Edward My First

In the Summer of 2001, there was no Craigslist nor were there apps you could download on your phone to help scratch that proverbial itch, just chat rooms where you hoped to find someone close by for no-strings attached sex. For me, it was Yahoo chat.

I was a 21 year old college student who had just broken up with his girlfriend and extremely bi-curious. I had, for several months, gone into straight chat rooms and pretended to be a woman. I had jerked off hundreds of times to the thought of taking a hard cock in my mouth and sucking it until it rewarded me with a load of cum. I pretended to be a woman and allowed hundreds of men to jerk off imagining me on all fours while they drove their hard, pulsating cocks deep into the pussy I didn't have. Looking back, this was all in preparation for when I finally went into a gay chat room.

At 5'10 & 140 pounds, with smooth abs and a bubble butt, I epitomized the term "twink" and I used it to my advantage. In gay chat rooms, I was immediately drawn to older, professional men and they thankfully were drawn to me. One in particular, from the very beginning caught my attention, and made me seriously question my attraction to women. His name was Edward, lived 45 minutes from my parents and was willing to meet me on my terms. He had been divorced for several years, had two teenage children, and owned his own business. We chatted for several weeks, before I finally felt comfortable giving him my phone number and when I did, we talked for hours on the phone that evening.

After several more weeks of chatting on the phone, I finally had built up the courage to blurt out "so when are you going to ask me out for a drink?" After a long awkward pause he said "just a drink, you don't want dinner or a few drinks?" We both laughed and agreed to that upcoming Friday.

Friday arrived and I couldn't wait to finally meet him. In our phone conversations he admitted to me that he liked young men with smooth bodies, so after getting home from work, I took extra care in shaving my body. I especially made sure that my ass and balls were completely smooth.

I walked into the bar we agreed to meet at, my heart was racing and for a split second I began to second my decision to meet him, but the minute I saw him sitting at the bar I immediately felt at ease. He turned around, smiled, greeted me with a hug, and whispered "you're way better looking in person." He placed a hand on my lower back and guided me to the bar, where the minute we sat down his hand went immediately to my leg, and my cock immediately began to swell. I looked in his eyes, smiled bashfully, and apologized "for running a few minutes late, took a little longer than I expected to get ready."

After a couple rounds of drink, we ordered dinner, and then began telling our life stories. Within less than hour, I knew more about him than any girl I had ever dated and I had opened up to him like I had never done before. When Edward asked for the check, I couldn't possibly even have imagined what lay in store for the rest of evening and night.

As we got up to leave, Edward looked over at me and asked if I was interested in going to his apartment and without hesitation I responded "I would love to." He lived a short distance from the bar and as we stood in the elevator he finally reached over to hold my hand. I turned to look at him, smiled, then moved closer to him. By this point, I was extremely turned on and wanted him to know it. Without hesitation, I leaned in closed and gently kissed his lips.

Once in his apartment, I was shocked by the amazing view and made my way to the balcony. As I stood admiring the view, I felt him wrap his arms around me and kiss me softly on the neck. Letting out a soft moan, I turned around and placed my arms around his neck, looking deep into his eyes I whispered "you definitely know how to make a boy feel good." He smiled, kissed my lips and said "baby, you have no idea how good I'm about to make you feel." With that our lips locked in the most passionate kiss I had ever experienced. I had fully succumbed to his charm and wanted to please him in every way.

In the midst of our kissing, we both began undressing the other, my hands unbuttoning his pants while he removed my shirt and vice versa. Within second we were both totally nude and caressing each others body. Having never been with a man, I slowly slid my hands up his chest and down his back, pinching his nipples gently. I caressed his muscular ass and pulled him close to me, our hardened cocks now fighting for real estate. The feeling of his cock against mine was surreal. It wasn't until I finally came back to my senses that I realized what it was that I pulled back from him far enough to slide my hand between us and wrap my hand around it.

Looking into his eyes, I pulled myself up on to my tiptoes, and kissed him romantically while I stroked his cock. He pulled away from my kiss, looked me up and down, then said "you sure you're up for this?" I did not hesitate when I said "yes".

Taking my hand, he led me to his bedroom and disappeared into the bathroom, where he began to run bath water. Reappearing several minutes later he again took me by the hand and led me into the bathroom where a whirlpool bath awaited the two of us. He asked me to climb in and then returned to the bedroom. He came a minute later and joined me.

