Fateful First Encounter
By: Date: 2021.05.05. Categories: Sex Stories Tags: , , ,

We have all had encounters that we remember and those we want to forget, however this one has stuck in my mind, even though I have tried to put it out of my mind. I find myself remembering this eventful time and as I slip back to when it all happened, I wish that I could somehow go back and relive the experience, but then I wish again to forget it ever happen.

We have all had encounters that we remember as well as those we want to forget, and this particular one has stuck in my mind, even though I have for so long tried to erase it. However, periodically I find myself remembering this eventful time in my life and as I slip back to when it all happened, it becomes as vivid as if it had just happened. Maybe I wish it would somehow happen again or that I could somehow go back and relive the experience.

I have mixed feeling about what happened and when it creeps back into my thoughts, I end up examining what actually took place, and I end up taking myself back to that fateful time in my life, reliving it. But then I wish to forget it ever happened.

I was fifteen, somewhat of a delinquent, skipping classes, To hang out at the local game room by the high school. I was a rather shy young man and even though I had had several girl friends over the years, I was still a virgin. Yes, I had plenty of opportunities, but never did it until the time when this story takes place.

Anyway, I was spending a lot of time at the game room during the day with friends, instead of going to class, and had started to become good friends with a man that worked there, that I soon discovered was the owner of the game room. His name was John, he was probably 10 years older than I was, had dark skin and dark hair, and he was very friendly.

Everyone at the school liked hanging out up at the game room during the day and sometime, even into the night, and weekends. There were pinball machines that lined the walls, foosball machines in the middle, as well as selling records and cassettes.

At first, I really did not take notice of John too much, but I think he must have been watching me and noticing how much time I was spending at the game room and at some point he must have decided to see if he could encourage me to have a relationship with him.

At the time, I had no idea John was gay but it would soon become quite evident, but at first I thought he was just being friendly because our interactions were all very innocent. Conversations were nothing more than the casual, “Hello” as I entered the game room or me asking for change to play some of the games. However, it soon progressed to where he would give me free games on the pinball machines when I was hanging out there and there were even a couple times when the attendants working at the game room started giving me pot and pills.

My friendship with John grew and soon he was asking me to go out for breakfast and lunch with him, which at first I was reluctant to do, but eventually John convinced me it would be okay. I actually enjoy skipping classes to hang out at the game room, even though my grades were hurting, and I did liked the attention I was getting.

Going out for breakfast or lunch, became more and more frequent and our conversations were innocent, at least on the surface, but I am quite sure he was always looking for an opening, a way to feel out the situation, and at the same time, trying to build me up, create a friendship that would hopefully get me to sleep with him.

There was one particular day that stands out and when I think about what happened, it was a turning point in our friendly relationship. We were out for breakfast on day, and our simple conversation turned to a conversation about girls and sex. John asked if I had ever been with a girl and at the time, I had been with several girlfriends, however I had not gone all the way, but I wasn’t going to tell him that, so I simply told him, “Yea.”

We talked about what color hair we liked, boobs, asses, etc., and we even laughed a little, but John then asked me when was the last time I had sex. After a short pause, I inadvertently let it slip that I had actually never had sex before.

He was shocked a little and asked, “Why not,” and continued by saying, “Maybe you like guys.”

I paused but quickly told him, “No, I like girls, not guys.”

He quickly said, “Then why haven’t you done it yet?”

I told him that I just hadn’t had the chance.

The conversation paused for a little bit and then he asked, “Do you ever think guys are attractive?”

I quickly said, “No,” and John continued the questioning by asking, “So, when you’re watching a movie and there’s a guy in the movie, you never say to yourself, Hey, he’s good looking.”

I again said, “No, I never thought that.”

John chuckled and quickly tried to calm me down by agreeing that he knew I only like girls, which kind of put me at ease and our conversation returned to a more innocent level. However, it was about to take another turn as the conversation paused again. I could sense John was looking at me and as he asked if everything was ok, I looked up and nodded my head.

John quickly said that he really enjoyed my company and told me it was really nice to have someone like me to talk with. Agreeing, I nodded my head, which gave John a little time to gather his thoughts, looking for a way to steer the conversation in a direction that would not only calm my thoughts, but provide him a way to find out if he could get me to go with him to his apartment.

