Finally Found the Courage

I had just finished posting my sequel about Robbie and I was checking my email, mainly just my weekly deleting process when I noticed an email address in the mix. My heart raced as I clicked on it. The last time I received one, it was spam and I deleted it but this one had a subject heading of simply "Hello" so I knew it was not junk. It was from Robbie. It was like a lot of his emails, short, sweet, and to the point. It simply said, "Are you coming into town anytime soon?"

As luck would have it, I was in fact coming in for a couple days to take care of some things with a property that I still own. I replied to him that I would be in town Thursday night and then would be leaving early Sunday morning to head back. He emailed back that he had been thinking a lot about our "adventures" and wanted to see if I would be interested in getting together. Could this really be true? Surely he didn't read my story. He said that he had just got back into the city. He and his girlfriend moved back to Augusta and then they broke up because he did not want to stay there. He did not get into all of the details but said that after he and I got together the sex with his girlfriend was never the same. I blushed as I read that and asked him to elaborate which I knew he would not. He is not much into writing more than one line. He did mention to me that he remembered some of the things he and I talked about many months ago which got me wondering where he was going with this.

We had several emails back and forth. Neither of us had been with anyone else outside of the current relationships we were in. He asked me if I would be interested in going out for dinner one night and then going back to his place. He told me that he had some things that he wanted me to wear and I was a little bit nervous but told him I would do whatever he wanted. I knew he would not embarrass either of us in public so I was ok with anything.

The rest of the week was extremely long as I was anticipating our evening. I felt like such a little girl thinking about him. Wondering what it was that he had for me and where he was planning on going. I got into town Thursday evening and kept myself extremely busy all day taking care of the necessary things to do at the property. A little after four o'clock I was headed back to the hotel and decided to send Robbie a text. He said that he was already at his place and as soon as I got ready to head that way. I jumped in the shaved and hopped in the shower and by 4:45 was headed to his place. I called him when I arrived and he met me at the door. I have never been attracted to men before but he looked extremely handsome. I had butterflies as I entered his apartment and I think that he noticed that. I was wearing a pair of dress pants, a polo shirt, and loafers. He was wearing a white terry cloth robe. He told me that he did not realize that I would get there as soon as I did. I smiled and admitted that I may not have obeyed ALL of the laws of driving.

I walked toward the den and he walked behind me and pulled me close to him. He wrapped his arms around me and began running his hands over my chest. His hands felt so good and I moved my arms behind me pulling him closer. I felt a bulge forming behind me and started pushing against it. He was now grinding into me and holding me tight. I felt his cock swell against the thin material of my pants as he reached down and squeezed my cock. I moaned and he immediately turned me around and kissed me on the lips. We had never before kissed and I was shocked. It all happened so fast and before I knew it, our tongues we re wrestling. It was nothing like what I expected it to be. His lips were soft, his tongue was as smooth as silk and his breath was delicious. I could not believe that I was kissing another man and enjoying it.

After a few minutes we broke the kiss and I lowered myself down his body. By this time his robe was open and I kissed my way down to his cock. It was hard as a rock and hooked to the left. I licked the pre-cum from the tip and then wrapped my lips around the head. I was again in heaven with his cock buried in my mouth, his heavy balls resting upon my chin, and a smile on his face looking down at me. I sucked him like a kid in a candy store. I bobbed up and down on his organ until he grabbed the back of my head and exploded into my mouth. He could not have lasted three minutes and had already coated my entire mouth. I swallowed every drop with his cock still in my mouth as I continued to milk him. This was also the first time that I had a chance to savor the taste of his seed. It was not as salty as I was expecting it to be. It was very thick and milky and I loved it and wanted more.

After cleaning his cock, he stood me up. I snickered at him and smiled as I told him I was not expecting him to come that fast. He admitted that he had not cum since he and I talked at the beginning of the week. He said that he was saving that one for me (and I was appreciative for that). He again leaned down and kissed me. It was amazing and intense. I am sure that he could taste his cum in my mouth and did not seem to mind at all.

