My Little Teddy Bear -Chapter Two Ovdoc

Although Mike called me several times the week after we got home, he let me know he was hurt that I had played with the two boys on the camp out. He and I both had fun teasing each other about liking each other. He knew this was not the way it is supposed to be, but he was not into girls yet and liked the stuff we were doing. He didn’t really understand his body or his feelings yet. This was a forbidden friendship just between the three of us.

A couple of weeks later I was invited by a friend to join him at his cabin in the mountains. He was meeting a teen whose family also had a cabin at the retreat. He explained the teen was really hot, and they liked to play. He made it clear I was more than welcome to bring my own boy. Dick and I had gone off on trips before just to get out of town. We both liked boys, and liked comparing them while taking them out to a movie and a dinner. I had never been to his cabin, but knew it would be fun. He was surprised when I asked if I could bring two boys. I couldn’t wait to get Bobby and Mike to go so I could show them off.

I called both boys, explaining that it would be fun to fish, hike, and swim all weekend. We would have three nights and two days to get acquainted. I figured they had seen enough to be at ease if Dick and his boy got personal. Both boys were excited, and asked their parents. Bobby had no problem, but Mike’s family had other plans. I could hear the disappointment in his voice. Knowing his temper, I knew he had put up an argument, but his dad was just as stubborn as he was. I wondered if Mike’s brother Gary had heard them argue, and if he suspected that his little brother had found out what sex was.

Although I was worried, nothing happened except that Mike called to say he was grounded for arguing with his dad. He was still upset that he couldn’t go with us.

When the day came to leave, I picked up Bobby right after school. We headed for the mountains. That meant spending several hours on the road. Bobby knew I wanted to play. He sat close to me allowing me to use my right hand massaging his upper thigh. When his beautiful smile told me he was ready to play, I moved my hand into his crotch and found a stiff little shaft pushing up against his shorts. Bobby did his part by placing a hand on my own shaft to feel and play with it. He was relaxed and seemed to be having fun being alone with me. It was like our own time together. He and Mike had started playing around with each other at home.

Once we arrived at Dick’s cabin, we found out his teen had not yet arrived. He gave us a tour, showing us our bedroom upstairs. It had one small double bed. Bobby checked it out by laying on it. He also gave me an impish look. He knew we would be sharing the bed that night. I returned his smile with an equally evil look.

After Dick served us a delicious dinner, we settled down to watching TV and playing video games. Bobby knew Dickie liked boys. Dickie was so impressed with Bobby that he could not keep his eyes off him. Not only did that impress Bobby, but he encouraged it by stripping down to his underwear. His tighty whities showed his little three inch dicklet that stayed pretty much semi stiff. Dickie reminded me that he preferred boys in their later teens, but I knew him well enough to know that he also loved to come on to younger boys. And Dickie was licking his lips dreaming about Bobby. It was all he could do to ignore Bobby’s natural tan, not to mention his perfect features.

Dickie’s boy Doug showed up after dinner. Doug was about fourteen, lanky, thin, very cute. When Dickie answered the door, Doug didn’t hesitate to jump into his arms to hug and kiss him. No wonder Dickie couldn’t wait to see him. Doug’s family had a cabin nearby, and had arrived late. He was allowed to visit Dickie, but had to return later. For that reason, he stripped to his underwear as Dickie introduced him. He looked over Bobby, and it was clear he liked what he saw.

Bobby looked at me in disbelief as Dickie and Doug striped down to make out on Dickie’s recliner. It was clear they were going to skip foreplay and get to the fun part. He followed Doug’s lead and striped to his underwear. And instead of sitting beside me, he climbed onto my lap, wrapping his arms around my neck and laying his head on my chest as he watched Doug.

A short time later, Dickie and Doug stood up to get rid of the underwear. Dickie suggested they move to the bedroom, but Doug wasn’t shy. He laid on his stomach on the den carpet in front of the TV, spreading his legs wide as Dickie greased up and knelt on his knees slowly lining up until his dick found the mark, easing slowly inside. Doug watched TV glancing back only briefly as Dickie settled on top of his back. He did look up at Bobby wondering perhaps if Bobby had ever done this for me. (Bobby had not gone this far, and watched curiously as Doug seemed satisfied and relaxed.)