He subtly told me he was sorry if I was embarrassed, and as I nodded my head and told him it was ok, John smiled and said, “Good,” and proceeded by again saying that he understood that I only like girls, and as I nodded my head again, the conversation paused. John then casually mentioned that he was bisexual, and looking up at him wondering what he meant, the conversation paused again; I had never heard that term before and sense I was naive about what he was telling me, he asked if I know what that was.

I simply told him, “No, I didn’t,” and as I looked at him, he smiled, seeming relishing in the opportunity to explain what it was.

He started by saying that he was attracted to girls like I was and then continued by telling me that sometimes he found guys attractive too. I was a little confused, but John continued be explaining that he like having sex with girl but that sometimes if he found a guy attractive, and they hit it off that he also enjoyed sleeping with guys too.

I was shocked, but he continued the conversation by asking what I thought about it. I did not know what to say or what to do, so I told him that I wasn’t sure. I was confused as our conversation paused for a second and I asked myself, “Why was he telling me this,” but it would soon become very apparent. With that said, John must have known the topic made me uncomfortable, because John now tried to change the subject by saying, “I’m glad I was able to tell you that,” and hesitantly I acknowledged him. He continued by saying, “You’ve been a good friend, it really nice to hang out with you.” It was kind of nice to hear but John then said, “I gotta tell you, I’m attracted to you.”

Oh my god, what was he saying?

He then said, “I don’t want you to feel uncomfortable, but I’ve even thought about asking you to come over to my apartment, but I wasn’t sure how you’d take it.”

A sudden feeling of uneasiness came over me about the conversation and after another pause, I think he realized he might have gone to far and to fast. I did not know what to do; this man was my only way back to school and he just told me he was attracted to me.

He quickly told me not to worry, that he was not going to do anything unless I felt the same way, but that he wanted me to know how he felt. I was speechless and didn’t know what to say, and I think he knew the subject was making me nervous, but he finished by asking me what I thought. I simply said, “I don’t know.”

He soon realized that he might have just lost the opportunity to have sex with me and said, “Come on, let’s go,” suggesting it was time to leave.

As we left the restaurant and headed back to the game room, he pressed the issue a little more by saying, “I hope you’ll think about it,” and told me that I had been such a good friend that he would give me anything I wanted. I again didn’t know what to say, but he continued by mentioning he would get me a girl, give me money, anything I wanted. He wasn’t going to let it alone, but I again said, “I don’t know.”

I felt uncomfortable with the thought of being alone with him at his apartment, and the rest of the way back to the game room, I was quiet. When we finally pulled into the parking lot, he again asked me to please think about it and to let him know what I would like. I nodded my head and told him that I would think about it, how could I not, He had just told me he wanted me to come over to his apartment to have sex with him, and it wasn’t sit well with me, but I did think about it.

A few days later, I did venture back to the game room to hang out with friends and when he saw me, he approached me and asked if I had thought about his offer. I told him that I had thought about it but I wasn’t sure about it.

He said, “Come on, let’s go get something to eat.”

I felt pressured to go and in the car on our way to the restaurant, he asked what it was that I would really like to have. I told him nothing and he was now hard-pressed to get an answer and again asked, “Come on, there has to be something you would really like to have.”

At the restaurant, we did not really talk about much, but I felt that he wanted to continue to find out what it would take to get me in bed, because he continued to pressure me. Eventually, I told him that I would really like to have a car. He smiled and at that moment, I knew I had just given him the opening he was looking for. Pausing, he asked what kind of car I would like to have. I told him I wasn’t sure, but he needed to get an answer so he kept probing to know what kind. He asked if I liked Camaros, Firebirds, Mustangs, etc. and I told him I really wasn’t sure what I wanted, and I think I knew I couldn’t commit, but he didn’t want to lose this chance to hopefully coerce me to have sex with him.

We left the restaurant and as we were driving back to the game room, he said to let him know what kind of car I wanted and he told me he would try to get it for me, whatever kind It was. For some reason I felt okay with this conversation, because naively I thought he had just said he’d get a car for me, and all I had to do is tell him what kind of car I want and he would get it for me, no strings attached. However, I was only thinking about having a car, not thinking that I was also giving him the opportunity to have sex with me, and probably not just once, but many times.