He then asked me if I was ready to see what he had in store for me to wear. I was very excited as we began walking to the bedroom. This time however we did not go to the guest bedroom as normal, we went into his bedroom. Lying on the bed was an assortment of condoms, vibrators, butt plugs, anal eases, and clothing. It looked like an adult store exploded in his bedroom. He smiled at me as I took everything in and reassured me everything would be ok. He specifically said that if there was something that I did not want to do, he would understand. I told him that as long as it did not involve pain I was fine. With that he began undoing my pants and they slid to the floor. He then removed my boxers and I stepped out of both. He fondled my balls and sucked my cock for a few minutes but I could clearly tell that is not why my pants were off. He laid me down on the bed and spread my legs open giving him ample access to my tight bud. He began kissing the back of my legs and then licking around my asshole. Then, he licked over my butt hole and I thought that I was going to jump clear across the bed. No one had ever done that to me and I was totally not expecting it to happen. He grabbed a hold of my legs and told me to relax. He continued licking around my hole and before long I felt him push his tongue into me. I loved it and tried to open my legs more to help him. He began eating my asshole and tongue fucking me. He knew exactly how to make me feel good, and boy did it feel good.

Then he reached up and grabbed some of the toys that were sitting on the bed. He took one in his hand and lathered it with oils and then slid it inside me. It was not big at all so there was no pain involved whatsoever. He continued playing with my balls as he worked the small toy in and out of my hole. Before long, he replaced it with another and then another, each larger than the one before. It felt like he was opening me up with his toys and I was happy to oblige. I was getting fucked and since he was gradually building up the size, there was no feeling of being ripped open. Finally he pulled something out that was of decent size, possibly a little bigger than he was. It strained a little going in but was not painful. He fucked me with it for a few minutes before putting some straps around my waist and between my thighs. He told me that these straps would hold the plug in place without falling out. I thought it was pretty neat and was willing to do as he wished.

He stood me up and showed me in the mirror how it came around my balls and cock and then around my waist. Then he handed me a pair of boy short panties and asked me if I would put them on. I eagerly put them on and could not contain my smile. He looked at me and asked me why I was smiling so much. I simply told him that I want to be his girl. He said that he was hoping I would tell him that because we had big plans. He said that he was not going to have me dress as a girl for dinner but he wanted me to keep the plug in and wear the panties while we were out. I happily agreed and we got dressed and ready to go. I noticed he was full mast just looking at me and I really liked that.

He looked so good when he got dressed up. He wore a button up shirt with jeans and a black pair of boots. As we walked to the door, he grabbed my hand, turned me around and planted another kiss on my lips. We walked out the door hand in hand. As we waited on the elevator, he had his hand on my butt and was pushing the plug further into me. I have never been one for public displays of affection but with him, everything was different, and besides we were not yet in public I told myself. We enjoyed a delightful dinner under candlelight and walked around downtown for a little while before heading back to his place. We were hand and hand the entire time, which is not too much out of place in the city.

Upon arriving back to his place, I was ready to explode. He seemed to take the bumpiest ride back on purpose because every time we hit a bump, the butt plug seemed to impale further in me; not that I was complaining. We got upstairs and he said that our night was just about to begin. We went back into his bedroom and he took off my panties and then removed the plug from my ass and I suddenly felt as though the neighbors could see how large my hole was it felt so big. He seemed to sense how I was feeling and sat me on the bed. He pulled out some garments from the bag and showed them to me asking for my opinion. They were your traditional sex outfits such as the maids outfit, a school girl outfit, and then he pulled out a pair of boy short panties that across the back said some sort of flirty comment. He told me that he was going to make us a couple drinks and that he wanted me to take one of the outfits and put it on while he went into the kitchen.

