Lysa's First Time

This is my first time doing anything like this. My boyfriend found this site and we have really loved some of the stories. I decided to write about my first time. It was rather unconventional and I had several firsts in a short period of time. I hope everyone likes it. I have a few more experiences that I’ve had since then and am eager to write about those.

I couldn’t wait. My parents had gone away for the weekend and left my brother and me alone. Even better, he was going to sleep over a friend’s house. My boyfriend, Jeff, was coming over to spend the whole weekend and ravish me. We had planned this to be my first time since we heard that we could have the house to ourselves. If Jeff would have his way, we wouldn’t be dressed at all for the two days and I was determined he’d have his way.

We had been dating for over a month and all we had been able to do with each other had been some mild foreplay during our rare make out sessions. We both lived with our parents and siblings, so we could never get any time alone to get more serious and we had yet to see each other completely naked. To say the least I was getting anxious to see him naked and spread my legs for him. I fingered myself to sleep every night since I met him just thinking about finally being able to see his whole cock, easily 8 inches, dangling in front of my face. I had been saving myself for someone like him and for a weekend like this.

By early Friday afternoon my parents had already gone. I called Jeff and told him to come over. A few minutes later he arrived and we went up to my room. I told him to wait there while I showered and got ready for the big moment. I know Jeff had been with at least two girls before me, one was my friend, so he was a bit more experienced and told me that he preferred me shaven, with a small patch left close trimmed. It took me longer than I thought to get it the way he wanted.

When I finally got out of the bathroom, Jeff was gone from my room. Looking all over the house, I heard a noise from my brother’s room. He was a year older and had the room over the garage. Apparently he didn’t leave for his friend’s yet. We were pretty close and I was friends with his current girlfriend, so when I pushed the door slightly ajar I didn’t know what to think. There was Jeff standing with his pants around his ankles kissing my brother, who was pulling at Jeff’s huge, semi-rigid dick. Jeff, in turn was doing the same to my brother, who had no clothes on, with one hand and grabbing his ass with another. I felt surprised, disgusted, disappointed and excited all at once.

They didn’t seem to notice me at first, then my brother opened his eyes and saw me standing in the door. He immediately released Jeff and grabbed the sheets off his bed to cover up. Jeff looked a little embarrassed, but not as much as I thought he should. My brother yelled at me,

“What are you doing?”

With that I got over the shock and yelled back the same. Then I looked at Jeff and felt about to cry. He must have noticed and said not to be sad. That we were still going to do what we planned.

“I was getting horny and just couldn’t wait. Besides I was curious to find out if what I heard about your brother were true. A few people have been saying that he goes both ways and the thought of getting the two of you together was too good to pass up. I asked him about what I heard and he said he was hoping I’d ask, and him and Stacey were talking about asking me to join them tonight. When he saw me in your room we both figured to go for it.”

While he’s explaining this to me I noticed that he was getting harder. “So what do you say? Your brother’s up for it if you are.” It took me a minute to think about it. I mean I was up for Jeff, but my brother!? Then I looked over Jeff’s cock again, dripping precum. There was no way I was going to pass that up. I said I’d do it, but with conditions. I don’t touch my brother and I get Jeff first. They both agreed and with that Jeff stripped of the rest of his clothes and walked over to me. He kissed me on the lips softly and put a hand on one of my 34c breasts. I pushed my body against his. His dripping penis pressed against my stomach.

The sensation of it rubbing on me almost made me lose it. He then picked me up and carried me to my brother’s king sized bed. Chris, my brother, pulled the covers off and Jeff lay me down. I was able to finally appreciate Jeff’s nakedness. He was near perfection. I saw him looking me over too, especially my shaved pussy. We stared at each other and my brother looked on at both of us from the far side of the bed stroking his own impressive member. Almost instinctively I reached a hand between my legs and traced the folds of my burning pussy while my other hand pinched my left nipple.

Jeff climbed over me onto the bed and was now between me and Chris, but facing me. His cock rested on my leg and continued to drip silver drops of precum. He started moving a hand over my breasts, down my stomach and to my mound. I closed my eyes and spread my legs to accommodate him. He moved his hand down and gently parted my cunt lips and easily slipped his finger into my soaking hole. I let out a gasp at first and then a sigh. He started moving his finger from my hole to my clit, letting my juices lubricate my hairless pussy.

