I Finally Got Up The Nerve

by Diamond

© 2004

  

We met online. I had posted a free personal ad and he, "Jackie" wrote to me telling me that he liked the way I described myself and was interested in knowing more. Over the next few weeks we emailed sometimes as many as three times a day, often with pictures and always very descriptive. He knew I was new at this and very eager to meet. He was a beautiful tall crossdresser with incredible legs, ass and taste in clothing. He lived out of town but was coming to San Diego on business. He asked if there was any way I would come to his hotel room and spend some time together. My heart raced as I read that email a hundred times before writing back "yes!"

I was to arrive at 10:00am so we would have most of the day and afternoon together. I was to bring wine, candles and me, and he was going to set the mood just perfectly. I must have driven around the parking lot 5 or 6 times before telling myself that this was what I had always wanted. I literally spoke aloud as I drove, saying "I want to be here and I want to touch him."

I arrived at the hotel and called his room. My heart was racing and practically out of breath, with a small sports bag in one hand and an ear-to-ear grin on my face. He told me the room number and said that he would leave the door open. I knocked lightly, the door slowly moved backwards and I entered into a dimly lit room. The curtains were closed and blacked out the light of day. Only the candles burning on the dresser let me know I was in the right place. I walked in and the door closed behind me and could smell the perfume in the air. He welcomed me. He was standing right behind me. He told me to put the bag on the floor and stand right there.

I could barely move. He then stood behind me and I could feel the heat of his body near mine, his breath on my neck and his hands on my hips, slowly working their way around and squeezing my chest. He whispered in my ear how pleased he was that I had decided to show up. I mustered up all the energy I could just to respond and placed my hands on his hands, letting him know that I was pleased too. In our emails, I told him that if he was the first to initiate the kiss, I knew that I would simply melt into him. He slowly turned me around, backed me up against the door, placed one hand around my back and the other around my head and tortuously slowly moved his lips towards mine. First a peck, then another, then another, and then his tongue dared my lips to part. I took that dare and responded in kind. We were wrapped together in an incredible kiss. He took his hand from the back of my head and placed it on my hand, slowly guiding it across his body. He felt wonderful to me and I could not wait to continue. I placed both of my hands on his ass and pulled him close. We could feel each others excitement growing with the moment. Moments later, he broke the kiss, welcomed me once again and took my hand, leading me into the room. I opened the first bottle of wine and I offered a toast - "Here's to a beautiful day with a beautiful new friend." We kissed sharing a sip of wine between our mouths.

This was the first chance I had to see him. I looked around the room, noticing a nice nightstand and mirror, a few scattered pieces of lingerie hanging over a chair, and then back at him - white high heels, stockings, lace garter belt, matching thong panties, a beautiful bra filled out quiet nicely I might add, and a lace robe. He asked me if I liked what I saw and my only response was to put my glass down, hold him close and initiate the next kiss. He took my hand and slowly guided it up to his chest, then guided it down across his stomach and in between us. The time had come, and I was more than ready. I took a breath as we kissed and slowly let my fingers dance across his panties until I found him. I then pressed my palm firmly against him trying to see how big he was. This was my first cock and I was so aroused to have it in my hands.

We backed up towards the bed and I sat down, never letting go of him. "Do you like that?" he asked. Before I could answer he told me that I could kiss it if I wanted to and then he moved closer. I instinctively kissed him through the panties, holding him close with one hand and touching him with the other as I kissed up and down the shaft. He knew just what to say as he cooed and complimented me. He began to massage my shoulders and hold me closer. I peeled his panties down slowly and was now only inches away, and seconds away from kissing my first cock too. "Yes" was all he said and I slowly wrapped my fingers around it, stroking it slowly like I would my own, and then looked up into his eyes. We both smiled and then I licked my lips and slowly parted them. I licked the shaft, then I kissed the head, once, twice and then slowly took him in. I did to him what I always wanted done to me. He loved it and so did I. I have no idea how long this went on but I just seemed to worship having him in my mouth, slowly working in more and more while stroking him and feeling his lace covered body.

