Family Feelings

Later as we undressed for bed, Cynthia came over and kissed me. "Don't me so mad. I told you I was going to try my luck. I didn't know you were so jealous. But I'm going to make it up to you if you're game. I told Ron I was going to come to his room tonight, so what we'll do is this. You can wear my nightie and perfume, and put your hair up. I've been wearing this scent all day, so even a guy ought to remember it. If you keep the lights off and don't talk, I'll bet you can get in bed with him. He seemed to like me sucking him off, so maybe you can try to do that. But don't blame me if he ends up fucking you and popping your cherry."

This seemed like a great plan to me. At that moment I would have agreed to anything. "What are you going to do?"

"I thought about fucking Paul again, but that can wait. I'm going to watch you and Ron to see what happens. But remember, this is your show. I'm not coming to your defense if you get more than you bargained for."

Later, dressed and perfumed, I crept down the darkened hallway to Ron's room followed by Cynthia. The door was closed and the lights were off. I opened his door and peered inside. Moonlight streamed through open windows. I could see Ron dimly on his bed, apparently waiting for Cynthia. He was naked, and stroking his erect cock slowly. Seeing my shadow in the doorway, he reached over to turn on the bedside lamp.

"Leave the lights off," I whispered, hoping that he wouldn't recognize my voice. I glided swiftly over, climbed on the bed, and immediately lowered my lips to his groin. Taking his cock gingerly in one hand, I guided the head to my lips. This was the first time I had touched a man's cock, and the feeling was so erotic that I felt my cunt start to moisten. Running my lips around the head, I marveled at how soft the skin was.

"You're in a big hurry, aren't you?" Ron whispered. With his hands he guided me so that my legs straddled his neck. Pushing the hem of my nightie onto my back, he applied his lips to my slit, and let his tongue wander from my asshole down to where it parted the folds of my cunt. Although Cynthia had so often done the same, I felt completely different. Ron's cheeks were slightly rough and scratched the inside of my thighs. I needed to pay attention to his cock in my hands and mouth as well. Cynthia and I had played games with her vibrator in the past, so I had some idea how to give head. However, the cock I was playing with was warm, and much bigger around than that toy. All of these sensations were so novel and exciting that I came suddenly, dousing Ron's lips with my fluids. This seemed to set him off as he began to thrust up with his hips. I tried to keep up with him, licking the head of his cock as he pulled out, and trying to take as much as possible in my mouth as he pushed up. I could see that his balls were drawn up tight, and I touched them lightly, feeling the soft crinkly skin of his scrotum. Remembering something Cynthia has told me, I let one finger down to the base of his balls and pushed.

This stimulation had an effect. Ron took his mouth from my cunt, and gasped, "Fuck, I'm cumming". The first spurt went deep to the back of my throat, causing me to cough. I took my mouth from him and the next glob of cum hit me on the nose and upper lip. Recovering my composure a bit, I made little pumping motions along the shaft and head as more of his semen oozed from his cock. I licked each drop off, savoring the slightly salty taste. It was different from a woman's taste, and I decided then that I liked it.

Sensing that the cock in my hand was softening, I gave it a final lick and kissed its head. I turned around to see that Ron was lying flat with his eyes closed, breathing hard. I moved up to him and kissed him with my cum-drenched, then ran out of the room.

Rushing back to my room, I found Cynthia on her bed, legs spread, working her hand into her pussy.

"I did it," I whispered.

"Fuck yes you did. I was watching the whole time. You were so hot. That was the first time I ever saw another girl and a guy. I just had to make myself cum." I got on the bed with her and kissed her mouth. The man-scent on my breath seemed to bring her to climax, as she pushed her tongue against mine.

"Let's try it again tomorrow night with Paul. See if you can set up a date in his room like tonight." I had decided to myself that if I could manage it, I would let Paul fuck my pussy. I'd had enough of being a virgin. Giving head to Ron had convinced me that sex with a man could be as exciting as with Cynthia.

"I'll see what I can do. Based on this afternoon's experience, it shouldn't be too difficult."

The next day passed slowly. Both of the men went into the city to work, and Cynthia and I spent the afternoon horseback riding. The feel of the saddle between my legs made me horny as I fantasized about the evening's adventure to come. I resisted bringing myself off since I wanted to save up for Paul.

