My First Times…

Introduction:
I had been talking to Gary for well over two years. Our relationship had begun online. He saw a response I had made in a chat room and messaged me. He didn’t seem interesting at first, but the more we chat the more I liked him. I’m cautious by nature so he didn’t get my real name for over six months, and even then only my first name. At nine months I gave him my cell phone number and we started talking on the phone. Ten months found us having phone sex on a regular basis, which occurred mainly on the weekends when I went home from school. The rest of the week I stayed on campus and had little privacy.
Right from the start Gary had told me about some of the things he was interested in. I’ll never forget it. The kinkiest things he told me he was into were gangbangs and bestiality. I didn’t immediately freak out, but I have to tell you that for a long time all I could think about was how sick Gary had to be to even think of something like that. Every time we had a small argument I would bring that up and how much it disgusted me and how sick I thought he was. I knew it hurt him every time I said that. When we were having phone sex I couldn’t help but think he was picturing me a dog fucking me or a bunch of guys using me. It was difficult to get through those thoughts sometimes.
I was 19-years-old when I started talking to Gary. I soon found out he was 33-years-old, white, divorced, a single parent, had a criminal history and had been in relationships with some interesting women in the past. Now, I’m black – dark brown actually – 5’3, 125lbs and have a very nice shape – 38-30-34. Up to this point I had never even imagined myself being with a white guy, let alone and older white guy who had two children and a criminal record. But as we talked on the phone his personality had won me over. It was obvious he was not the person he was when he had acquired his criminal record. His love for his children made me very aware of his affectionate side. He had sole custody of his second child and I could see why the courts had awarded him that responsibility.
Gary was consistent with me over time. He was there when I needed him to be, all hours of the day, whether it was during the day while he was at work or late at night and causing him to lose sleep before work the next day. He helped me with my homework, advised me about my diet and health, and comforted me when I was worried or depressed. Gary gave me what I need as a woman – respect, time and understanding. But it took a lot for me to learn to trust him enough to let him see me.
As a young black woman I had been raised to fear white men – especially older white men. The news was fraught with stories of white men meeting girls they met online and then sexually assaulting them, even killing them in some instances. I was taught that a white man who wanted to be with a black woman was only perverted and that our relationship would never work because there would always be the mentality of the white slave master raping the black female slave looming between us. When my family found out about him they put a lot of pressure on me to stop talking to him. But I have my own mind – always have – and had made good enough decisions in my life to remain drug-free, abuse free, and child-free. In fact, I was still a virgin.
That’s right. I was still a virgin when Gary and I finally met. We knew what each other looked like from photos taken on our camera phones. I had even seen his penis once, just before we had phone sex. I felt so skittish asking him to do that. He said he was at least 7-inches and I wanted to see what it looked like. I even had him put a measuring tape next to it so I knew it was his and how long it really was. It measured 7-and-a-half-inches in the picture he sent. I later found out that he wasn’t even entirely hard and that at full length he was a little over 9-inches and was almost as wide around as my wrist. When we had phone sex I could imagine his cock being inside me. From talking with my cousin I found out that his cock was actually pretty big for a white guy.
We lived in different states, and even though we had been talking for over a year it still took a while before I trusted Gary. It wasn’t until the fifth time we met that I actually let him touch me. We held hands of course, but I mean the kind of touching that makes your blood boil and your body cry out. He had leaned in to kiss me and I turned my head. Undeterred, he leaned in and kissed me on the neck. I had never been kissed there before, and my body melted under his lips. I closed my eyes and unconsciously moaned, leaning back to let him do more, but he pulled back and waited for me to turn around to look at him. Then he leaned in and kissed me on my lips before I could open my eyes fully. It took me a minute of breathing hard and sucking on his lips before I realized his hand was on my breast. My nipples were hard under his touch and all my senses seemed to heighten as my body went into overdrive. And then he stopped.
Gary stepped back and looked at me and I stared back at him. I couldn’t believe how wet I was and how fast I had succumbed to him. But he didn’t take advantage of me. He took me by the hand and we walked for a bit without saying anything to each other. It took me a few minutes to regain my composure. Gary could have had me right then and there if he had wanted. Didn’t he want me? Did I do something wrong? Everything had felt so right. What made him stop? Did I unconsciously say or do something that offended him? All these things were racing through my mind when he finally stopped and turned to me. He said, “I want you so much right now. This went a little fast just now and I want to take my time with you. You’re everything I could want in a woman. Don’t forget that.” I smiled and felt my body relax. I was nervous and worried for no reason.