He broke this off, reluctantly, and knelt before me, coaxing me out of my clothes now. I was soon laying back on the bed giving him access to removing my pants. Now I was completely naked and he climbed on top of me, kissing me and grinding our bodies together. He slowly slid down my body and took me in his mouth, showing me how much I had to learn.

There is something incredibly sexy about looking down my body and seeing my lover's eyes staring up at me. I could see him smiling at me as Jackie continued to kiss, lick and suck on my in a way that no other person ever had. What made this lover better than the others did is that he was a man like me. He knew through first hand (no pun intended) experience how to hold it, to squeeze it and to stroke it. He knew exactly how to massage my balls. He knew how to read the signs my body was giving him and I was putty in his hands. I was completely at his control and I just loved feeling that way. He wasn't dominating me, he was simply pleasuring me and doing whatever he wanted to me and I wanted him to keep going, which he did.

He stopped for a moment and slowly kissed his way up my chest, sucking on my nipples for a few moments, then my neck. His lace-covered body felt incredible pressed against me and I wrapped my arms around him to hold him tightly against me. As I did, he began to grind his body against mine slowly, whispering in my ear, asking me if I was happy to be there, telling me how happy he was that I came and how pleased he was with me. Here he was, dressed like a beautiful sexy tv, complete with a beautiful pair of breasts oozing out of a beautiful bra, yet it was I who at that very moment was feeling like a girl on her first date, being seduced by my man who knew exactly what to tell me to get me to kiss him, tease him, touch him, feel him and taste him. My heart felt like it was beating out of my chest, I could barely speak, and I was so very happy to have taken this chance. I whispered back telling him that I was really happy to be here and that he was everything that I had hoped and more. He loved my reply and kissed me hard. I automatically parted my lips and awaited his tongue to touch mine. It was electric. We kissed for quite a long time, and as we did, my hands played with his hair, held his shoulders, slid down his back and played with his smooth sexy ass. He had slid his hand between us, slid off to the side just enough and began working his magic on my cock once again.

After several minutes of intensely erotic kissing, we broke free, took a breath and shared some more wine. As we stood there sharing the wine, my eyes scanned his body from top to bottom over and over again marveling at what I was seeing. I moved behind Jackie and held her close as we stood in front of the mirror, illuminated only by candlelight. Jackie let out a sexy little moan, began to press back against me, and tilted his head back. I took the opportunity and began to kiss his neck and then his lips. I put my wine glass down and without breaking the kiss, took his too. Now, with my hands free, I began to explore his body once again. I began by reaching up and taking his beautiful breasts in my hands and squeezing them. He just loved that and moaned again showing his approval. Watching in the mirror out of one eye was even more exciting. I watched as I lowered one hand down lower, lower until my fingers danced across the garter belt, following the straps down to the stockings, and then back up between his legs until I reached his panties. I slowly traced the outline of his cock, following it from base to tip and back again, teasing him like I wanted to be teased. Then I placed my palm flat against him and felt the radiating warmth. "Yes," was what he whispered and I knew what that meant. This was almost instinctual for me too. Even though his was the first cock I had ever held or sucked, I knew what I would have meant by saying "yes." I slipped my finger into the panties and slowly peeled them back far enough for me to slide my hand down into them where. I was tingling all over as I wrapped my fingers around his cock again and watched myself in the mirror giving him a slow deliberate hand job, first with one hand and then my other hand joined in too.

