Chapter 1

I grew in a conservative family. My Catholic parents raised me and my three sisters in a very polite environment. I never heard them speak foul language even when they got mad. So I and my sisters grew shy and prudish.

My eldest sister, April, was five years my senior. She married an equally conservative guy after she got her university degree in physics at the age twenty two. Her husband was a lawyer. My second sister, Eunice, two years my senior, was studying biology. My youngest sister, Lenore, one year my junior, was in high school.

At seventeen, I came to know a conservative Jewish girl and we spent a lot of time together. Although neither of us tried to make a move on the other, I could not help fantasizing about her without changing the nature of our sort of platonic relationship.

Rachel was a brunette knock-out with beautiful, big brown eyes, nice tits and a perfect ass with matching legs. Many guys tried to hit on her, but she never accepted their invitations. We were sort of a nerdy pair and we enjoyed it.

Once I walked Rachel to her sister's apartment and her sister, Raquel invited me in. Raquel was a taller version of her sister with slightly bigger tits. She worked in a law company and lived alone downtown, while Rachel still lived with her parents in the suburbs. Raquel was a nice hostess but not at all conservative. I could see the tops of her tits every time she bent over. She made it a point to show me the tops of her thighs and panties. My heart started thumping and my cock grew into a big boner, forming an outrageous bulge that I could not hide. Rachel looked at my bulge and giggled. I must have blushed into a deeper shade of red than humanly possible. Raquel looked at me with a smile and a mischievous wink.

Rachel was to spend the night at her sister's, so I had to leave alone. Raquel walked me out of the door in her skimpy dress. She said she wanted to see me tomorrow at the same time to talk with me about her sister. She said her sister was going to join us later. When she turned back her ass brushed my not-so-soft bulge, making me shiver.

The next early evening I was knocking at Raquel's door. She opened the door in a light night dress. She had underwear on that did not do much to hide her attractions. She invited me to sit down and offered me a soft drink. Raquel started the talking by asking me about what I thought of her sister and how she did at school and so on. Then she abruptly asked me whether I had sex with Rachel. I collected all confidence and seriousness I could muster and said, "Of course not."

Raquel laughed out loud at my answer. I did not understand.

"Why not? Don't you find Rachel pretty?" Asked Raquel.

"Yes, she is very beautiful, but... , " I said after hesitating a little.

"Aren't you a human? Don't you have human desires?"

"Yes, I do, but..."

"But what?"

"But I do not think Rachel will approve," I said triumphantly.

Raquel laughed and said, "Why not, is not she a human being with desires just like me and you?"

"Yes, she is."

"Then why not?"

I hesitated and said, "Because it is wrong."

"How wrong?"

"Well, we are not married."

"So what? I have never been married but I have been fucked more times than I care to remember and it was very right to me. I enjoyed it very much. Hell, I can't live without it."

I did not answer.

"It is for your own good, yours and my sister's, that is. You are young and youthful, you should enjoy yourselves. Experiment and live your lives. You will love it, both of you. I will talk with my sister tonight and let her go on the pill, but you have to make the first move in a couple of days."

Raquel paused a little then continued, "I liked the way your cock bulged yesterday when you looked at me and I know the look Rachel gave your bulge. She is interested, but she is too shy to show it."

"Now," Raquel continued. "I will show you this," she said, inserting a cassette into the VCR. She sat beside me and pressed the play button on the remote.

The scene started with a couple kissing. It developed fast into cock sucking and pussy licking. I was shocked to watch this, but my cock was harder than ever. While consumed in watching the sex scenes before me, I only noticed when my hard cock popped out of my fly. Raquel was kneeling between my legs.

"What a pity," she said. "to leave such a beautiful cock hidden inside. Your cock must be worshipped and enjoyed." Her talk made my cock grow harder. She bent her head down and started licking the head of my cock, making it jump with delight. I shivered like a leaf while she mouthed my cock. Before I knew it her lips were pursed around the base of my cock. The couple on the screen were forgotten now. I felt a strong delightful feeling developing. It was in a sense similar to what I felt when I needed to pee but much more enjoyable and it kept going stronger. I tried to pull out, to protest, to say no, to let her stop but I could not. Soon my cock was pulsing as my hot come was pumped into her sucking mouth. She swallowed everything!

I was amazed. I was panting when she looked up at me and said, "Your come tastes so good." I couldn't believe it. She licked her lips and said, "That was quick, but this time you will enjoy it more." I could not imagine anything more enjoyable than what I had just experienced.