When we pulled into the parking lot, he reminded me to let him know what kind of car I would like, and when I said I would, he immediately asked if I would be able to tell him tomorrow. I told him I would try and as when we got out of the car and went inside the game room, we went our separate ways.

He had really got me thinking about what kind of car I would like to have and as I thought about all the different kinds of cars, one that I kept coming to mind and it was a 1956 Chevy, but what would happen if I actually went through with it and told him? I was not sure, but the next day when I went over to the game room, there he was and he came up to me and asked if I had made a decision. I was unsure as to how to answer, but I said that I had made a decision. He said, “Great, let’s go for a drive and you can tell me!” He was obviously excited as we left in his car and I told him that I would really like to have a ’56 Chevy. He told me that he would start looking for one. I then told him that I wanted it to be a two door with a V8 and I would like it to be midnight blue. He said he would get right on it.

A few days later, when I was up at the game room, he came up to me and told me he had found the car and said that we should take a drive and talk about it. I was excited and in the car, he was very good and told me he had seen the car, it was very nice, all it needed was to be painted, and that I could have it in a week or so. Again, I was so excited to see it and drive it, but now he had a question for me.

He said, “Well, since I found the car, do you think you’d like to come over to my apartment now.”

I did not know what to say and in all actuality, I had to know there was a catch to this whole thing. After a short pause he said, “I’ll tell you what, you come over to my place with me tomorrow afternoon and try it, if you don’t like it, we can stop and you can still have the car, what do you say.”

I didn’t know what to say, I wanted the car, but l wasn’t sure about going with him. We returned to the game room and as we parked, he told me to come by tomorrow and let him know what I want to do. Again, I was eager to have a car but worried about what would happen at his apartment, but I think in someway I was curious but the excitement of having the car was overpowering.

The next day, I went up to the game room around noon and was nervous about what was going to happen, so I tried to avoid him, but all I could think about was that car he promised and eventually, he came up to me and casually asked, “How’s it going?”

I told everything was okay, and then he asked, “Are you ready, what do you think?”

I simple nodded my head yes and simply said, “Yea.” He immediately asked, “Are you sure?”

I told him, “Yea,” and as I looked at him, he smiled, nodded his head and he ushered us out to his car.

As we headed off, I wasn’t sure where we were going, but I was nervous because I knew where it was taking me. Along the way, I think to break the tension, he asked if I was hunger and wondered if wanted to get something to eat first.

I said, No, I’m okay,” and thought to myself, “I just want to get it over with.”

We pulled into an apartment complex not far from the school and parked out front of an apartment, he was excited and said, “Come on,” and we went inside.

Inside, I could see his apartment was modesty furnished, very tidy, and as I looked around, I watched as he went over to the window, closing the blinds in the front room. He then said, “Come on,” leading me down a short hallway, toward what I suspected was his bedroom

There was a bathroom in the hall on the right and across from that there was another bedroom on the left with the door cracked open. As we entered the back bedroom, he told me to go ahead and have a seat on the bed. I hesitantly moved toward the bed and as immediately noticed it must be a king size bed. He had closed the door and as I sat down on the end of the bed, he walked over, closing the blinds.

It slowly became a little darker in the room now, but there was still a sliver of light that was able to sneak past. As I quickly looked around, I could see the room was very spacious and there was a bathroom toward the back. John had walked over to where I was sitting, and as he sat on the edge of the bed next to me, he patting me on the thigh and told me to relax and said that everything would be all right.

I simply nodded my head in agreement and looking at him, I noticed he was smiling. He stood up and said, “Ill be right back, why don’t you go ahead and start taking off my clothes.” He now walk toward the bathroom at the back and as he went into the bathroom, closing the door, I presumed he was going in there to take his clothes off. I sat there quietly for a second but then thought that I had better get started undressing before he returns.

I quickly took of my shoes, my shirt, pants, and my socks, and piled them at the end of the bed. I decided to keep my underwear on for some reason. Maybe it was because I was nervous or maybe it was an attempt to save some sense of dignity, but it wasn’t long before I heard the door to the bathroom open.

I turned to see him opening the door and as he came out he was wearing only a long sleeved, button down shirt. He then turned off the bathroom light and as he walked toward me, I tried to get a glimpse of his cock, but his shirt conveniently covering him and my eyes hadn’t adjusted to the dark after he turned off the bathroom light.

