I watched as he at first slowly fucked her and then picked up the pace of his trusts. His cock sliding in and out of her pussy just inches from my face. One of my hands was rubbing Cathy’s legs as the other gently rubbed my swollen clit. Moving slowly so I didn’t bring myself to orgasm. Cathy’s and my eyes never lost contact as I watched her pleasure build. It took everything I had not to explode as their pace got faster and he gushed inside of her, both letting out primal sounds during what appeared to be coinciding orgasms. Not once during all of that did Cathy’s gaze escape from mine except for the brief periods when one of us closed our eyes in the mist of the pleasure we felt or an occasional glance at his cock sliding in and out of her.
When they were finished I was pent up beyond my limits. Cathy reached down and gently pushed my head around to her freshly fucked pussy. I began licking and sucking on her and taking all of the cum the both had created into my mouth. “Make me cum again, Danielle, and then you can release yourself sweet sissy.” It didn’t take long for Cathy to orgasm on my face as I devoured her. Her sounds of orgasm and deep convulsions were so sweet particularly knowing that I was the one causing them. As her shivers began to subside she pulled me up and toward her as tough she wanted me to enter her as well. I took my clit in my hand to guide it in, but she stopped me. “Just look in my eyes as you jerk yourself off onto my pussy, Danielle. I want to watch you cum while you pleasure yourself.” Cathy started to rub her wetness and pulled me in closer so I could feel her hand bringing herself pleasure on the tip of my clit while I gently stroked myself. As our breathing got heavier we stared into each other’s eyes and both achieved the release that we had been so desirous of. She gently kissed me then pushed me back down to my knees. As she spread her legs I could see our cum intertwined and I obediently licked and cleaned her up as she shuddered her wetness onto my waiting face one last time. I was in pure bliss.
Cathy and I had several more years of wonderful experiences and I will forever be grateful for her willingness and guidance in becoming the sissy that I am today. I will always love her for that.
1年前