Once in the bath I turned to face away from him and slid back to lean up against him. With his hands caressing my body, I turned my head so we could kiss. The feeling of his hard cock against my back while we kissed absolutely blew my mind. Reaching back I took his cock in my hand, stroked it a couple times and then began rubbing the tip with my thumb, within seconds precum was oozing from the tip.

I turned around, straddled his lap and positioned myself so that I could feel his cock against my ass. I began kissing his chest and neck when he asked "you ready to go climb in bed?" I giggled and answered, "baby, I was ready to climb in bed when I hugged you at the bar!" He laughed and said he had never been with a first-timer so eager.

We got out of the tub, dried off and walked out into the bedroom hand in hand. Laying on the bed was a matching red bra & panties set and black stockings, I turned to look at him when he quickly stated, "you don't have to wear them, if you don't want to, but I think they would look good on you." I didn't know what to think, but I put them on anyways, I wanted him to be thoroughly turned on.

Standing there before him, I felt both awkward and sexy. Awkward because I had never wore women's lingerie and sexy because Edward was standing there stroking his massive cock with a look of shear lust in his eyes.

He began to slowly walk towards me, gorgeous cock in hand, with a coy smile on his face. When he finally reached me, he took me in his arms and began kissing me passionately, his groans masking my soft moans. I had never felt this way, I had never felt so vulnerable and so willing. Picking me up in his arms, I wrapped my legs around his waist and my arms around his neck, and allowed him to carry me to his bed.

Laying me on the bed, he continued his passionate kissing and slowly began to kiss his way down my body. Sliding his hand under the bra he gently pinched my nipples as his tongue and lips glided across my chest towards my abs. Lifting my head off the pillow, I looked down at him, our eyes meeting, I reached down and stroked his cheek. Cradling his head in my left hand, I pulled the right bra cup down and guided his mouth to my right nipple. The feeling of his mouth on my nipple and beard stubble on my smooth skin had me in sheer ecstasy.

He continued kissing and licking his way down my body, stopping at the wet spot my cock had created, he looked up and said "I've always had a thing for wet panties" before running his tongue over the wet spot. Pulling my cock out, I felt his wet tongue circle the tip and then watched in amazement as my 7 1/2 inch disappeared in his mouth. Within minutes I was pushing him away and begging him to allow me to please him. I wanted him in my mouth, I need to feel his cock throb in my mouth, but he wasn't done taking me to the brink. He continued kissing and licking my body, this time focusing on my hips and legs.

Rolling me over on my stomach, he began kissing up my legs, first the left and then the right. When he got back up to my ass, he pushed my legs open, pulled my panties to the side, and buried his face between my cheeks. Pushing back against his face, I grinded my hips to provide him better access. He came up for a breath and slid all the way up the back of me, then whispered in my ear "your pussy is delicious."

He rolled off of me and pulled me over on top of him, with my legs straddling his hips, I leaned over and began kissing his lips with great passion. Grinding my hips against his, I bit my bottom lip and smiled before I began kissing & sucking on his neck. Sitting up, I turned around and leaned over to finally take his cock in my mouth. Up until this moment, giving a blow job had just been a fantasy, but now it was happening. Taking his cock in hand I gently stroked it and ran my tongue across the tip, he moaned with delight. Taking the tip in my mouth, I allowed my tongue to tease the underside of it briefly before taking more of it in. I cupped his balls in one hand while the other continued to stroke him.

Feeling Edward's hands on my ass, I realized I still was wearing my panties, so I took his cock out of my mouth and stood up. Standing over him, I began removing my panties when I caught a glimpse of myself in his mirrored headboard ... My long, slender frame looked incredibly feminine and sexy in lingerie! Slipping out of my panties, I looked down at him and noticed a mischievous smile on Edward's face, when I smiled back he asked "so did you finally see what I've been seeing?" I didn't have to answer, he already knew.

I set back down between his legs and took his cock into my mouth, looking up at him, I could tell by the look on his face that I was doing a good job. I gave extra attention to the bottom side of his cock and made sure to massage his balls. After several attempts at deep throating, I was finally successful and held him in my throat for as long as I could. I had no idea what his cum tasted like; however, his precum was delicious. Unfortunately for

him, I didn't want him to cum just yet, especially not in my mouth. I wanted his first load of cum to be deep in my ass.

Sliding up his body, I again kissed every inch of his abs & chest, stopping at each nipple to gently bite. I sucked passionately on his neck and left a soft trail of kisses up to his ear, he rolled me over onto my back and kissed me again on the lips. When he pulled back from me, I opened my eyes and smiled up at him, and told him "please be gentle." He responded by caressing my face and whispering "I will."