As he approached, I turned my gaze away from him and when he sat next to me, he again patted me on the leg, and he immediately noticed that I still had my underwear on, and asked, “What’s wrong?” obviously referring to my underwear still being on, but I immediately replied, “What?”

He quickly tried to change the subject by saying, “Never mind,” telling me not to worry, knowing I must be nervous.

I nodded my head and as I did, he stood up and told me to go ahead and lay down on the bed. As I started to crawl to the middle of the bed, he told me to move over to the edge of the bed, and he had me face the wall.

As I did what he told me, he came around the bed and knelt on the floor in front of me. He started rubbing my body, legs, and crotch, eventually spreading my legs and bending the top one, propping it up at an angle, which gave him better access.

I tried to distance my thoughts from what was going on by focusing on the window and the light that was creeping through. He was rubbing my cock through my underwear and even mouthed my cock through my underwear. He now pulled my underwear down exposing my cock. He gently rubbed it for a little bit and then he started to tug at my underwear in an attempt to take them off. Immediately I realized he was struggling and when he asked me to help him take them off, my thoughts returned to what was actually happening. I quickly sat up, took off my underwear, casting them off the end of the bed, and quickly laid back down on the bed.

He then replied, “That’s better, as he went back to fondling my cock, rubbing it and fondling my balls. I could tell he was becoming more and more horny, eventually sucking my dick, even though I wasn’t getting hard for him, because I was distancing my thoughts. He continued to try to get me hard but eventually he stopped and asked, “Does it feel ok.”

This again brought me back to what was actually happening and he asked me if it felt good and asked if I could help him get me hard. I realized he wasn’t going to stop until he had gotten me off, so I nodded my head and agreed. As he started to suck my cock again, I concentrated on him sucking my cock and thought about wanting to cum in his mouth.

It started to feel good in his mouth and I started to get hard as he sucked and stroked my cock. He kept stroking my cock, occasionally he would fondle my balls. I was really into it and as my cock grew harder, I could feel myself about to cum in his mouth, but I still wasn’t very hard yet. I tried to hold back until I was all the way hard, but This caused me to go soft again. I told myself that I had to concentrate and that I needed to cum whether I was hard or not. I was close to cumming again, and as I started to move my hips, fucking his mouth, I let it go, cumming in his mouth prematurely. I think it surprised him, because he stopped stroking when he felt my cum shooting in his mouth. My cock immediately started to go limp but he continued sucking.

Disappointedly he stopped and said,” Is that it?”

I leaned up on my elbow and looking down at him said, “What?”

He quickly replied, “It’s okay,” and asked if it felt good.

I simply replied, “Yea,” and as he got up off the floor he told me to move to the middle of the bed. I was still nervous but I quickly shifted over to the middle of the bed and laid there on my stomach. He had walked to the end of the bed and feeling him climb on the bed, John told me to go ahead and get on all fours, like a dog. He was on the bed behind me now and asked me to move up toward the head of the bed, and he inched closer, spreading my legs apart with his knees. He then reached above me, pulling a pillow out from the covers and as he put it in front of me, he told me to put my head down. As I put my head down, i could tell my ass was spread a little and I felt so vulnerable in this position, especially with him behind me.

He gently started to rub my back and my ass cheeks, eventually spreading my ass as he rubbed my ass cheeks.

“You’re really look tight,” he said, “you’re going to need to relax.”

After a pause, he jacked around a little bit and I heard something, it sounded like he had opened something and then I could hear what I thought was him rubbing his cock with whatever it was, and realized it was KY.

I was scared and when he touched my butthole, I raised up briefly and he said, “Relax, it’s just my finger.”

He told me to put my head down again and as I did, he started to rub lube on my butthole. It felt kind of good as I relaxed, but then he pushed his finger in my ass, and I again pull away slightly.

He again said, “Relax,” and told me to put my head back down as he continued to finger my ass.

John whispered, “Oh, you’re really tight,” and told me that I would have to really relax.

He eventually took his finger out and rubbing my ass cheeks again he asked if I was doing okay. I simply nodded my head and as he moved closer he asked if I was ready.

When I replied, “Yes,” he told me it might hurt a little but told me to relax. I nodded my head and soon I felt the head of his hard cock against my butthole and as he slowly started to push his cock in me. It felt ok at first, but all of a sudden the pain was excruciating and I quickly rose up and pulled away, causing his cock to slip out of me.