The next time we met I was determined to have Gary. I now knew what it felt like to be touched by him, to be wanted so thoroughly. And I wanted him too. My whole body was screaming out to have him. And when we met the next time I made sure he knew it. I arranged everything – dinner, the movie, the room at the Embassy Suites. It was going to be my night and it was going to be my way. He only knew of my plans for the dinner and movie, so when I told him we had one more place to go he was a little surprised. Gary followed my directions as he drove us to our destination. When he saw where we were going he looked like he was getting a little nervous. I put my hand on his leg and looked at him and said, “This is what I want.” From then on it was magic. Gary relaxed and we headed to the room.
I already had the key so I let us in. I led him in slowly, even though I wanted him to tear my clothes off right then and there, drag me to the bed and take me. Gary held my hand and led me through the suite to the bedroom after I closed the door behind us. Our clothes were off before I knew it. His lips were on mine and our bodies pressed together and I was overtaken with heat. I could feel his cock pressing against me between our bodies. God but it felt bigger than I thought it was. I was startled for a moment, but then gave in to Gary’s hands and lips as they caressed my body. I was hot and wet and wanted him. I pushed off him long enough to get up on the bed and invite him on top of me. He crawled onto the bed, kissing and caressing my body from my navel up as he moved toward me. As he lay on top of me I spread my legs and he moved between them. I felt the head of his cock at my entrance as he kissed my neck and fondled my breasts. My back arched involuntarily and I gasped.
The head of his cock moved inside me and I gasped for air. Then, as I inhaled deeply again, adjusting to what he had in me, he pushed up and took my virginity. I felt a sharp, sudden pain, but as he pulled back I felt my body longing for him to push back in. As if reading my mind he obliged, stuffing me full of his cock once more. Still a little pain, but his rhythm drove all thoughts of it from my head as his cock found the pleasure spots inside me. I moaned and writhed under his strength as he plunged into me again and again. I couldn’t believe how good this felt. My legs spread wider and I lifted my knees up, inviting him deeper. Without hesitation he finally pushed his whole cock in me. I grabbed the comforter with all my might and felt as if all the breath was pushed from my body. It felt like he was in my belly, just underneath my belly button inside me. Gary’s balls slapped against my ass now as he moved in and out of me, pulling almost all the way out and shoving all the way back in. His width stretched me out more than I thought possible and pushed against all the right spots inside me. I tried to push back against him, but every time I did he hit so deep inside me that I couldn’t move. Then he leaned forward on me and held himself all the way inside me. He kissed my neck, ear, cheek, lips. He began to grind on me slowly, methodically. His hand under my head pulled me up to him.
Then all I could feel was him pushing in me – in, in, in. He didn’t pull back or pull out, just slowly grinded on me. And my body reacted unexpectedly. I went limp all at once and was in utter ecstasy. Only a few seconds later my whole body began to tighten up and my breathing became rapid and shallow. I grabbed his back and my fingers dug into him. My legs wrapped around his hips, my heels encouraging him to continue. Until finally we were there together. As I came I could feel every inch of his cock inside me seem to swell and harden. His head throbbed deep inside me. My love muscles grabbed his cock and milked him as he began shooting wave after wave of cum inside me. That sent me over the edge and I screamed while an intense orgasm flooded my body, drowning me in an intensity I had never experienced. We laid there naked for a few minutes, and then he rolled off me and held me. When he let me go I got up, went to the bathroom and cleaned up, then returned to the bed and Gary’s arms.
That weekend we alternated making love and simply fucking about ten times. It was unbelievable. My friends at school had often complained that their boyfriends didn’t last long enough or they wished they could get it up again faster and keep going. I had none of those problems with Gary and felt lucky to have someone that could give me what they all could only hope for with their men. Not only did I get the frequency and longevity that was the envy of my friends, but I also knew now how great a large cock could really feel. At that moment I could not imagine being satisfied with a penis any smaller than what Gary had. It seemed to fit my body perfectly.
For the next year our sex life was great. We had phone sex during the week while I was at school, and he would fly out to meet me on the weekends. We stayed at different places all over the city to keep things interesting and new. Gary never left without thoroughly satisfying me. I was addicted to him before we ever started having sex, but with the introduction of intercourse to our relationship I was now also addicted to his sex. I like control – I’m somewhat of a control freak – and Gary knew just how to take that control from me during sex, but at the same time leave me enough to feel like I still had it.
I talked to Gary from time to time about the fantasies he had mentioned when we first started chatting. They still bothered me a bit and I needed reassurance sometimes. Why would he want to share the person he loved with other men? How could he even think about watching a dog have sex with her? He didn’t want those things with me did he? I needed him to tell me he didn’t. I was his, and I was addicted to him, but I could not imagine doing those things with him. I loved him, he loved me. Nothing we did needed to involve other parties.