While he did this, I reached over for his dick and started to rub it. We both built up a rhythm and we were soon pumping our hips to meet each others hand motions and I could feel myself getting ready to come for the first time this weekend. Chris must have been getting hot too. He shifted on the bed for a better view and was stroking himself furiously. The site of that and taboo thought of my own brother jerking to the sight of his little sister like this drove me over the edge. I began whimpering and then tightened my whole body in convulsive spasm. My legs clamped Jeff’s finger inside me.

Once I came down, Jeff removed his finger and moved down my body to eat me out. He was expert at this and really enjoyed doing it, more so it seemed, that I was shaved. First he licked clean the cum that flowed out of me from the orgasm, but that drove me to another in about 30 seconds. He then he propped his ass in the air for better positioning and tongued my clit. This was better than any other time we had done it. I came with a shocking orgasm followed by waves of smaller ones. I was getting so hot, I started to talk dirty to him.

“Lick me…lick my pussy. I’ll do anything, just keep making me come!”

I couldn’t believe how horny I was feeling. The more I came, the more I wanted. I pulled my nipples until they hurt and threw my head from side to side.

“I’m your whole!” I kept yelling.

That was more than Chris could take. He got up on his knees next to Jeff and let out a deep, long sigh, shooting his load onto the bed. Some shot out onto Jeff’s upturned ass and back. My brother kept shooting loads of cum out, the sight of it drove me wilder. Jeff tried to stop for a moment to wipe Chris’s mess off, but I grabbed his head and held him to my cunt.

“Don’t stop!” I yelled. I felt the biggest orgasm I ever had building up.

Chris got up to get a towel for himself, but to my surprise, he was still hard as a rock, when he got back.

He said, “If you not going to let Jeff stop with you maybe I should take care of him for a while.

He then put his hands on each side of Jeff’s ass and began to lick off the cum he shot there, then proceeded to lick his asshole. Jeff moaned into my cunt pushing me over the edge. This was it.

“Fucking yeah!!! Lick it, do it!!!”, I screamed.

I wrapped my legs around Jeff’s head shaking, while Chris continued to rim him. Jeff was moaning more and then Chris reached between Jeff’s legs and started stroking him as best he could. Jeff pried his head from my legs and told me to climb under him with my head between his legs so I could suck him while Chris worked his ass with his tongue.

I saw this position on a video once and wanted to try it. The most I could fit in my mouth was the head of Jeff’s dick and some of the rod. I loved the taste of pre-cum since the first time I tasted it. I hadn’t tasted cum yet, but knew I would soon.

From my angle, I could see Chris licking away at Jeff’s ass. From time to time he would fondle his Jeff’s balls. I couldn’t take my eyes off the site. I could feel I was about to orgasm again and braced myself. As waves of electricity washed over me, I moaned around the purple swollen head in my mouth and gripped the shaft with my right hand. My left one worked one of my nipples. A few seconds later, I felt Jeff cock begin to swell more and his body tense up and I knew what it meant. I had just enough time to take a deep breath when I felt the blast of cum into my mouth and down my throat. So much so that I had to pull him out of my mouth.

I continued to stroke him and was rewarded with more cum exploding onto my face. After about a minute more, Jeff shifted to my side and lay on his back. Chris moved up between Jeff’s legs to get what cum was left in him as I looked on fascinated at the site of my older brother sucking on my boyfriend.

We both then moved onto each side of Jeff and he put his arms around us to pull us close. After resting a few minutes Jeff became hard again and asked if I was ready to become a woman. I smiled and said in a half-voice “yes”. The only way I can explain the sensations I was feeling would be to say that I felt like I was on some type of drug. I never wanted the feelings I was having to stop and the more I felt the more I wanted and wanted to do.

Jeff rolled on top of me and placed the head of his penis at my pussy. I was still soaked so he started to slip in easily. Once the head was in I began to feel the stretching of the walls and the mix of pain and pleasure. I gripped his arms and winced. He stopped pushing in until I told him he could slowly proceed. My friend Gina told me that it would hurt the first time and Jeff’s size added to the discomfort. With Jeff buried about half his size in me, I felt immense pressure. I told him to pull back and then to build up a rhythm before trying to break my cherry.

