A few weeks passed since my first lovemaking session with my sister-in-law Mary and my wife seemed to be oblivious to it. Mary and I stole every moment we could to have sex, even quickies, in many parts of the house. It was sometimes difficult considering the size of the townhouse and the fact that my wife and her other sister was constantly with us. Even at that, we managed satisfy each other a good number of times.
I was surprised at how horny Mary was and more surprised at how much she seemed to enjoy having sex with me. To keep up appearances, I also had to have copious amounts of sex with my wife with the hope that keeping her satisfied would keep her mind off observing anything out of the ordinary between Mary and myself. I think it worked as life was blissful and all was happy at my home.
But even with my wife and Mary around, I started to develop thoughts about their youngest sister Anne. Anne was 22, about five foot 4, which made her the tallest of the three sisters. She had nice athletic legs but what really turn me on is her size 34C breasts. She wasn't as eye-catching as my wife but had a certain quality about her that made her desirable to me. Anne was the good girl of the sisters and had just one boyfriend so far who she broke up with for being too aggressive and jealous. As far as I know, the guy never even got to first base. As far as I knew, Anne was still a virgin.
For some reason, she was always open with me. I think she saw me as another big brother and told me a lot of things about what was going on with her. I like our relationship and I really enjoy Anne's outlook on life.
When I first met Anne, she wore dowdy and oversized clothes which hid her breasts. I had always thought she was flat like Mary. However, there was one day we went out to the beach and I finally saw them at their full glory. She wore a nice bikini top and I immediately noticed the size of those things. I had an immediate hard-on which would have been noticed had I not been wearing baggy shorts. Since that day, I've fantasized about sucking those melons. Sometimes, I had a choice of masturbating on thoughts of Mary's ass or Anne's tits.
Well, on another weekend afternoon, little did I know that I would be one of the most important things in Anne's life.
My wife had to go on an errand with Mary which would take them most of the day to do as they had to travel about two hours out of town. I decided to stay home and catch up on some reading while Anne decided to stay home to clean up the house as it was her turn to do that particular chore.
Around mid-afternoon, I decided to stretch my legs and see how Anne was doing and got out of the room. I saw her in the TV room arranging the DVDs as I we had a couple of movie nights and a lot of the discs were just lying around. Anne was wearing tight short shorts and a body hugging top which showed off her magnificent breasts. She wasn't wearing a bra so I could easily see her nipples poking.
"You had anything to eat yet?" she asked.
"Nah, I got caught up reading and forgot it was already late in the afternoon," I replied.
"Want me to fix you something?" she asked.
Feeling a bit hungry, I told her I wouldn't mind a salad or sandwich if it was alright. She said she was also a bit famished so she'd fix us a couple of sandwiches.
As she bent over to get the last of the DVDs, I quickly glanced at her cleavage and saw a flash of her nipples. Again, my mind drifted to sucking those twins. As my thoughts wandered, I failed to notice that Anne caught me looking down her top. She immediately stood up and straightened out her top. Needless to say, I was embarassed and looked away and mumbled something about how hot the day was.
She silently went to the kitched and prepared two BLTs and called me to the table to eat.
We chatted about what was going on and I asked her about her job and how things were going. She mentioned that she was happy with what she was doing and the people at her office were great. I asked if there were any cute guys she could go out with and she replied that there were a couple that looked good. Then the conversation turned a bit hot.
"There's a couple of cute guys but I can feel they just want me for something all men want," she said.
"And what would that be?"
"Well, they look at my tits all the time and it creeps me out. Makes me feel dirty."
Trying to sound brotherly, I told her, "Well, they are very attractive, you know. In fact, those are some of the best boobs I've seen. No disrespect."
She looked at me strangely which told me that she may have been offended by what I said. I immediately apologized and told her I had meant no malice by what I said.
She just smiled and to my surprise, said, "You think so?"
Trying to be blase about it, "Actually, yes. They're nicely proportioned and round just like men want them."