With that he stood up and retrieved a small bag from his closet. In the bag he an assortment of butt plugs, cock rings, dildos, and lube. "Going to use these to slowly loosen you up", Edward said as he pulled the plugs out. Sitting next to me on the bed, he arranged them smallest to largest, while my hands caressed his legs and abs. Once everything was laid out, he kissed me on the lips and asked if I would lay down on my stomach with a pillow under my hips, I quickly obliged.

Laying there, legs spread, ass in the air I glanced over my shoulder and smiled while I shook my ass playfully. Edwards slapped it gently and then began kissing it softly, with each kiss I grew more aroused. I flinched when I felt his tongue and breath on my asshole, but pushed back against his face. I reached back with my hands, moaning softly, while I spread my ass cheeks to give him better access.

Grinding my hips against his tongue, I continues to glance over my shoulders to watch him make love to me with his tongue. Gripping the bed sheets, I felt him slowly begin to slide a finger into me and shuttered when I felt his finger stroke my p-spot. Sitting up on my elbows, I rotated my body so that I could look him in the eyes. Once our eyes met, I smiled and told him "I want to be able to see you", with that I rolled over on my back and pulled up for a kiss.

I was totally mesmerized by this man and what he was doing to me. I wrapped my arms around his neck, kissed him passionately, grinded my ass on his finger, and moaned into his mouth. He slowly removed his finger then began inserting the smallest plug. Closing my eyes, I felt it inch its way slowly into my ass, then felt it bottom out. Opening my eyes, I looked at Edward and pulled him close to me, then began to kiss him romantically. Reaching down, I took his cock in my hand and pleaded for him to let me put it back in my mouth. After re-adjusting himself on the bed, I took the tip in my mouth and began to tease it with my tongue. As he continued to open my ass up, I laid there with his hard cock in my mouth, enjoying the taste of his sweet pre-cum and moaning in pleasure.

I was brought back to reality when he pulled his cock from my mouth and told he couldn't take my mouth teasing him any longer. I kissed his lips, rolled over on top of him, straddled his hips, began kissing his neck and chest, and allowed my hands to wander along his body. Reaching back I took hold of his hard cock and placed it between my ass cheeks, then began sliding my ass up and down its length. Leaning down close to his ear, I whispered "I want you inside of me", then looked him in the eyes and said "it's time".

Rolling over onto our sides, he immediately began caressing my body again and returned to kissing me ever so gently. His soft, gentle touch sent chills up & down my body. As he reached for the condom on his nightstand, I stopped him and stated "I want to fall asleep tonight with your cum inside of me." With that he rolled me on my back, placed belows under my hips, lifted my legs on his shoulder, and positioned himself to enter me. Reaching down I took his hard cock in my hand and placed it at the entrance to my ass. Smiling up at him, I took his left hand into mine, and gazed deeply into his eyes.

I had heard the first time would be painful, but nothing I had heard prepared me for the pain. As he slowly entered me, I immediately began to have second thoughts, but Edward took his time and allowed me time to adjust with each stroke. With each stroke he encouraged me to relax and told me how wonderful I felt. Within minutes he was completely inside and I could feel the tip of his cock deep inside of me. Leaning down over me, I felt the weight of his entire body on me and wrapped my legs and arms around him.

Looking me in the eyes, he asked "how do you feel," to which I replied "you make me feel sexy and your cock feels so good!" As we laid there, we began to kiss and grind our bodies together. I could feel his cock stroke my p-spot and I would moan uncontrollably.

The more I got used to his cock being inside of me, the better it felt and the more active I became. With each of his thrust, I would push my hips backs to meet his and then I would clench my ass cheeks together to his enjoyment, at one point asking "you trying to make me cum?" Pulling him down to kiss me, I replied "isn't that the point, baby?"

We continued in the missionary position for a few minutes more until he finally came in my ass, our bodies wrapped in an embrace and our lips locked in deep passionate kiss. Laying with Edward on top of me, feeling his cock soften and fall from my ass, I ran my fingers through his air and kissed his forehead.

The silence was broken when he asked "will you stay with me until the morning?" Pausing for a moment, I originally had no plans to stay, but those plans completely changed the minute he asked that question and I replied "so long as you got food for breakfast!"

As I lay there wrapped in his arms, my head on his chest, I felt a level of calm I had never felt before and felt good!

To be continued