My cock started to go limp, but when she flicked her tongue just under the head, it went up rapidly. This time, Raquel took it slow. She looked as if sucking my cock was the most enjoyable thing in the world. While licking my shaft, Raquel worked my pants down to my ankles and off. She then licked my balls and tried to take them into her mouth. It felt great.

She looked into my eyes and said. "You have a lovely cock. If Rachel had it in her pussy, she would really love it." She gave it an audible suck and said, "If you were not my sister's boyfriend, I would have fucked the shit out of you here and now. Now, sucking your cock would have to suffice."

Raquel took her time with me, slowing down whenever I neared orgasm. I pumped two more loads down her throat while watching that two-hour tape. She finished swallowing my last load just as the tape started to rewind.

I put my pants back on. Raquel suggested I leave before Rachel came in since she wanted to talk to her alone. She suggested that I do not try to fuck Rachel just the next time, but that we spend our first session exploring each other's bodies and maybe try some cock sucking and pussy licking. I left with visions of Rachel sucking my cock or fucking me. I went to bed that day with those visions chasing me. I did not know how to face Rachel the next day, but I needed not to worry, it was very normal.

After school, Rachel announced that she had Raquel's key with her and that we could go right there directly, which we did. I could not hide my horniness and Rachel noticed it. I saw her eye my bulge a few times, but she did not comment.

We were nervous, sitting on a sofa in Raquel's apartment. Raquel was not there. Finally, I turned towards Rachel and kissed her. She responded. First we did not know what to do. It was tentative. Then it got smoother and we enjoyed kissing. I lead her hand to my bulge and started stroking her thighs as my mouth traveled down to her neck.

Raquel was self-conscious when I took her dress and bra, exposing her tits, but when she saw my appreciative look, she relaxed. I kissed her pale tits, leaving her dark erect nipples to the last. She gasped when I first sucked her nipple into my mouth. Then Rachel started moaning as I continued sucking and switching nipples.

I pulled her panties down uncovering her fuzzily covered pussy. She was moist there. I kissed and licked tentatively, getting used to the smell and taste. Then I went wild on her slice, licking, kissing and sucking. She went nuts, tightening her thighs around my head. Soon, she was grunting and gasping as her first orgasm wracked her young body. I continued licking gently until her orgasm subsided.

After she recovered, Rachel helped me out of my clothes and started get acquainted with my hard cock. First she held it with her hands, hefting it and feeling up my balls, then she started licking the head tentatively. Rachel was eager to suck my cock. Her lips were tightly stretched around the bulbous head of my cock as she took it in. In a couple of minutes she was trying hard to cram all of my cock into her mouth. She failed of course.

"Rachel, take it easy," I said. "Take your time, this it your first time, just enjoy yourself."

She mumbled something unintelligible and started licking up and down my shaft. Rachel then was content to pump four to five inches of my cock in and out of the hot, wet cavity of her novice mouth. I told her I was close to come. She doubled her efforts.

"Get ready, Rachel," I panted as my cock swelled some more.

Rachel pursed her lips, keeping only the head in her mouth. She sucked hard while pumping my shaft with her hand. She almost gagged when my cum burst abruptly into her mouth, then she started swallowing, letting an elusive drop escape her lips.

"I did it," Rachel squealed happily. "I did it."

"Yes, honey," I said, picking her up and kissing her right on the mouth, tasting traces of my cum on her mouth. "It is your turn again."

She reclined on the sofa and spread her legs. I lifted her legs up, pushing her knees close to her chest. Her pussy and pink puckered asshole were utterly exposed. I smiled at her before I dived in and licked the moisture off her pussy lips.

I pulled back and had a look at her virginal treasures. Her pussy lips were red and hot, blood-engorged with excitement. Her lovely puckered asshole looked like a shy little rose. I gave her asshole a tentative lick. She jumped. "I do not think you should do this," she protested, but looking again at her now moistened anus got me tempted again.

I pulled her cheeks apart and gave her asshole a longer licking. She stiffened for a few seconds, then relaxed and started moaning delightfully. I sat back and looked at her. She looked disappointed that I stopped.

"You like that, don't you, you little naughty girl?" I asked teasingly.

She nodded shyly. "I didn't know I was this sensitive back there," she said weakly.

"Now you know." I said. "You have a gorgeous, edible asshole, do you know that?" I continued. "It tastes good, too."