We stopped after a what seemed like forever, and he told me that I needed to sit down on the bed, have another glass of wine and wait while he went and changed. When Jackie came back he was now dressed in a whole different outfit, and it was incredible. He had on all black. He knew I loved stockings garter and panties, and he didn't disappoint me. He also had on a beautiful body tight lace camisole that showed off his bra beneath. He sauntered up in front of me, placed one foot on the bed next to me and asked me if I was happy. I reached up and ran my hands up his stockings, across his garter and back down again. As I did, he shifted ever closer and I leaned forward just enough to plant a soft kiss right on his lace covered cock. This time it was me looking up into his eyes and I could tell that turned him on too. He told me to lay down. Then he said that it wasn't fair that he was the only one wearing lace and that something "had to be done about this." He held out a pair of stockings and dangled them in front of my face, dragging them across my chest down to my cock. Jackie had a big smile. I watched as he rolled one of them in his hands. I knew what he wanted, and I wanted it even more, so I lifted up one of my legs and watched as he slowly slid the stocking up, first one, then the other. He ran his fingers over my now stocking covered legs and smiled at me. He told me to stand up and then we switched places, he on the bed, and me in front of him. I was incredibly nervous and turned on at the same time. I was standing in front of him and my cock was rock hard. He placed a garter belt around my waist and fastened them to the stockings. I loved turning around and feeling him do this to me. Then he held out a beautiful pair of matching panties for me too. He helped me into them and even was "kind" enough to tuck me in properly. He held out a bra for me and I nearly giggled, telling him that I was just a little "flat" for the bra. I should have known what he had in mind, as he then reached over and picked up a couple of breast forms. He helped me into my bra, situated the forms inside and then had me stand in front of the mirror with him. I watched as Jackie explored my lace covered body in the mirror and was loving it.

We shared some more wine and kissed in the mirror again. There was something incredible about seeing myself dressed like this and being seduced by Jackie at the same time. He whispered in my ear telling me how sexy I looked, and I thanked him. He had one hand on my hip and one on my stomach. I had a glass of wine in one hand and my other one was placed on top of his. As I started to take a sip of wine, he began to move our hands down across my stomach. I took a mouth full of wine at the same time as our hands reached my panty covered cock. I turned slightly to the side so as to kiss him, and as he continued massaging me we shared the same sip of wine. We went back over to the bed and sat down together. I laid down and pulled him next to me. Jackie placed a leg over mine and rubbed them together. The sensation of having two stocking covered legs rubbing together was electric. He reached over and slid his hand right inside of my panties, wrapped his fingers around my cock and continued to seduce me. He changed his position in bed and began to take me in his mouth again, slowly, kissing it, licking it and just teasing me more. I wanted, no needed to return the favor so I reached out and coaxed him closer to me so I could begin to feel him again. I massaged his cock through the panties until it was nice and hard. I just loved watching it get hard again and knowing it was me who was doing that to him. I then peeled back his panties, wrapped my hand around his shaft and moved closer until I was only inches away it. I actually felt my mouth begin to water in anticipation. I licked my lips and then slowly guided my mouth right to it. I parted my lips and began to work my tongue around the head and tried to take as much of it in as I could, then I began to slowly suck it and slide it in and out of my mouth, enjoying every moment. I just loved how warm it felt in my mouth and how smooth it felt to my tongue. Everything he did to me, I tried to mirror. He knew that this was my first time but he made me feel so special, telling me how wonderful I was making him feel. When he stopped to watch me, I became a little nervous. He must have sensed this because he just ran his fingers across my hair and told me how much he loved watching me. That was all the encouragement I needed to continue.

He rolled over above me as I continued to hold him in my mouth. I reached out, grabbed a pillow, placed it behind my head and never missed a beat. Jackie began to play with me again and slowly worked my panties down. As he did, he forced my cock to pop out and slap back against my stomach. He got me to lift my hips as he slid them all the way down. He reached over to the nightstand, and then came right back to my cock again, stroking it and kissing it again. He gently lifted one of my knees and the next thing I felt was his finger right against my opening. I made absolutely no attempt whatsoever to discourage his advances. His finger was cool and slippery as he began to play with me. He slowly slid his finger inside of me and began to work it in and out in the same rhythm as I was sucking him. It was such a turn on feeling him fucking my mouth and ass at the same time. He then applied a little more lubricant and added another finger inside of me. As he did, I reached down, grabbed my cock, and started playing with myself. He really enjoyed watching this too. He warned me not to cum, just to play, and I obeyed. He asked me if I wanted to feel something really wonderful (that was a silly question) and I managed to eek out a "uh huh." Jackie removed his fingers from me and began pressing something else against my opening. It was not warm like his fingers, but I did not care. In my head, I knew what it was and I wanted it. He began to work the dildo inside of me and it felt so nice. I had to stop sucking him for a few moments just to feel this. He took his other hand and placed it on mine as we both stroked my cock together. I let him continue and I reached over to find his cock again and began stroking it and scooting myself closer so I could take him in my mouth again. He complimented me on my "new found talents" and I felt myself blush. He slowly removed the dildo from my ass and when he did, I found myself pushing my hips upward to find it once again. Jackie said, "well, it seems like I know what you like, don't I? What do you want me to do? Tell me." He wasn't satisfied until he got me to say that I wanted him to fuck me. I did it! I actually said it.