Again Bobby followed Doug’s lead, standing to allow both of us to slide out of our underwear. He had taken note of Doug’s cut five inch stiff, bushy light brown pubes, and hanging ball sac. Bobby seemed to be remarkably more at ease with the sex thing here, and laid on the carpet next to Doug, watching intently as Dickie slowly started his rhythm rocking back and forth moving his his six inch thick shaft around inside Doug, who quietly moaned in pleasure. Bobby curiously rotated his gaze between Dickie and Doug. Both were smiling back at him. Both seemed to be enjoying what they were doing. I doubt Bobby even realized I had picked up a tube of K-Y lube, and was spreading it over the length of my seven inch shaft. He didn’t even look back at me. He knew I had screwed the two boys in the tent while he and Mike had watched. He knew I had brought him on the trip to have sex. And Doug made it look easy. Maybe even fun. I’m sure he still felt nervous about getting a big dick stuffed up his poop hole, but now was the time to try it. He knew I wouldn’t intentionally hurt him. Still, he was not going to be the one to ask.

It was my move. Bobby would never be more willing than now. He had even spread his legs knowing I would want to open them. He only glanced up briefly as I knelt behind him lining up to connect. He smiled nervously looking at Doug as I slid my dick up and down his crack and greased it. Then I slid my finger inside to stretch him. At first, he resisted, but didn’t say anything. Finally, he relaxed and allowed the finger to slip inside. As soon as he allowed it, I slid the second one in. He was tight, and I sure loved the cute little bubble butt buns.

 When he pushed his butt up to meet the fingers probing for his fun spot, I knew it was time. I pulled the fingers out, replacing them with the real thing. Bobby wasn’t going to tell me when to screw him. He would leave the time up to me. That was fine. I had to try several times to open up his tiny hole, but I was more than willing to try again. The third time, I held it tightly in place until Bobby decided to open up. He relaxed, allowing the big mushroom head to pop inside. He moaned, grabbed a pillow, and gasped as the log slid in. Doug knew now it was his first time. He paused with Dickie long enough to hug Bobby and tell him to push back as I pushed down. Bobby listened and complied. With his help, I slid in quickly.

Once I was in, I paused. Bobby let Doug and Dickie know I was in. He announced it proudly. Both of them congratulated him for handling it so well.

Dickie went back to the job at hand, and vigorously pounded Doug’s well used butt. Doug rocked and rolled with every thrust. It wasn’t long before Dickie’s wild grunts indicated he was very close. Doug rose to the occasion. He knew it was time. Dickie soon blew his load, loudly announcing it. Doug lay quietly when Dickie dropped exhausted on top of him. They both exchanged hugs and kisses as Dickie waited to get his breath back. Dickie had gotten what he wanted. Doug was pleased that he had made Dickie happy.

I had just got my rhythm going. I slowly rocked back and forth pulling back to thrust in deeply. Bobby was feeling new bolts of pleasure he never knew existed. He was soon moving in rhythm with me. Bobby had decided sex was fun. I even pulled out and turned him on his back to watch his beautiful face as he watched the big round toy ease back in. While we hugged, kissed, and caressed, I trained him to please me. Bobby loved it. Putting aside his macho act, he gave in to a new form of pleasure he would learn to like. As I increased my pleasure, he gave back as much as I gave him. He knew when my dick started throbbing deep inside him. He could feel it jerking as the sperm exploded into his boy hole. Both of us rolled over and hugged as I came back to earth.

Once Dickie and I had pulled out and retreated to our place watching TV and relaxing, satisfied that we had made love to our boy, Bobby remained laying flat on his stomach. Doug had mounted him, and was sliding in to play, and to show Bobby how to have more fun while being a bottom. Bobby was just pleased to have his new friend teach him how to “do it”. When Doug was ready, he showed Bobby how to orgasm several times before wearing out exhausted.