I went back to licking her asshole. I pushed my tongue gently at her wrinkled opening and it relaxed, taking just the tip in. I licked her orifice circularly listening to her moans. I moved up to her soaked pussy to slurp up her juices and then returned to her shiny asshole. I licked insistently feeling her asshole relax and open up even more. I probed it with my tongue. She gasped every time I pushed my tongue in. I pulled back and had a look. Her asshole was gaping slightly. Like in that porn tape, I wet my index finger with her pussy juices and wormed it into her ass slowly. She gripped on it. I wiggled it and swirled it around, making her relax and then pumped it gently in and out of her anus.

Pursing my lips around her clit, I sucked hard while pumping my finger into her ass. In less than a minute, she was groaning, her pussy pulsing and squeezing juices out while her asshole contracted repeatedly around my probing finger. She came harder than the first time and took a longer time to come down. I smiled at her, my lips covered with her juices. Looking into her eyes, I pulled my finger slowly out of her gripping asshole. It popped out with a plop and her orifice clenched shut. She straightened her legs.

I bent over Rachel and kissed her, coating her lips with her own juices. I brought her attention to my now hard cock and started jerking it over her chest. She replaced my hand with hers and in a minute, my cum was flying onto her chest and face. She raised her head and intercepted my cum with her tongue, then took the head into her mouth to suck me dry while rubbing my cum into her skin.

We rested a little then showered independently. After a while Raquel arrived. We must have looked to her like the cat that ate the canary.

"Hi, guys," Raquel greeted. "You must have enjoyed yourselves. I am glad you finally came around."

We just nodded.

That day, Rachel also was to spend the night with her sister. On my way out, Raquel stopped me out of the door and advised me about my next session with Rachel.

"Make her cum once or twice before you try to enter her," she said. "Prepare her with your fingers too. Don't force it in, be gentle. Please don't hurt her, she is your lover."

"Of course, I won't hurt her," I answered. "Don't you worry, Raquel. I do care about her."

Then I left.

The big day came and we both were eager to get on with our first fuck. I kissed Rachel and then pulled her panties off as she lay comfortably on the bed. A few licks to her pussy got her hot and moaning, then I alternated between licking her pussy and anus while her legs pointed to the ceiling, totally exposing her holes to my hungry mouth and playful tongue. Then my fingers joined in, rubbing her orifices gently before they dipped in. I transferred juices from her pussy to her ass and had one finger sliding to the second knuckle in and out of either hot orifice. Rachel moaned and humped my fingers as my tongue worked her clit dutifully.

Warmed up, her holes relaxed around my fingers but her fresh pussy could not take my finger deeper because of her hymen. Soon I had two fingers working each hole. Her ass could take my fingers all the way in. Rachel's moans and grunts heightened indicating she was on the verge of her orgasm. Closing my lips on her clit and giving a little suck, I sent her convulsing wildly in her orgasm. Her holes milked hard around my sticky fingers.

My cock bounced in front of me as Rachel pulled my pants down and off. She let me fuck her mouth standing beside the bed while she was kneeling before me. Her mouth did not ignore my balls when she jerked my cock gently afraid of making me come before she wanted me to. Then she had me sit on the edge of the bed and lean back. She bent over me and tried to take all my shaft into her mouth. She could not but she was an inch away from success. She worked her mouth up and down my shaft very nicely.

Suddenly, I felt the head of my cock pop past her throat. That sudden feeling made me pump the first couple of jets of my load beyond her throat. Rachel pulled back reflexively and had the presence of mind to stop before my cock was out of her mouth. She sucked on the head and jerked the shaft to get the rest of my load. After she sucked me dry, she gave my cock appreciative kisses and licks until my cock was limp.

I helped Rachel stand up and took off the rest of her clothes. As she stood naked before me, I kissed and licked her erect nipple before taking them inside for some sucking, making her moan and almost lose her stance. I slipped a hand between her thighs and rubbed her pussy back and forth. She humped my hand gently.

Arranging Rachel on her forearms and knees on the bed, I complimented her on her pretty ass and started licking her asshole. The little orifice relaxed and soon I was working two fingers in and out of her anus, reaming out her tight backdoor. She moaned, pushing her ass back to meet every stroke. I got three fingers up her asshole to the first knuckle and was swirling them around and pushing them in further. Her asshole was responsive to my gentle coaxing. I said as my fingers went further inside her, "What do you say, Rachel, we leave your pussy virgin and fuck your gorgeous ass?"

"No, Nick," she said with disappointment in her voice. "I want you in my pussy then I want you in my ass. Please take my pussy first."