He turned around and then slid off the bed for a moment, never releasing my cock and returned to the matter at hand. He took my cock into his mouth again and really drove me crazy. I told him that I wanted to cum and he just smiled. I took this to mean that he was ok with it. His tempo increased, my heart rate increased, the dildo plunged one last time deep inside of me and that was all it took - I started to cum. This orgasm did not seem to stop, nor did I want it to. When I stopped, he slowly removed the dildo from inside of me, slid up next to me and started to give me a kiss. As I took his tongue deep in my mouth, I could feel him release something warm that began to cover my tongue and his. I knew what it was and found myself totally turned on by this. I had secretly tasted my own cum before but never like this and I loved it. Jackie was really turned on by this too. I think he thought he was going to surprise me. He reached down and squeezed the last few drops from me, coated his finger with it and brought it up to my lips once again, painting my lips as if it were lipstick. He put his finger in my mouth and I licked it clean and then licked my lips. I lay back with my head on the pillow and he snuggled in next to me with one leg over and in between mine, and an arm across me.

The room was dead silent for several minutes. The only sounds I heard were my heart beating and his breath near my ear. The silence was broken when he nibbled on my ear and asked me, "So...what do think? Was this what you expected?" I pulled his leg up between my legs so I could feel the warmth of his thigh and told him that this was not at all what I had expected. I had hoped that I would like being with him. I had hoped that I would enjoy being with another man. I had always fantasized about sucking another man's cock. I told him that there were not enough words for me to describe exactly how I was feeling at this moment. He asked me to try so I did. I told him that this was by far the most exciting, most sensual, most sexually erotic experience I ever had and I could not have ever imagined just how much I would enjoy this and him. He kissed me again and told me how happy he was that I had chosen him to share this with and said that he could not believe that his was the first cock I had ever sucked. I looked him right in the eyes and with a big grin assured him that it was.

We shared another glass of wine and just laid in bed for a short while. Then Jackie asked me if I'd like to see some more of his lingerie collection. We had emailed several times before we met, and he had sent me several incredible pictures of him in different outfits and we discussed which ones I liked and why. He got up and went to the dresser, searched around for a few moments and told me he'd be right back. When he returned, he was wearing a long basic hotel robe that covered everything except for below his knees. At least there, I saw the red stockings and heels, but nothing else. He told me that before I could see what he was wearing, I would have to strip for him. I hated the idea of taking off the lingerie but what else could I do. I stood up, and teasingly unhooked the garter belt and tossed it across the chair. I then rolled down the stockings and laid them across his shoulders teasingly. I told him that I couldn't undo the bra and he told me to leave it on. He told me to close my eyes and tell me what I feel. He approached and started playing with my breasts. Then he kissed my cheek, my neck, my stomach and took me in his mouth for a brief moment again, warning me not to open my eyes. Then he stood back up and I felt him drape something silky across my shoulders. He asked me if I liked the way it felt and I said yes. He had me sit down on the bed and he took my feet in his hands. I felt him pull a stocking up each leg once again, only this time when he had me stand up, he continued to work this up my body. When he finally had me open my eyes, I could see that he had put me into a full, tight, lacy bodysuit. He kissed me telling me how nice I looked. I coyishly thanked him.