He immediately said, “What’s wrong?”

I told it hurt and pausing he told me, “Ok, you need to really try to relax more and that the hurting would eventually stop,” and again explained that I needed to relax. John now told me to tell him when it stopped hurting, of course so he could try again. It hurt for a little while, but I tried to delay him putting his cock in me as long as possible.

After he had asked a couple times if I was ready to try again, he finally had waited long enough and said, “Ok, let’s try again, but really try to relax more this time, especially when I am in you.”

I agreed and as soon as he put more lubricate on my ass, he proceeded to push his hard cock in my ass again. Again, it hurt and I tried to have him take it out, but he refused and when I tried to pull away, he held on to my hips, keeping his cock in me. It was painful, I couldn’t do it, I pulled away again, which pissed him off.

In a frustrated voice he said, “Come on, what’s wrong now.”

I replied that it hurt, and he said you have got to try to relax. He again told me to tell him when I was ok and at that point I realized he wasn’t going to stop trying until he got to fuck me. It still continued to hurt, aching, but he now moved closer and told me again to relax. He again slowly pushed his cock in me and the minute he was in me it started to hurt again. I rose up again, but this time he held me by my hips, not letting me pull away.

He said, “Stop!”

I reached back, trying to push him off, telling him it hurt. He told me to relax and said, “If you would just relax, the hurting will go away.”

He continued to hold me by my hips and after little bit, he started to slowly move his hard cock in and out of me, progressively pushed his cock in me a little more each time. It was still really hurting and when I asked him to stop, he just told me to relax. I tried to wiggle free but he again held me tight and telling me to stop, he kept moving his cock in and out of me.

After a short time, he asked if I was ok. It was still hurting but again I knew he wasn’t going to stop until he had cum, so I needed to let him finish. I nodded my head and as he started fucking me again, it still hurt as he fucked me. His body was now slapping against my ass as feverishly fucked my sloppy hole. It continued to hurt, but the pain was more of an ache now.

John was forceful moving me back and forth, desperately trying to cum in me. As he continued, my cock was starting to get hard, but he was obviously out of breath and had become frustrated. He then suddenly stopped, and breathing hard he tried to explain that I need to help too and that I needed to move back and forth with him.

He then said, “Like this,” as he grabbed my hips, and slowly started pushing and pulling me back and forth, and back and forth.

John then said, “That’s it, keep going.”

I did what he asked and as I tried to get into it, it started to feel good, and it obviously felt good for him too. He reached around me and played with my hard cock as he was fucking me remarking, “Yea, that’s it.” He then quit playing with my cock and as he concentrated on fucking me I could hear his cock going in and out of me, as his body slapped against me. I wanted him to cum as his strokes became quicker and more deliberate and I tried my best to match his thrusts, but it was hard to keep up. All of a sudden, he pulled me close, pushing his cock deep in me; it hurt and I tried to pull away, but he held me close, and out of breath he said, No, don’t move!”

He was obviously cumming in me, and I could feel his cock jerking slightly inside me. He was out of breath and hunching over me, he slowly started moving his cock in and out of me, but only briefly. He then pushed me flat on my stomach and asked if I was okay. When I didn’t reply, he slowly pulled his cock out of me, saying, “That really felt good,” and gently rubbing my ass cheeks he again asked if I was ok. He had now slid off the bed and when I did not say anything, he told me that I should go into the bathroom and clean myself out.

As I got off the bed, he told me to use the hall bathroom, and not looking around, I headed toward the bedroom door to go into the hall. As I left, he said to come back when I was finished.

I quickly went into the bathroom and closed the door. I wasn’t sure what he meant by cleaning myself out, but when I sat on the toilet and wiped my ass, i realized there was something there. Looking at the toilet paper I could see what I suspected was KY and probably his cum too. I panicked a little and now tried to push out whatever was inside me. I managed to push out something, and when I stood up and looked in the toilet, I could see some was floating and some had sunk to the bottom. I knew it must have been a mix of KY and his cum. I was scared, and thought to myself, “What had I allowed him to do.”