I frequently discussed my feelings about my exes with Gary. I knew it upset him sometimes, but I needed that. The jealousy he could demonstrate let me know he really cared about me. It wasn’t an insane jealousy, rather one that simmered and brewed until I turned the heat off. That was perfect for me and gave me the reassurance I needed. Gary knew I was attracted to all of my exes but knew I was not going to ever be with them. I was with him and that was enough for me. All my exes lived in my hometown, clear across the country from where I was now going to school. There was an occasional call from or to them to just say hi and see how things were going, but nothing more than that was about to materialize with any of them.
Christmas break seemed to arrive so soon this year. My relationship with Gary was great and I was doing well in all of my classes. There wasn’t really much to worry about and that made time pass so quickly. As per my yearly Christmas break routine, I had gotten my ticket to go home and made arrangements to stay with family. I had kept Gary my secret from my family for a long time, but I was beginning to wonder how they would react if I brought him home with me. For the most part I was sure it wasn’t going to be good. My family already had a stigma against white people, but the fact that he was older and had children made him that much worse in their eyes. I would catch a lot of flak from everyone if they ever knew how serious I was with Gary or if I brought him around. I wanted him there with me, but my family knew I stayed with them every year and if I had Gary come he was probably going to have to stay in a hotel and keep a low profile. When I proposed the idea to him he was hesitant at first and resisted being ‘hidden’ from everyone, but he understood how important my family is to me and eventually relented.
The first few days of Christmas break were rather uneventful. Gary was staying in his hotel room and visiting the sites of the city while I was with my family. Everyone was happy to see me and I reciprocated the sentiment. I found an hour or two every day to visit Gary and promised I would see him more as everyone got more used to having me around, at which time they wouldn’t miss me as much when I went out. He was okay with that, but I could see the frustration on his face and in his body language. I felt bad for dragging him along and then not giving him the attention he deserved. I was really going to have to make it up to him.
A week into my stay all my exes had found a way to contact me and knew I was in town. I told Gary about them each time I visited, along with the rest of the day’s activities – the goings-on of my family and the Christmas break adventure thus far. Again, every time they were mentioned I could see the jealous frustration on his face. It made me feel good to see that in him and know that, each time, I could say or do just the right thing to diffuse it.
One evening, when I was visiting Gary, I brought up the fact that I had talked to Shane, one of my exes. I was in the middle of telling Gary how the conversation went when he interrupted me and told me that someone had called his room earlier that day purporting to be one of my exes and told him that he had better stay away from me. In fact, Gary was told that he should just go ahead and leave town now before he got hurt. I sat in stunned silence for a moment, trying to take in what he had said and searching my conversations over the last few days for any clues as to who would have done such a thing. Gary knew the impact what he said had on me. He did it intentionally. As I looked at him I could see the frustration on his face of having to ‘hide’ from everyone and then being threatened by someone who didn’t even know him. While I was struggling for words to soothe and reassure him, Gary mentioned that he had gotten calls from two other guys later on that day with basically the same message – get out or get hurt. Now I was getting mad. Either Gary was lying – and I had no reason to believe he was – or someone had found out where he was staying, gave out his information to some people who either were or were not my exes, and now several of those people, who I probably knew, were threatening him.
For the next couple hours, neither of us really had anything to say to each other. I lay on the bed with Gary and he held me. My mind was racing, trying to solve this seeming riddle that was becoming more and more of an embarrassment. How could I know people that would do this? Our friends reflect the kind of person we are, and right now my past choices in friends weren’t making me look too good. Gary wouldn’t directly say he was mad at me, but I could tell from the way he held his tongue that he wanted to say some things he knew we would probably have to be talking about later if he said them. This was all my fault, and I knew it. And I felt even worse to leave Gary later to go back to my family who I knew wouldn’t accept him.
The next day, as I knocked on Gary’s suite door, I could hear laughing from inside and wondered who he had invited over. He didn’t know anyone here that I knew of, but they sounded quite friendly in there. I was feeling a little better about how things were going when I put the key in the door, opened it and found my exes all in there with Gary laughing it up like they were the best of friends. The quizzical expression on my face must have been obvious because Gary quickly got up and came over to greet and kiss me, holding me tight. He took my hand, led me over to the sofa where he had been sitting and guided me next to him. He explained that the next time each had called he had invited them over to discuss the situation and now they were all getting along just fine. They had been sitting around talking, and drinking from the looks of the few bottles scattered around the suite. Shane, Derek and James were all looking as good as ever. And Gary, although the only white person in the room, didn’t seem as misfit around us all as I had thought he would. That was encouraging considering the events of the last several days.