Now came his turn. He had me sit back down and watch as he peeled back the robe. He looked incredible. He was wearing an all red, Valentine's Day red, lace bustier with garterbelt, panties and the stockings. He filled out that bustier in a way that I couldn't believe. I looked over at the clock just to keep an eye on things, as I couldn't let the day get by. I still had to get back to "reality" at some point. I was so drawn to him again and told him so. Jackie smiled and walked over to me, put his hands on my shoulders and told me to show him. I knew what that meant. I reached out, put my hands on his sexy little hips, and pulled him closer to me. I began to slowly work my hands up his legs, feeling every inch of lace until I got to the straps of the garters. I traced up the straps and followed all six of them, carefully avoiding touching anything else quite yet. I continued up to his breasts and squeezed them, wishing they were real but man did they feel real. Jackie even responded as if they were which turned me on a lot. Then I leaned forward, pressed my lips against his cock, and began to massage it with my lips, feeling it grow before my very eyes. With one hand, I began to massage his cock through the panties as I kissed and eventually I peeled down the top to expose it. Now it was my turn to ask him to tell me what he wanted. "Tell me what you want Jackie!" He didn't hesitate. "Suck me like you love it!" I pulled down just the front of the panties, far enough that I could free his cock and wrapped my fingers around it, then pulled him a bit closer and scooted myself a bit closer so I could get comfortable. I reached up with my other hand and gently held his balls in my hand, then I licked my lips so he could see them, and then took him in and began stroking him, massaging him, licking him and sucking him all at once. This is what I love so I hoped he would love it too. I loved to stop sucking him just long enough to try to milk a drop of precum from the tip so I could lick it with the tip of my tongue. I think the room could have been on fire at that moment and I wouldn't have known. I was mesmerized by this thing of beauty before me and all I wanted was to please him. I could feel his balls begin to tighten in my hand and sensed that he was close. He asked me if I thought I was ready for him to cum and I let out an "uh huh." I had searched the internet long and hard, reading about blowjobs and first experiences so I had an idea as to what to do. Jackie began to squeeze my shoulders and I knew what was next. I began stroking him faster and began swirling my tongue around the head in anticipation. What happened next was incredible. He arched his back, held me by the back of the head and then I felt him begin to cum. My tongue trapped most of it so, like a good girl, I didn't choke. There really wasn't as much as I had thought there would be, or maybe even hoped there would be, but I didn't mind. I ran my tongue around the inside of my mouth, circling his cock head and coating my whole mouth with his cum and then swallowed some of it. I don't know if it was because I was so into the moment or not, but I loved every drop. I put it back into my mouth and milked every last drop I could. Jackie dropped to his knees and told me how incredible that was. He told me that he just loved watching me go down on him and couldn't believe what a fantastic cocksucker I was. There was that word. Nobody ever said that word in a nice way before, but actually, this was exactly what I was at that moment. Jackie wanted me to talk about it now, asking me to tell him what I liked, how it turned me on, how it tasted. I actually felt a little shy about this, but figured I had just given my first blowjob so how shy should I be!

He told me that the least he could do in return was give me a nice massage before we had to get all cleaned up. I rolled onto my back and stretched out on the bed as he straddled me and began to rub my shoulders. He would lean forward to "push down on my back" but I really think it was to let me feel his cock pressing against my ass. That's what I told him too! I asked him if he was trying to tell me something and he said that in fact he was. He had selected a crotch less bodysuit for a reason. He again lubed up my backside and slipped one then two fingers inside of me, forgetting all about my shoulders. He then told me to roll over as he continued to massage my prostate. He handed me a condom and asked me if he could try something special with me. "Please," was all I said. He had me put the condom on him. I felt like a girl on a first date trying to do this. It was actually kind of fun! I unrolled it and stroked it to make sure it was on good and tight. Now, I laid back and lifted my knees so he could finger me again. I loved how me made me feel and could barely breathe thinking about what was coming next. He grabbed his cock and ran the head all around my opening. This time, unlike the dildo, I could feel the heat. He slowly leaned forward millimeter by millimeter he began moving in, then out, a little deeper, then out again until I could feel the whole head sink inside of me. He knew just what to do and he stopped, right there and just relaxed for a moment letting me get used to this new sensation. He began again slowly and soon I could feel his body touching mine and knew he was deep inside of me. He leaned over and whispered that he loved my ass, and I responded by telling him that my ass loved him too. He fucked me slowly for quite a while. He had me roll over on my back again and took me from behind. It felt wonderful but I liked watching better so we switched again. Eventually he just started to go soft. We giggled about it and I didn't mind. He slid over and grabbed the dildo again, holding it in his mouth like Casanova would have done with a rose, and then slid it back inside of me. He took me in his mouth again and began to give me another one of his fabulous blowjobs. I just ran my hands all over his and my body, feeling the lingerie and loving the moment. He took his mouth off for just a moment, urged me to cum for him, and then continued without missing a stroke. I did, and this time, with the dildo still inside of me, he kissed me and shared my cum once again.

