Bro & Sis Try a New Friend

Matt and I lost our parents six years ago and hadn't seen much of each other since. His marriage to his childhood sweetheart lasted all of two years. Mine to the jock of the senior class didn't do much better. Both of us had graduated from college and had pretty decent jobs in the financial marketplace as analysts for two competing firms. Two years ago I won a week-long all expense trip for two to New York City and instantly gave him a call.

"What do you say Matt, like to spend an all expense paid week in New York City with your little sister?"

"What's this all about?" he asked.

When I told him about my winning the all expense paid trip in a local lottery he jumped at it with one proviso. "Leah, I think when you accept it you need to specify you will be wanting two connecting rooms and you will be glad to pay for the room difference from what the prize allowed for."

"Sure no sweat but you're paying the difference big shot."

"No problem skinflint," he answered jokingly.

We did most of the touristy things the first few days and then crammed a lot into the next one. That night we were too tired to go restaurant shopping so we just planned on having dinner in the hotel restaurant. We had a couple of drinks before dinner and then Matt ordered a bottle of wine from one of the tremendous wine list they presented. We managed to finish that during dinner and finally ended the night with a couple of cognacs in the lounge. Whew, I wasn't used to that much alcohol.

We had the door open between our connecting rooms so when I got ready for bed I gave a shout over to Matt's room to wish him nitey-nite but got worried when I didn't get a response. I went over to see what was wrong only to find him coming out of the bathroom naked. He had decided on a quick shower and hadn't heard me calling him. Hard as I tried, I couldn't keep my eyes above his waist and what I saw below it had me dumbstruck. His dick had to be six or seven inches soft. My mind was racing trying to figure out how large it would be in action. Damn, he's my brother, I ought to get those kinds of thoughts out of my head. Still…it is one enormous cock.

His nudity didn't phase him at all and he kept on casually walking to the end of the king size bed where he had laid out a pair of shorts earlier I guess he used for pajamas.

My tongue was paralyzed with the sight of what I was looking at and I couldn't really put two words together. He noticed my discomfort and came out with,

"If you came over to rock me to sleep I would like to use that breast for a pillow."

I almost shit with embarrassment. Embarrassment because I looked down at my nightgown and my right breast had slipped out and was staring him in the face. I ran back to my room slamming the door between ours.

He was right behind me saying,

"Leah, don't give it another thought. I was just trying to break the ice of you seeing me naked."

I wasn't only embarrassed, I was crying my heart out. How could I have been such a fool to wear this loose fitting top when I should have guessed that sometime during the week he would have seen me in it?"

He was rubbing my shoulders trying to comfort me and eventually I did calm down and muttered, "You must think I'm such a clutz."

"Nah, just my good looking sister who happens to have very lovely tits."

That set me off again and I was back in my crying mode.

"Damnit Matt, stop teasing me about it. I feel bad enough as it is."

He grabbed my shoulder and turned me over to face him. He was sitting on the side of the bed facing me and he just rubbed my shoulder softly.

"Easy does it Leah. If we can't kid each other who in the world can?"

"You're right Matt. Far be it from me to notice you came into my room with a baseball bat sticking out of your boxers."

He looked down at his crotch and said, "Oops, it wasn't supposed to do that."

His cock was hard as a steel rod and must have been at least ten inches and very thick.

Saying "Maybe I'd better get back to my own room," as he started to stand up.

"Heck, don't let me chase you away. Between my tit coming out and your cock doing the same neither of us can take the high road of decency."

"OK but am I still going to be able to use your breast as my pillow if I stay here much longer?" he joked.

"Sure, if I'm going to be permitted to use that thing as a weapon in case anyone breaks in." She said pointing at my cock.

"It's all yours to use any way you'd like," he said suggestively.

I had never seen nor did I believe there were any cocks as big as his. I asked him,

"Do you have any trouble hurting women when you have sex with them?"

"Not any more. I did with the first couple of girls I had sex with. They were both virgins and it hurt them a lot. After that I learned how to go easy and only go in as deep and as fast as the women were comfortable with."