He began to pump in and out of me. The more he did the less it hurt and soon I was pushing forward to meet his thrusts. I was breathing heavy and moaning his name and then I felt it happen. A quick pain, like a hard pinch. Jeff slowed down and was very gentle with me. We looked deep in to each other’s eyes and then kissed long and hard. I could hear Chris next to us climaxing again and that pushed me over the top again. This one was different though. Jeff was in me for this and a great sense of emotion came over me and I started to cry a little. At first Jeff stopped, but I told him to keep going.

“ It just feels so good, don’t stop until you’re done. I want you to fill me up.”, I said.

Not long after, Jeff let out a long sign and his cock twitched and throbbed inside me. I felt the cum leaking into my ass.

He stayed in my cunt until he was soft and then moved off me. We kissed some more and then both went to Chris’ bathroom to clean up. I told Jeff I need to take a shower, so he said he’ll go wait with Chris until I was done. I closed the door, leaving just a slim crack where I could still see the bed without being noticed and turned on the water.

Jeff and Chris wasted no time. Chris was the one to make the first move.

“So you’re curious about being with me? Since you had all the fun with my sister, I get to have fun with you.”, he said.

Chris then stood on the floor and walked around the bed to Jeff. They both opened they’re mouths and started kissing and rubbing each other. Chris then pushed Jeff onto his knees, grabbed the back of Jeff’s head and put his dick in Jeff’s mouth.

“Suck me hard you little bitch. Since this is your first time with a guy, you’re my little bitch.”

Jeff loves dirty talk, and Stacey said Chris does too. Jeff wrapped his hands around Chris and kneaded his ass. I could see he was talking most of Chris and must have loved it because of the moaning noise he was making.

“Oh Jeff, yeah, you’re good at this. You’re a natural cocksucker.”, Chris hissed.

“OK get up and bend over the side of the bed.”, Chris ordered Jeff, who eagerly complied.

I felt light headed from the thought of what was going to happen next. I never saw anything like this ever and now here was my brother standing with his dick in his hand getting ready to butt fuck my beautiful boyfriend. Chris opened the dresser next to the bed and took out a tube. He squeezed some of the contents into his hand and rubbed it on his cock. Then he took a finger and slid it into Jeff’s asshole. Jeff let out an, “OOOOOOO” as Chris worked the lube into him. He went from one to three fingers before he finally inserted his dick into Jeff. They both sighed when he entered, and then stood motion less about a minute.

Jeff said, “I can feel you throbbing in me. This is incredible.”.

“You haven’t felt anything yet!” Chris told him, then he started to push deeper. He thrust forward into Jeff with pulling back. His hips hitting Jeff’s ass cheeks. His pace moved faster and they were breathing heavy.

Chris asked Jeff, “ Let me know when your ready for more little bitch. Then I’ll start to really fuck your ass, you fucking boy pussy.”

I’ve never heard anyone talk like that, but Jeff looked like he liked it.

“I’m ready for you baby. I want all you’ve got.” Jeff said breathlessly.

So Chris pulled out of Jeff and told him to get on the bed on his back and to bring his legs up. Soon my brother mounted Jeff like Jeff had done to me. I fingered my clit trying to hold off the climax until they came. Chris pushed deep into Jeff causing him to yell out and wince. Chris didn’t slow down though. He started ramming into Jeff’s ass relentlessly. Chris reached to Jeff’s dick and stroked it.

“ Take it like a whole, baby! You’re my whore now! Beg me like a slut. Beg me to keep fucking your ass!”, Chris ordered

“Make me your whore! Fuck my ass hard! Fuck it hard…I love you in me! I’m going to come soon. Jerk my cock and fuck my ass! Oh Chris!”

I couldn’t take any more myself and came again and again.

Chris yelled out, “ I’m cumming!” Jeff shot his load too, but Chris just rolled Jeff onto his stomach and pumped into him more.

When I finally went into the shower, Chris was still fucking Jeff. They had finished by the time I had gotten out. By then it was very late and we went to sleep. I dozed off thinking about what the rest of the weekend would be like.