I knew he was waiting for me to return so I wiped my ass real good, and after gathering my composure, I decided I had better go back. I didn’t see him immediately but as I entered the room, he approached me and gently guided me toward the bed. As we sat down, John asked if I was okay. I nodded my head and as head acknowledged me by rubbing my thigh he quietly told me to get on the bed again.

Did he wanted to do it again, what was I going to do? I felt powerless as he pushed me to get on the bed, I didn’t want to do it again. He now told me to get on all fours again and as he climbed on the bed behind me he told me to put my head down on the pillow. He spread my legs again, and dabbed some KY on my butthole, and eventually pushed his finger in me again.

He told me to relax again, as he moved closer, but I thought, “How was he able to get hard so soon after he had cum just a few minutes ago.” I didn’t want to do it again and I told myself I would try to tighten my ass so he couldn’t put his cock in me again, but I couldn’t stop him. As he spread my ass, and pressed his hard cock against my hole, it slipped into my ass more easily than before. What was I going to do? I told myself this time I wouldn’t help. He held me by my hips and pushed against me, pushing his cock deep in me. Oh my god, he was going to fuck me again. As he started to fuck me, it felt good but I told myself I wasn’t going to help. Almost immediately he noticed I wasn’t helping and asked what was wrong? I told him that I thought we were only going to do it once.

He reached around taking hold of my cock and fondling it said, “Come on, I thought you liked it, let’s do it one more time.” When I didn’t reply, he realized he would have to force me to do it. He grabbed my hips again and started moving me back and forth, determine to cum again and it wasn’t long before it started to feel good, but I also thought to myself, “He had told me we would only do it once,” so I continued to not help.

John continued to forcibly fuck me, thrusting his cock in and out of me desperately trying to cum one more time, but it wasn’t working. He was noticeably frustrated that I wasn’t helping, because out of breath he suddenly stopped and hastily took his cock out of me and got off the bed.

I thought to myself, “What is he doing now?” but as he walked toward the bathroom, he said, “Go use the bathroom and go ahead and get dressed. He quickly went into the bathroom and when he closed the door, I hurried into the hall bathroom. I sat on the toilet briefly and tried again to push out whatever was in me, cleaned my ass, and hurried back into the bedroom to get dressed.

As I sat there on the bed getting dressed, he came out, and sat by me as I continued to get dressed. He didn’t say anything at first, but then told me how nice it was, and asked if I would like to maybe try it again sometime. I was powerless, he was my ride back to the game room and I did not know what to say. We eventually left the apartment and as we drove he suggested that he take me home. I agreed that it was a good idea, I really didn’t want to talk to anyone after what just happened.

We didn’t talk and I could feel the crack of my ass had become wet and slimy, obviously KY was oozing out as he drove me home. At the time all I could think of was wanting to get home and it wasnt long before he pulled up front of my house. I got out of the car, hurried inside, and went straight to the bathroom and tried again to push out whatever was still inside me and managed to push more KY and cum out, but not very much. I decided to take a long shower and continued to worry about what had happened. He had given me a blowjob, making me cum in his mouth and he didn’t use a condom when he fucked me.

A few days later, I returned to the game room to ask about the car he had promised me and when I asked him about it, he said let’s go for a drive and talk about it. We got in his car and as we drove around he explained that the deal was to sleep with him and to do it more than once. I was confused, but he continued by saying that I did not do my part so the deal was off.

I was in shock but after a paused he said, “Well, if you want to do it again with me, we could consider the deal back on again, but only if we do it again.” I did not know what to say. I wanted the car, but did not want to have sex with him again, it was the fact of the matter.

We went back to the game room and as I got out of the car he said, “I still do have the car and if you want to try it again, I’ll give you the car.”

I stayed away from the game room for a long time and when I did return, we were friendly, but it seemed that he was still looking for an opening to continue the relationship, and maybe in a way I was too. It was nearing summer break now and he must have thought he would never have the chance to be with me again, because he mentioned to me that he was moving closer to where I lived. I knew where the apartments were and when he told me to come by sometime, I was nervous, but curious too. I did end up visiting once, still wanting the car, or maybe it was because deep down I wanted to have sex again. When I entered his apartment, a feeling of uneasiness came over me; I couldn’t stay, I just couldn’t do it.

The car never materialized and I never again had sex with him. I did try to contact him much later, but never did find him. I have wanted to try it again, but these days, it could have deadly consequences.

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