Finally the hours had passed and, when eleven in the evening finally rolled around, I was dressed in Cynthia's nightie and smelling of her perfume. Cynthia and I snuck down the hall to Paul's room. This time the lights were on. Cynthia opened the door and poked her head into the room. "Turn off the lights, Paul. It's more romantic in the moonlight."

When he had done so, it was I rather than Cynthia who glided into the room and onto Paul's bed. He was reclining propped up on a pillow. I immediately dove down to his waist, hiding my face. His cock was only half-hard, so I occupied myself as I had with Ron's, taking it gently into my mouth and licking slowly just below the head. He started to swell immediately. I was on my knees beside him with my backside facing him. This gave him easy access as he slowly stroked my buttocks and between, passing over and around my asshole and then down to probe my pussy, which was sopping wet.

"Mmmmm," he said as he hardened to full length. I couldn't get him entirely in my mouth, so I rolled my lips and tongue over the head, and then licked down the shaft to its base. He placed both hands on the globes of my ass and leaned forward to kiss between my legs. I swung one leg over him and spread myself as wide as possible over his body, giving him full access to my innermost depths. I looked up towards the door, which was cracked open. Knowing that Cynthia was watching us gave an extra fillip of pleasure to what I was doing.

Paul's cock began to ooze slightly. I imagined that this was the pre-cum which Cynthia had once explained to me. When I felt his tongue probing my asshole as his fingers circled my clit, I came at once with what seemed like a veritable flood of juice streaming from me.

"I think you're ready, eh? Let's do it doggy." Paul whispered.

"Yes! I'm ready," I thought to myself. "I'm finally, truly ready." The doggy position was ideal as I wouldn't have to face him, so the risk of my identity being discovered seemed remote. I raised up to support myself on my knees so that he could crawl out from under me, and I pulled the nightie over my head and threw it to the floor. I felt his belly lean against my buttocks as he slid his cock against my back and then down along my slit. His hands lay lightly on my hips as the cock head made teasing touches up and down. At one point, he rested it against the opening to my ass, and I wondered if he might be thinking of putting it in. Finally he placed the head between my lips at my sopping opening, and pushed in slowly.

Although my cunt was super-lubricated, he had some difficulty entering. I felt the cock head spreading my lips apart and pushing against the inner walls. "You're really tight," Paul said. I wanted him to push it all in with a single thrust, ridding me of my troublesome maidenhead once and for all. Paul had other ideas. He seemed to like the resistance and made tiny pushes in and out, each time gaining a fraction of an inch.

After what seemed an eternity, I felt the head push against my hymen. Sweat beaded my brow. "Do it," I thought. "This is it. make me a woman at last." But it was not to be.

"Fuck!" said Paul. He pulled out abruptly and switched on the light. The masquerade was over.

"What the fuck are you doing," he shouted angrily.

I wanted to say, "Trying to fuck you, my dear lovely brother." But all I managed to do was cry. I put my arms around him and whimpered, "Don't me mad at me. I'm sorry. I thought you'd like me. I love you." Now Paul is a really kind-hearted man, so my tears and supplications left him at a loss. He knew he should be furious at me, but the fact that he was naked holding a crying naked woman in his arms made a situation for which he was totally unprepared. I noticed that his erection seems as hard as ever as I pressed my tits against him.

"You're acting like a silly kid. How could I live with myself, knowing I've taken your virginity? Get the hell out of here!"

"Wait here a minute. I want to show you how I really feel about you." I ran out of the room, buck naked, and rushed back to my room. Cynthia had seen the whole scene and followed me. I grabbed Cynthia's vibrator and ran back towards Paul's room. When I arrived trailed by Cynthia, Paul and Ron were both there, and Paul had put on a pair of briefs. His cock was still engorged as evidenced by the protuberance that showed through the cloth.

Ron's eyes widened as I stormed through the door, vibrator in hand, naked as the day I was born.

My speech came out as if I had rehearsed it a hundred times. "You guys make me so mad I could bust. What's the matter with you? You must be faggots or something. Isn't my pussy pretty enough for you?" I sat down on the bed and spread my legs for them. "I think mine is as pretty as Cynthia's, and you didn't have any trouble with fucking hers. Look! Mine fucks just as nicely."

I glided the tip of the vibrator between my lips and stroked it in and out. I could feel the tip contact my hymen each time. Cynthia and the two men stood there speechless watching me.