"You got it, babe," I said, removing my fingers from her ass. I pulled the lips of her pussy apart and started licking her juicy insides. Flicking my tongue over her clit made her gush hot juices which I spread all over her pussy. I worked her very close to then knelt behind her. I brushed the bulbous head of my cock up and down her crack from clit to anus and back, spreading her juices all over and making her squeeze out more fluids. I pulled her knees further apart and adjusted her back, opening her pussy to the limit.

"Do you want to get fucked, darling?" I teased.

"Yes," she said. "Please fuck me."

"Are you sure?" I asked, tracing the head of my cock around her pussy lips.

"Yes, please," she hissed.

"Ok, babe," I said. "hang on."

I pulled her pussy open and placed the tip of my cock at her tight opening. Holding her hips, I said gently, "Relax and push back, Rachel," and I started pushing forward gently myself. The head went in. Suddenly Rachel sort of jumped and pulled forward. I pulled her back firmly, sending half my cock in. She grunted as her hymen broke. I paused, fingering her clit. Rachel's no longer virgin pussy squeezed my shaft very tightly. I almost came. In about ten seconds Rachel started rocking back and forth gently. In a minute my balls were bumping into her clit as her pussy swallowed my thick cock to the root.

"How does it feel, honey?" I asked.

"Mmm, it feels great," she moaned.

I leant forward and squeezed her tits. Her pussy tightened around me and she almost came. I continued kneading her tits gently and pulling on her erect nipple while delivering long, deep strokes to her tight pussy. Rachel stopped moving and her pussy convulsed around my shaft. I fucked her harder as she went through her orgasm, clawing at the sheets and biting her lip. Her pussy soaked my cock and balls with hot juices. I could not hold back any more, I let go with my come, flooding her soaked pussy even more.

We collapsed on the bed, me on top of her, holding her in my arms. We exchanged sweet words of affection. My cock shriveled and slipped out of her pussy. Her pussy leaked out our mixed come. "Do you have enough strength to go through your first anal fuck?" I whispered.

"Yes, darling," she hissed. "I am ready when you are."

I arranged her on her elbows and knees and wiped her pussy with a wad of tissues. "Is there any butter?" I asked.

"It's in the fridge," she said.

I warmed some butter in the microwave and returned to the bedroom. My cock was diamond hard. Rachel was quick to notice. "I love this cock," she said.

"He loves you, too," was my answer.

I gave her the butter to coat my shaft. She first took it into her mouth, balls-deep! She gave it a few strokes then proceeded to applying the butter to it.

I knelt behind her and had my last taste of her ass before it lost its cherry. Then I started rubbing butter on her puckered opening. I slipped my finger in, working the butter into her rectum. I greased her rectum liberally and used two fingers to finger-fuck her virgin asshole. I took my time working my fingers around to open her up nicely. I managed to insert three fingers into her and as I swirled them I felt her asshole relax.

Her clit was hard and red with lust. I gave it a little suck that made Rachel jump. Then I knelt behind her, aiming my cock at the last refuge of virginity in her body. I moved her knees further apart and adjusted her position for easy penetration.

"Ready?" I asked.

"Yes," she hissed.

I pulled her ass cheeks open with a hand and aimed my cock with the other and applied pressure to her greased opening. "Push back, lover," I whispered as I continued pushing forward slowly but firmly.

Her opening gave and my head started moving in. Rachel was taking deep audible breaths now. Her hole was very tight but in less than a minute, the head was past her sphincters. We paused. I used the same trick on her clit. It worked again and soon she was pushing back and forth, taking more cock into her stretched asshole. Her ass was much tighter than her pussy. It took about four minutes to get the whole shaft inside her and have my balls kiss her leaky pussy.

I pinched her nipples. She came! Her rectum contracted violently around my shaft. I did not dare move in that deadly grip, wanting to save my orgasm till later. When she finished coming, I pulled her upright and back to me and we shared a deep kiss. She knelt down again and I resumed stroking my cock in and out of her stretched asshole in long strokes.

My eyes happened to roll down to her ass, where I joined her. Her asshole was no longer wrinkled, not a single wrinkle. It was stretched to the limit as my thick shaft skewered her. Her anal mouth hollowed in and out as my cock slid in and out of her. That view made my cock get harder and thicker and I fucked her faster. She fucked back stroke for stroke as we both got closer to orgasm. I was back to pinching her nipples. It did not take a minute before she was losing her breath in preparation for orgasm. In a few seconds, we both were grunting as her ass spasmed around my twitching cock. Wad after hot wad of spunk made its way past her rectum, into the depths of her sucking bowels.