"Leah, the way you are staring at it makes me think you would like to try it. Am I right?"

"Geez, Matt. We're brother and sister. That wouldn't be right."

"We are also grown adults and able to do whatever we would like and please tell me what's the problem if you would like to have sex with my cock and I would like to use your tit as a pillow." He stated very eloquently.

"I guess you're right." As I kept staring at his cock.

He couldn't help but notice my gaze and reached out and took my hand and moved it to his cock. I was too embarrassed and nervous to look up at him but unwilling to move my hand away from where he put it. I let my fingers uncurl and wrap around his shaft. I could feel him twitch as I did that.

I thought he would reciprocate by putting his hand on my breast but he didn't. He put it right between my legs and was just resting it on my mound. I then felt his fingers start to move a little and realized he had pulled my panties off to the side and his fingers were opening my pussy lips. Oh God, this was really going to happen. I looked at the huge purplish head of his cock and there was a little pre-come showing on the tip. I wanted to lick it off but was afraid to make that kind of first move.

The next thing I knew was he had used his other hand to push my top aside and had his hand on my breast with his fingers lightly massaging the nipple. That, along with me holding his shaft, was beginning to have the expected effect inside of me. I could already feel the pressure growing and I hadn't even felt his wonderful cock inside of me yet.

He lowered his face to my chest and had dropped his mouth to my nipple. Damn, his tongue was active. He then stood up and pulled down his boxers and reached over to me and hooked his fingers under my panties and pulled them down and off in one smooth move. I squiggled out of my top to free up both of my breasts for his mouth.

He lay on his side with his mouth facing my pussy and his cock facing my mouth. I didn't know if he was trying to encourage me to take it in my mouth but all I wanted to do was to run my fingers all over it. I first started to trace the bluish veins laced up and down the length of his shaft and I let my fingernail trace each one of them. I then used my fingers to trace the ring around the head of it while letting a few fingers smear the pre-come all over the head. While this was going on his fingers were very busy opening my pussy lips and searching out my hooded clit. It didn't take him long to find it and then massage the nub out from under its sheath. He then leaned over and let his tongue flick back and forth over the very tip of it which was beginning to drive me over the top. I didn't want to have an orgasm until I felt the ecstasy I knew his monster cock would give me when all, or part of it, was buried in me.

He sat up pulling his cock away from my face and then swung his legs around so we were face to face and said,

"Leah, I didn't bring any condoms."

"Don't give it a second thought Matt. My ex wanted kids and I have been tested over and over again and I am sterile."

He rolled on top of me and leaned down to give me a huge tongue-searching kiss. While the kiss was in progress I felt the head of his cock starting to open up my pussy lips. It was soon in me a few inches but I knew the rest of it might cause me some difficulty. Sure enough he kept up a slow and easy push and I could feel my pussy spread wide with some pain starting deep inside of me.

"Matt, hold it right there for a while and let my insides get used to the intruder."

"Sis, I don't even have half of it in you."

"Holy shit. I thought you were almost buried." I exclaimed with a little fear in my voice. Was I going to be able to take all of it?

He leaned down again and kissed almost every inch of my face. When he got in the area of my mouth his tongue darted between my lips and my mouth automatically opened to receive it. He had one hand still massaging my breast and it felt terrific.

"Try some more Matt." I told him,

I could actually feel the bulbous head of his cock opening up my vaginal canal as it found its way deeper inside of me. My pussy lips were grabbing his shaft ever tighter as his shaft penetrated me. He stopped for a minute or so before continuing with his pressure and then all of a sudden I could feel him hit something that was preventing any further penetration. Neither of us knew what it was but he kept up a very slight pressure and whatever it was blocking him slid out of the way and his penetration continued. Wow, this felt wonderful. He gave one final push and announced,

"It's completely buried in you Leah. How does it feel?" he breathlessly asked.

"Hush up and get it moving." I instructed.