"Fucking a virgin isn't so hard either. Just watch!" Closing my eyes, I forced the vibrator deep into me, feeling my hymen tear. There was a sharp pain, but nothing more. I left the toy buried in myself for a moment, then pulled it out slowly. A few streaks of blood showed on it. When it was out, I threw it into a corner.

"There! I'm not a virgin anymore. I told you I loved you and I hope I proved it. Now finish making me a woman."

Paul put his arms around me under my arms and picked me up, showering my face with kisses. I wrapped my legs around his waist as I met his kisses with mine. I somehow managed to notice that Cynthia and Ron had quietly left the room and closed the door.

Lowering me to the bed, he dropped his briefs to the floor and kicked them away. "Susan, my dear, dear sister. I've always loved you too. And yes I did want to make love to you. But I couldn't make myself deflower you. Since you made such a sacrifice yourself, I won't refuse you any longer."

I scooted back on the bed and propped myself on the pillow, spreading my legs wide. A few droplets of blood stained my pussy lips. Ron put himself between my legs and gently spread my outer lips. "Does it hurt?" he asked gently.

"A little. Not too much. Please do it. I want you so much."

He moved up towards me and put my legs over his shoulders. Holding his cock in one hand and opening my cunt with the other, he guided the cockhead to lodge at the opening where it had already been not so long before. This time, he leaned forward in a slow steady movement so that I could see the shaft disappearing into me a little at a time. When it arrived at my shattered hymen, I flinched a little, but the pleasure I was feeling overcame any pain. At last he was completely buried in me, his pubic hair meshing with mine. The sensation of fullness was incredible and I could feel my tunnel squeezing his shaft like a glove.

He moved in and out very slowly and sensually for what seemed like an incredibly long time. His lips were pressed to mine as our tongues danced around each other. Next he accelerated his motion so that he was almost slamming into me. I came hard. He slowed down to a steady pace for a while longer, then buried himself and stopped.

"How do you like that?"

"Oh God, it's better than I hoped. Can you fuck me hard and fast again?"

"Yes but I'll cum. I'll have to pull out."

"I'm on the pill. I want to feel your cum inside me. Fuck me hard now."

Paul needed no more encouragement, and began to plow into me as fast and deep as he could, and I pushed back to him on every thrust. Then I felt him tense and he buried himself as his cock spewed into me. At each spasm he made a little thrust against me, so I he must have had six or so ejaculations.

We rested a few moments. Putting his arms under me, he rolled us over so that I was lying on top of him with his cock still buried in me. I undid my hair so that it fell down over his face. Our lips met in one more deep kiss while I sensed his cock soften and fall out of me. A trickle of fluid seeped out of my cunt and onto his belly and the bed sheets. I rolled off of him and saw that his cock was stained with a shiny mixture of semen, my juices, and a little blood.

I picked up the nightie and pulled it over my head. Paul gazed at me from the bed as if he couldn't believe what had just taken place. I leaned over to kiss him, "I want to do this lots more times. We have all summer to practice." With that I ran out of the room and back to mine.

Cynthia wasn't there, so I took a long hot shower. It's hard to describe the feelings of fulfillment I felt. A woman at last, and with the man of my dreams.

...

I could go on at great length about all that happened that summer, but this story is already too long. Having yielded my first maidenhead, more or less, to Paul, I felt obliged to yield my second to Ron. Neither my brother or cousin had ever had anal sex before, but they both came to love it as much as I do. Paul took Cynthia's second cherry the same night that Ron took mine. The four of us seemed inexhaustible all summer, and every evening was the scene of our private orgies.

All good things come to an end, and Cynthia went off to college while I had yet another year in boarding school. Luckily for me, Paul and Ron proposed that they could come to escort me on weekends, so that our unsuspecting parents left us free for weekly sessions, most of which were spent entirely in bed.

After graduation, we had another glorious summer of sun and sex. Then I went off to Paris to study art for two years. I had promised myself never to have another man other than Ron or Paul, but I was able to meet any number of women with the same "tastes" as me. Cynthia came over for a visits, and Paul came several times as well.

If you've read Sonia's story, you pretty much know what's happened since.

All contents © Copyright 1996-2024. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+1f1b862.6126173⁩

We are testing a new version of this page. It was made in 460 milliseconds