Doug got back into his clothes. He had to return home.

Dickie was ready to turn in for the night. Bobby and I showered and climbed into our double bed. After several hours of rest, I woke, rolled Bobby over, and once more enjoyed his treasures. He was so tired, he was in and out of it, even to the point that he only grunted a little as I shot my second less vigorous load inside him. He was more aware of me as we repeated the fun late that morning. We slept in until Dickie loudly warned us he was having brunch without us.

Doug was back that afternoon after doing his chores at home. We went swimming in the cold stream running next to the cabins. That gave us an excuse to stay in our swim suits while running around the house. Dickie entertained company at times during the afternoon, including Doug’s family. For the next two days, Doug encouraged Bobby to have sex with him. I didn’t mind because Bobby also got used to playing sex games with me as well. He was obviously tickled that he was the object of affection all weekend. Being spoiled was fun. He was competing with Doug for our attention, but knew that Doug loved making love to him. (And he liked it too.)

When Sunday rolled around, we knew we had to go back home. Bobby was both happy and sad about that. He wanted to get back home, but he could not even tell them why he had had so much fun. And he never got so much attention at home. No one would be trying to lure him into the bedroom for sex. No one would even know he knew ten times more about sex than he did before. Not to mention that he was sleeping with a man. Dad would not want to hear that. But he could tell Mike about the weekend. (And boy, did he ever?) Goodbye hugs were exchanged as we headed for my car and down the dirt road leading to the road home.

Bobby, Mike, and I would meet often during the next few weeks. And Mike’s attitude had changed. I don’t know if it was because he was no longer as shy as when we met, or more likely it was because Bobby had demonstrated what he learned from me and Doug at the mountain cabin. At any rate, Mike and I became much more attached. He called me often. Sometimes, it was just to find out what I was doing, or if I could stop by to talk. At scout meetings, Mike was constantly by my side. It didn’t matter to him that some of the other boys were teasing me about him. And I was flattered that he was so infatuated, but he was also not yet even able to shoot.

At a troop camp out, I slipped into a tent with Mike and Bobby. After the other boys had turned in for the night, we settled down for some private fun. All of us had stripped down with me between them. Mike slid down and quickly went down on me. He engulfed about half of my shaft and began working it with his tongue while he also pumped it. It was obvious to me that he had been practicing on some one. I looked at Bobby. He just smiled and gave me his to suck on, keeping me busy. Mike did pull out in time to finish me off by hand. That didn’t surprise me. He loved watching me shoot off. Then he cleaned it up with his briefs. Bobby had already orgasmed, and watched Mike.

After resting and smooching with both of them for a while, I was ready to say goodnight. Mike wasn’t. Massaging my chest and playing with my shaft, he asked for the K-Y lube. Not believing what I was hearing, I complied, and handed it to him. Mike lubed me up good, then rubbed it in and around his hole. Once he was satisfied he had done a good job, he lined his body up with mine and lay on his side with his back to me. Bobby lay facing Mike face to face. He announced that Mike was ready. There was no need to ask if Mike was sure he wanted to do this. I knew I wanted him. Mike was a chubby little body that reminded me of a lovable little teddy bear. My little teddy bear. He grabbed a pillow and held onto it waiting for me to do my thing. As I moved into place, he moved his butt closer until my dick head was touching the tiny little entrance to his inner life. I reached around him clutching his body close. His whole body shuddered as I pushed forward and told him to push back at me. I know he was trying hard to relax. I reached down and grabbed his three inch hard pecker and his little ball sac. As I pushed in again, I massaged his goodies, playing with them to take his mind off the shock that I knew was to come.

It took a few tries before I finally felt the head ease in. Mike let out a low cry, but held still. He knew I was now in. And he knew it hurt. After letting him get used to the new feel down there, I slid in further a little at a time. It must have taken a good fifteen minutes to feel my pubes against his buns. Holding it there, I asked if he was all right. He asked me to let it rest there a minute. Then he added that it felt huge, but he knew he had all of it inside him, and couldn’t believe he had done it. He didn’t want me to take it out. In fact, he teased that I had just taken his cherry. He was pleased that he had me inside him. He wanted to please me, and he knew I wanted him. I hugged him and told him he was right. I had just claimed my little teddy bear as mine.