He left and I was there to decide what to wear. I went with the school girl outfit for the obvious reasons. I wanted to be his girl and that was what I was going to be. I put it on and walked into the den and watched him make our drinks in the kitchen again wearing his white robe. I walked up to him and whispered into his ear that I wanted him to fuck me like the bad little school girl I was. He spun me around and gently slapped my butt. He then grabbed my face and turned it to him, looked in my eyes and said "That is my ass". He handed me my drink and I sipped on it. We walked over to the couch and he sat down. He casually turned the television on and I have no clue what was on. I sat my drink down on the table and buried my face in his lap. I was so horny and turned on that I wanted his cock so bad. I worked his cock like a professional. He spread his legs open so that I could crawl between them which I did. I then licked my finger and began playing with his asshole. I looked up at him and watched his eyes roll back showing me I was doing a good job. He was very tight and his muscles contracted against my finger. I slowly moved it in and out as I continued lapping at the cock in my mouth. As I fingered his tight hole, my mind began racing and I wanted to taste his ass. I leaned up and asked him to turn around on the sofa which he did. I spread his legs open and began licking his balls which dangled heavily in his loose sack. I hummed as I pulled them into my mouth and he seemed to love it. Then I began licking up towards his ass. I had never done this before, and was worried that it would be disgusting but figured if I didn't try now, I would never know. It was anything but disgusting. I rimmed him for several minutes and he began reaching for the back of my head and pushing my face further into him. His commands began to get more vocal as he told me to eat his ass. It was so much fun making him happy.

After he could no longer take it anymore, he led me by my hand to the bed. He laid me on the bed in my outfit and just looked at my body. I felt so vulnerable but comfortable at the same time. He climbed on top of me and we began kissing quite passionately. Our tongues twisted together and then he began kissing my neck which made me squirm underneath him. He looked at me and asked if he could play with my pussy. There was no need in answering him and he pushed his legs between mine to gain access. I was still a little stretched from the plug being in me earlier and my hole was still lubed yet he grabbed the bottle of lubed and massaged it onto his cock.

He then pointed his mushroom head at my entrance and I backed up toward him. He entered me with little resistance and much delight. There was absolutely no pain whatsoever as his head popped into me and he eased his shaft into me. I do not know if it was entirely because of the earlier preparation or if it was because I was completely relaxed at the time. Either way, he was sliding his cock deep into me with each thrust and the feeling was remarkable. I continued to rock back and forth to meet him and begged him to fuck me. He was perfectly content in moving at his own pace. Each time he buried his magic stick inside me, I squeezed to hold him inside me which he seemed to enjoy. As he withdrew, he completely exited me and then plunged back inside me. Every time he entered me I received an incredible and unexplainable fullness. It seemed like he made love to my hole for hours, moving at his own slow and steady pace. We changed positions several times and I felt his cock hit more places inside my tunnel that I have never before experienced. At one point, he was lying on his back and I was on top of him riding his cock while facing him. My own cock was oozing precum as it was slapping off of his belly. He then told me to turn around and face away from him while I rode his cock. He began lifting off of the bed as he thrust into me and I began paying attention his balls and ran my finger along his bud. He moaned when I did and tried to move to give me more access. In the position we were in, it was not the easiest thing to do. Eventually he pulled me back to lie on top of him, my chest facing up. He started kissing my ears and again kissed my neck. He rolled us back onto our sides and we both kissed as he continued his slow pace. As the kissing became more intense, so did his rhythm into me. I could tell he was getting close as he moved me to my back and crawled between my legs. He perched my ankles over his shoulders and began driving his hard cock deep into me and all I could do was beg him to fuck me harder.

It did not take much time before he informed me that he was about to explode and asked me where I wanted it. I answered him by wrapping my legs around his waist as tight as I could. He needed no more instruction and continued his barrage on my hole. Within seconds I felt the single most exhilarating feeling I have ever experienced in my entire life. His seed exploded inside me so hard and so hot that it startled me at first. It was amazing. Three separate times I felt his cock head expand inside me and deposit his juice deep into my body until he finally collapsed on top of me. Shortly thereafter, his cock slipped out from my body. I scooted down the bed and took him in my mouth like it was a bottle. He still had a little cum left around the tip that I slurped up and enjoyed. Upon finishing, I moved back up the bed and told him that was the greatest experience of my life and we kissed passionately. I looked over at the clock and noticed that it was almost 11:45.

He then asked if I would be interested in spending the night with him. He gave me the greatest night of my life, how could I possibly say no. He asked me if I would like another drink and we both headed for the kitchen. Walking was not easy with the beating my ass just took but I managed. While there, I felt something crawling on my leg and noticed it was his seed. He noticed it and in a chest thumping way proclaimed my ass as his.