He then started a very slow and very easy thrusting. He would back out of me a few inches and then drive it back in. He kept that up going out a little further with each stroke until he was almost removing it from my pussy before driving it all the way back in me. I never knew how wonderful getting fucked with a huge cock could feel. I used to love sex with my ex and his cock wasn't half as large as Matt's so this monster cock was going to drive me over the top very quickly.

My legs were soon wrapped around his back pulling him even deeper inside of me. I had lost almost all control of myself and could hear noises coming from my mouth I never heard before asking him over and over, "Matt, fuck me, please…fuck me."

Wow, did he ever listen and listen well. He was soon driving his cock into me like a pile driver. In and out, in and out with enough force that I felt it would be poking through my back if he kept it up that hard. It didn't take much of that before I was actually screaming with pleasure as I climaxed. Not just moaning but screaming. He lowered his mouth to kiss me to hush me up when I felt his cock pulsing in my vaginal canal. He was shooting his load deep inside of me and my own juices would be meeting his as they ran out of my pussy together.

He let it slip out of me and lay back on the bed beside me. I leaned up and then moved my face down to his crotch taking his softening cock in my hand and proceeded to lick his cock clean. I then took just the head of it in my mouth and clamped my lips while milking the rest of his juices out of his shaft and taking them in my mouth where I swallowed every drop.

"Holy shit Leah, where have you been all of my life? I never felt anything like what you are doing to me."

I kept right on doing it but swung my crotch around to his face to let his mouth have its turn at my pussy. I wanted to feel his tongue search out our juices running out of me. He sure got the message for I could feel his tongue working my clit over and then diving as deep in me as it could reach. If he kept that up very long I would be having another orgasm.

This all lasted another five minutes or so before we both lay back panting hard and trying to come down from our orgasmic highs. He had moved around so we were face to face and he held a tit and kissed me saying, "Leah, that was wonderful beyond description. I honestly never felt anything like it before."

"Well, bro. With that cock of yours it's easy for me to say the same thing. I have never known fucking could be so awesome."

We lay just holding each other for some time before drifting off to sleep.

The next morning had me ready for another introduction to his cock. He was still asleep when I awoke and I reached over and slid my fingers up and down his shaft and then leaned down and took the head of it in my mouth while jacking his shaft with my hand. His moans started almost immediately as his cock was getting harder by the second.

He tossed the covers aside and said,

"Leah, get up on your hands and knees and let me fuck you that way. It will feel totally different as the natural curve of my cock pushes into a different part of your pussy."

I did and without any foreplay he was right behind me and just lightly pushing his cock against my pussy lips. I must have still been wet from the night before because he slipped in the first few inches very smoothly. He then held my hips as he continued the pressure and this time he slid in me all the way without hitting anything to stop him. Damn, he was right. The head of his cock was touching someplace inside of me that was pure virginal. He then started his thrusting slow and easy while building to deep and powerful thrusts. It wasn't long before I was throwing my ass back to him as hard as he was throwing his cock forward to me. This felt so good I never wanted it to end.

My orgasm rocked me. My big tits were flattened against the bed and my face was turning from side to side as the pulsing overtook me. I had started my screeching again as the pulsing in my pussy was grabbing his cock and pulling it deep. I finally exploded with one tremendous backward thrust and let out an ear splitting howl as it happened. He pushed down on me forcing my face deeper into the bed to try and quieten me. It worked … a little.

He shot his load deep in me and it was soon running out of me the way it had done the night before. He slipped it out of me and then turned me over to say, " Honey, we are going to have to find a way to tame your screaming when you come. I'll be amazed if hotel security won't be knocking on our door to find out if everything is OK.

Sure enough, shortly afterwards there was a soft knock at the door. Matt yelled. "Coming. Hold on"

"Get something on Leah. He'll want to see you before he believes everything is OK." He whispered.

He pulled on his boxers and I pulled on my panties and nightgown top and he went to the door.

"Hotel Security. I'll need to come in." Holy shit, it was a female voice. He looked through the peephole and sure enough a lovely young thing was on the other side of the door.