I was completely spent. My mind was spinning. My body was tingling. I had just spent the past 6 hours in a hotel room with my forbidden lover and while I wondered whether I would be able to even kiss him, I had now gone much farther than that. The best part was that I loved every single moment of this day. I loved the anticipation, the kisses, the lingerie and the wine. I loved the way it felt to have his cock in my hands. I loved holding and massaging his balls. I can't believe how much I loved having his cock in my mouth. I can't get over how incredible it felt tasting his precum and then having him cum in my mouth. And as if all of this wasn't enough, I can't stop thinking about how wonderful it felt having him deep inside of me. I shared all of this with him and we hugged and kissed again.

I told him that as much as I never wanted this day to end, I would have to get going, so I asked if I could take a shower. While showering, he turned the lights off, brought in two candles and the rest of the wine and then stepped into the shower with the two glasses. Jackie told me that he couldn't let me leave without toasting our date together. We toasted, shared a mouth filled wine kiss once again and then put the glasses out on the counter. He stood behind me and washed my back, my legs and my ass for me and then, reached around and started washing my cock. My hands immediately reached for the soap, and then behind me as we washed each other's cocks. I just leaned my head back onto him and focused on the situation at hand. I couldn't help myself. I insisted that we get out and jump back on the bed for just a quick moment more. There, for the first time I saw Jackie completely naked. I looked up into his eyes and with a evil smile I told him that he had five more minutes and it was up to him what he wanted. He grabbed my hand and placed it on his cock. I knew what he wanted and he knew that was what I wanted too. I bet myself that I could make him cum in less than five minutes, so I proceeded to put forth the best effort I could. I was right! Soon he was arching his back and telling me to get ready. I sucked, and stroked, and sucked and stroked and took every last drop of him like a pro. In fact, I was actually proud of my newfound talent.

Now, I had to get dressed and there was nothing that would change my mind. I was complete! As I looked around for my clothes, he handed me the black lingerie that I had on first and told me to wear it home under my clothes; they were a gift from him to me. At first I protested but then thought that would be really kinky, so I agreed. He hurriedly helped me into my stockings, attached the garters and slipped on my panties. He handed me a black bustier instead of the bra and said this was just something special he wanted to see me in. I dressed, modeled for him and proceeded to put on my pants. Before I even got them above my knees, he pushed me down, grabbed my cock and told me he couldn't let me leave just yet. Before I could even say a word, he had me in his mouth again. So what was I supposed to do? Complain? No way. I came again, filling his mouth and we shared it one last time. As I dressed, I could feel the lingerie under my clothes, and taste my cum in my mouth. He slipped on a robe and walked me to the door. We kissed goodbye and he handed me a little bag. In it was the bodysuit and another set of white lingerie that matched his red one. He made me promise to email him as soon as I got home.

I got home and just sat down in amazement as to my day. I knew that this day would change me forever and I was right. I wrote him and told him how much this day meant to me and he replied that he too was beyond pleased with how it turned out. He lived in Idaho and me, I live in San Diego. I made him promise that if he was ever coming back, or if I could entice him to come back, that he would. It's been nearly a year now and I have completely lost track of Jackie. I fantasize about him all the time. I dream about meeting him again and picking up where we left off. I dream about finding another lover with whom I can experience even some of what I had with Jackie. I hope that one day I will. In the mean time, I wear the lingerie from time to time, sometimes even under my clothes when I go out, and will always remember that day.

 

All of this is true. I'm sure I have forgotten some of the details but a date like this will be tattooed on my mind forever. I anyone would like to talk about this with me, or share similar experiences, or maybe even meet one day, please write me and let's see what the future will bring.

I use a hotmail account too. If you want to reach me, simply write to diamond_socal and you'll get a reply.

I hope you enjoy reading about my encounter as much as I enjoyed experiencing it.

If you liked this story and would like to hear more, please feel free to contact me. I would love to hear from you.

  

  

  

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