Bobby explained that he and Mike had practiced using things to get ready for this. Mike had wanted to do it. He was not happy that I had screwed those two other boys instead of us on the last camp out. Mike added that he would not let me forget that that wasn’t right. I knew now was not the time to admit that I had screwed lots of others. Mike didn’t want hear that. I winked at Bobby, knowing that Mike had to know Bobby had given his all to me at the cabin. (I would later find out that Mike was very angry that he was not there and felt like Bobby had cheated on him.)

I must have spent a couple of hours humping Mike that night. It felt really strange that Mike not only got used to it, but had decided he was going to like it because we were joined as one. Mike had really fell head over heels for me, not because of the sex, but because he loved being with me. This would become both a mutual love and a curse between us. For now, I was just amazed that a twelve year old boy was telling me he loved being with me. Don’t forget that I had already had an affair with this boy’s older brother. How was I going to explain that to Mike? This was definitely not the time to mention it.

The next weekend that comes to mind I was totally not prepared for. Dickie had called to tell me he was really impressed with me and Bobby. He wanted us to be his guests at his beach home. It was a beach cabin on the coast. Although it was located at a summer resort area, it was alone on a point. We would be all right at night, but there were a lot of kids there in the neighboring homes. We needed to watch out that they were not on the beach near his home. He had not met Mike yet. He had invited Doug, but was not sure Doug could come.

When we got there, Dickie confided that Doug would not show. He would have to make do with a boy he knew that lived at the resort.

We settled down at the cabin and toured the area. After a swim and a great dinner, we st around watching TV in the usual, a tee shirt and swim suit. Since I had Bobby and Mike with me, it didn’t bother me that Bobby once again tesaed and play wrestled with Dickie. Nor was I surprised when Bobby asked if he could sleep with Dickie that night. Mike liked the idea too.

As the hour grew late, Bobby and Dickie headed for the shower, and then bed. Mike and I followed their lead. After the usual shower play, we headed to the guest room.

Mike and I spent much of the night making out. We liked to wrestle, usually winding up in a sixty nine position, blowing each other. I had no trouble handling Mike’s small dicklet. He was getting pretty good at handling me. He had learned to push the shaft into his throat breathing through his nose. He had also learned to massage the shaft by using his throat muscles to work it as I humped him. He was so good at it that I didn’t last long. In minutes, I would be pumping my seed into his mouth and throat. Mike didn’t waste a drop. I would keep working his shorter version until he dry humped me. Mike couldn’t wait to start shooting. I had him convinced that the more he practiced, the sooner he would be shooting off.

Once we had finished blowing each other, Mike would grease me up. I would stretch his hole to make it easier on him. I would lay him on his back. He would watch as I entered him. We practiced foreplay once I was in. Mike loved playing with his dick while I moved my own around inside him. Whenever I brushed his prostate, he would jerk and moan in pleasure as electric pulses caused his body to arch and thrust. I loved what that did to my shaft. Then I would lean forward to suck on Mike’s ear lobes. That drove him crazy. He would once again work his hips driving me bananas until I could not hold my load back any longer. I wound up thrusting wildly inside him as I shot my load. Then we would remain locked together just loving our time as one. I loved Mike in bed. I loved mike just being friends. We would sleep on our side, with me holding him close to me.

When the weekend was over, Mike, Bobby and I spent a lot of nights with Dickie. Sometimes Dickie would have older teens spend the night. Mostly, I would join him with Mike and Bobby for the evening, but had to take the boys home on school nights. On some weekends, Doug would stay the night with us. Doug loved fooling around with Bobby. Mike clearly preferred staying by my side. I liked that, but I felt guilty too. Mike knew I was seeing other boys. He never mentioned it, and I never discussed it.