He opened it and was greeted with,

"Good morning sir. A scream was reported being heard coming from this room and I need to check and see if everything is all right."

She entered the room and saw the bed in a turmoil and me sitting on the edge of it just smiling.

I ended the investigation with, " I can assure you that everything is quite all right," with a huge smile and nodded at Matt. The security officer turned to look at him and her eyes dropped to his boxers and once again, his cock was protruding out from the fly. Soft, but still hanging out six or seven inches.

Security ended her visit with a huge smile saying, "Oh, I can see that everything is just fine. Have a great day." as she turned to me with a huge wink as she left the room.

I got to laughing so hard I had to run to the bathroom before I pissed the bed.

"Matt, her eyes almost bugged out when she saw the size of your cock hanging out from your boxers. I'll bet if you made a move on her she would be on top of you in a flash."

"Oh shut up. It was all your fault with your screaming."

"OK Grouch. Let's go get ready to see more of this wonderful city."

We spent the next several days seeing a lot more of the city and even hit a couple of Broadway shows. The tickets were paid for one of the shows as part of the all expenses paid bit of the trip but we had to pay for the other one ourselves.

The night before leaving New York we tried a different way with sex than we had so far. Matt was going to lie on his back and I was going to sit on his cock. We hadn't been doing anything up until then that evening so I made sure we had enough foreplay that I was going to be wet with my own juices. There wasn't any way I was going to let him drive that thing into me dry. I knelt over his cock while he held it totally erect with one hand and then I dropped ever so slightly to the point where the head of it was just opening my pussy lips. I kept on dropping until I had the whole thing buried and then just smiled at him and taunted him with, "I knew I could do it without your help"

I made him lay perfectly still while I fucked his cock by riding it the way I would a horse. All the way up and then dropping back down hard. When I had it buried I sat on it and squished it around so my clit was getting massaged with his pubic hair. It felt wonderful. I could hear his breaths coming faster and he was starting that cooing noise he makes when he is close to having an orgasm. That made me ride him faster, higher and deeper. Then it wasn't just him who was getting excited… I was ready to blow my top with one huge orgasm. By the time I got "I'm coming," out of my mouth I was right in the middle of exploding. My juices were flowing big time and it was right then he shot his load. I let myself fall forward and we just held each other until we fell asleep. I awoke a half-hour or so later and just slipped off him and lay by his side for the rest of the night.

The ride home was uneventful other than we had a long conversation about our future together. There wasn't any question about the love we had for one another. We are brother and sister but that love is a whole lot different than lovers feel towards one another. And we had certainly become lovers during the last week. I told him I hadn't had any sex at all ever since my divorce and if he and I were going to continue with what we had been doing for the last week I was certainly hopeful he wasn't going to be fucking around all over town. He told me, and I believed him, he hadn't had any sex for months and had no intention of having anyone besides me in the future. We agreed we would let the other know if we had any desire of going to bed with anyone else before we did it.

Things went along great for the next several months. Very few people knew we were brother and sister so we could go anywhere without any finger pointing taking place when anyone saw us. The sex only got better as we explored different things together. I had one huge problem in that I couldn't give him a proper blowjob. I could barely get the head of his cock in my mouth never mind any more of it. When I would get the head in I would lick the head and the tip and then just jack him off so he could shoot in my mouth. Oh, he had orgasms but it wasn't the same as a normal blowjob.

A few months later I had heard of a great resort up in the mountains that sounded like a great place for a min vacation. I called and made the reservations and then called Matt to tell him about it. He had no problem with my jumping the gun without discussing it with him first. We would be going for a long weekend.

The weekend was going to be great fun. I had worked it out so we had a cabin right on the water at Lake George, NY. It was for late October and the weather up there at that time of year is a little on the nippy side, which only added to the attractiveness of it. The cabin had a huge stone fireplace and would be stocked with enough firewood to let us have a fire every afternoon and evening. The cabin also had central heating so the fireplace wouldn't be needed if we didn't want to mess with making fires. We could hardly wait.