After fixing our drinks Robbie suggested that we take a shower so that I could get cleaned up a little bit. His shower was the largest shower I had ever seen in an apartment before. It has shower heads on two walls and a bench inside the shower. We stepped in and closed the door behind us. He began lathering his hands with soap and started soaping my body. I tried doing the same to him but he took the soap from me before I could. He massaged over my chest and arms and then sat down on the bench. He lifted each of my legs and washed them separately before turning me around and washing my back. He then put his hand at the bottom of my back and pushed me forward forcing me to bend over. He easily slid two fingers inside my hole and worked them slowly as I pressed my hands against the wall of the shower. He then turned me around and took my cock into his mouth all the way to the root. With all of the stimulation I had already enjoyed, it did not take long at all for me to explode into his mouth. Upon completion, it was my turn to wash him and I took full advantage of my time. While the actual washing may have been quick, I took extra time with his cock, balls, and ass. I wanted to make sure that not only did I enjoy it but he did as well. I have seen many movies with guys rimming other guys and while it always turned me on, I did not know if it was something that I would want to do. And while I did it in the bed with him, it was more of an impulse decision. This time was going to be different.

I took time making sure his ass was clean and then turned my attention to his cock. It was hard yet not erect. It was dangling between his legs and looked extremely appetizing to my eyes. I gently pulled back his foreskin and cleaned his cock with my hands and then gently massaged his balls as the water fell over him and rinsed as I went along. I gently stroked his cock with one hand and fondled his sack with the other. Then I kissed his cock head with my lips. I kissed all along his shaft and then his balls. I enjoyed worshiping his cock and making it grow with my touch. I believe that Robbie enjoyed me worshiping his meat just as much. He put his foot up on the bench next to me and began fucking my mouth. I really liked when he took control like that by forcing his cock down my throat. I took the opportunity to slide a finger into his ass while he worked my mouth. He pumped harder as I worked his hole. He then looked down at me and asked if I wanted to lick his hole. He turned and put his ass in my face. He put his hands on the half wall of the stall and pushed himself back to me so that I was pressed against the wall behind me. My face was now buried between his cheeks and my tongue was dancing inside his delicious hole. Robbie became very vocal and almost forceful as he yelled for me to eat his ass and tongue his hole. I was delighted to oblige. Every now and again he would reach down and play with the tip of my cock while I concentrated on eating his hole and fucking him with my tongue.

After our skin turned wrinkled, we turned the shower off and went back into the bedroom. We dried each other off and got ready for bed. He turned off the lights and turned on the television. We climbed into the bed with him snuggled in behind me. His cock was rested between my cheeks and his arm was draped across my torso. It did not take long for me to fall asleep with everything that happened that day. I woke up sometime in the middle of the night to use the restroom. Neither of us moved up until that point and his cock was still at my crack. I made my way back to the bed and cuddled up to him again. He wrapped his arm around me again and we went back to sleep.

I woke several hours later and Robbie was lying on the pillows watching Sports Center with his arms behind his head. I rolled over and laid my head on his chest. I could see the outline in the sheets of his member stirring. I reached down and wrapped my hand around him and began lightly stroking. He told me that he had to leave in a couple hours because he had a lesson to give at the club which was not a problem because I needed to get going as well. As much as I wanted to lie in bed with him all day, I knew that it was not a possibility. We got out of bed and went into the kitchen to fix some breakfast. After cleaning it up, he mentioned to me that it would be better if I were cleaning it in my outfit. With that, I went back into the bathroom and put on the maid's outfit. While in there, I took the liberty of applying a little lube to my backside with my fingers. I quickly washed my hands and went back to the kitchen. He was still sitting at the table and I picked up the plates and carried it to the sink. I began washing all of the dishes when he decided to join me. He walked up behind me and whispered in my ear, "I want to fuck your pussy again baby". My head fell backwards onto his shoulder and he kissed my neck. His hand cupped my lace panty covered ass and I moaned. I turned to face him and we kissed passionately. His tongue ravaged my mouth and I again moaned into him. Being submissive to him completely turned me on and he used it to his advantage. He knew that I would do anything he asked me to but also had the respect not to take it too far.