After a few minutes, Gary took my hand and got up, leading me to the suite’s bedroom. The guys didn’t even seem to notice as we left them to their musings. Once the door was closed behind us, Gary began to kiss me and touch me, and I melted almost instantly. The tension of the last couple days had made me very aware of how much I missed him and needed to feel him. Before I knew it my clothes were on the floor and I was laying on the edge of the bed, my legs hanging off, while Gary moved between them and began stuffing me with his wonderful cock. He lifted my legs up and moved in me until I was taking his whole length with each thrust. I moaned and wriggled, oblivious to everyone and everything. I needed this as much as Gary and I was only too happy to give it to him.
I was building closer and closer to orgasm when Gary pulled out of me and let go of my legs. I lay there, breathing hard with my eyes closed and my face turned on the bed, waiting for him to resume some sort of ministrations on my body. Instead, his hands lifted my legs again and his cock was once more inside me. I gasped at once as it thrust deep inside me, and where I expected it to reach its depth I felt it push further instead, then further still. I was startled briefly and opened my eyes to look at him when my eyes met Derek’s. His cock was a bit longer than Gary’s and he was smiling as I took it all, obviously having trouble breathing. I reached out on either side of me and grabbed onto the bed with all my might. His hands went to my waist and I held my legs up for him as he began to pound me with his cock. And as I leaned back to relax, finally getting used to the new depth, Derek let go of my legs and disembarked. I looked up just as Shane was moving up to me and I barely had time to react as he shoved his thick cock inside me.
My mind was a blur as, just before he entered me, I had seen Shane’s cock and could barely believe that thing was going to fit. He wasn’t as long as the others, but he made up for that in girth. Shane’s cock was almost as thick around as my wrist… well, maybe my forearm actually. And when that thing penetrated me I couldn’t help but scream as it stretched me further than I thought possible. It hurt a little at first, but the pain was quickly replaced by the pleasure of being so full. Shane leaned over and grabbed my breasts as he pounded me again and again. All I could do was lay there and enjoy myself as all the strength was pushed from me with each thrust from these cocks. I couldn’t believe I was letting these guys take turns having their way with me. When Gary had mentioned something like this to me in the past all I could do was think how sick he was and how disgusting that would be. But my body was telling me a totally different story now.
James was next, and he came and lay on the bed next to me while Shane removed himself from me. His cock was about the same size as Gary’s and I was secretly glad to have a cock back inside me who’s size my body was fairly familiar with. I rolled over on top of James, straddling him, and guided him inside me. Then I leaned forward on my hands on either side of his body and began to ride him. His depth was more familiar and his hands held me the same way Gary did. It was much easier to get my breath again and just enjoy riding this wonderful cock than it was to be invaded by the others. I closed my eyes and felt the wonderful sensations sent through my body as my breasts swayed against his chest and the others explored my body with their hands, spanking my ass occasionally. And as James pulled my body down on his, entering me all the way, I felt hands on my hips and another cock was forced into my pussy from behind.
I clenched James’ shoulders and squinted my eyes shut as the cock slowly pushed its way past my entrance and made its way up inside me. When he was finally all the way in and just holding himself there, I looked back to see Gary smiling at me. I grinned slightly and that encouraged him to begin his work. James and Gary alternated thrusting in and out of me and the sensation was unbelievable! Quickly, more quickly than I was ready for, my whole body was beginning to tremble and tighten. And as the orgasm rolled through my body I heard the pants and moans, felt the dual cocks in me stiffen, then begin shooting load after load of cum deep inside me. Being held so firmly by two men while they came was an experience I will never forget – it was amazing. The feeling was heightened, I’m sure, by my own orgasm.
For almost an hour, the four men took turns with me, one or two at a time. They all came in me at least twice each and I experienced more orgasms than I ever had in that short of a timeframe. Never would I have guessed that I would enjoy it that much. I loved the feel of each cock, the thought of these men taking control of my body in such intimate ways, the heat of their cum as it filled me each time. I loved being controlled, used. I had finally let go of any illusions of control I had ever had over sexual situations with Gary and loved the feel of my men handling me.
Gary and I had sex much more frequently the entire rest of the Christmas break. That experience did something to me that made me feel like I could enjoy being submissive every now and then finally. And as Gary asserted himself more aggressively I found myself giving him what he wanted in more and more things. I stopped ‘hiding’ him and introduced him to my family and friends. Things went much better than I thought they would. I was increasingly confident and secure to let Gary make decisions about things for us from that time on. He was someone to whom I realized I could finally release all my control and be secure. We have really only grown closer since then, and I look forward to our future adventures together with love and trust.

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