"This conversation is getting a bit weird," she replied.
"I know. I'm sorry," I immediately apologized.
"It's alright, Joe. I know you mean well. We've always been able to talk about these things anyway."
"Yeah, well, let's just forget about it. I don't want you to get creeped out by me," I shyly returned to her.
We continued to chat about other things and finished our lunch. She stood from the table and bent over again to get my plate. As she did so, I again so her cleavage and those nice nipples. Again, she caught me and sat down. She looked at me in a strange sort of way and I felt very guilty and awkward.
"Joe, were you looking down my top?" she asked quietly.
"Yeah. I'm sorry. It's just that your boobs are so gorgeous. I couldn't help myself," I stammered.
She just looked at me for a minute and finally said, "Would you like a better look at them?"
"What?," I said incredously.
"Do you want to see them?" she again asked.
Throwing caution to the wind, nodded my head.
To my great exhiliration, she stood up and slowly took of her top. Out popped the most magnificent breasts I had ever seen. They were still perky and high on her chest as I don't think any man has touched them at all. All I could do was stare and admire them. My cock had immediately hardened and started to poke through my boxers.
"Well?," she asked with an innocent smile that all the more made me want to take her.
"Those...those are just fantastic. Gosh, you'd make a great Playboy centerfold," I answered.
"Would you like to touch them?" she quizzed.
"May I?"
"Go ahead, Joe."
Looking around out of reflex to see if anyone could see, I stretched my hands out and cupped them tenderly. My thumbs worked on her nipples slowly. They were now alive and hard. Taking care not to be too rough, I squeezed her boobs gently and just took stock of them. I couldn't believe I was finally touching those breasts that I had fantasized on for so long.
Looking at Anne's face, her eyes were closed and I could feel she was enjoying it. Her legs were shaking and I could see the beginnings of moisture forming on her white shorts. She was moaning softly while I was kneading her breasts over and over.
She opened her eyes and looked down and saw my now rock-hard cock totally out of my boxers.
Smiling, she asked if she could touch it. I told her to kneel and stroke it. She did so and slowly took a hold of my cock and stroked it.
"Believe it or not, this is the first time I've ever held a man's...uh...thing," she said coyly.
"You're shitting me," I said.
"No. I've never let anyone touch me this way and I've never touched a man in this way either. I'm saving myself for the right man."
With self-control, I slowly pushed back and took her hands off my cock gently and said, "Look Anne, I don't want you to regret doing this. I'm your brother-in-law and I know you'll meet some other man who can give you what I can't give."
She looked at me with those innocent eyes and simply replied, "Joe, I've always wanted you to be my first lover. I don't know why but I've always been comfortable with you and I know you'd never hurt me. That's also one of the reasons I agree to move in with you and my sister."
Anne's words slowly sank in me with disbelief. I asked myself what was up with the women in this family? Did all of them want me?
As I gathered myself, I asked, "Anne, I'm really flattered but are you sure this is what you want? This is the only time you'll lose your virginity and I wouldn't want you to regret this as time goes by."
She replied, "Joe, I've never been so sure of anything in my life.
My heart started to pound and my cock was as hard as brick now. "Alright. I'll be gentle. Don't worry."
"I know you will. You'd never do anything to hurt me," she slowly murmured.
With that, I told her to sit on my lap and just let things happen. She sat facing me and I started to kiss her passionately. Her moist lips were soft and as I parted her mouth, I flicked my tongue in and out. She was now breathing hard and I could feel her trembling on my lap. We kissed for a few minutes and embraced passionately. She took of my shirt and started to kiss my nipples. As much as I wanted to enter her, I knew I had to make her first time special and wanted to prolong this as much as I could.
I kissed her again and started to make my way towards those nipples I had dreamed of having in my mouth for such a long time. With the first suck, she let out a gasp of surprise and slowly settled down, enjoying each and every sensation she felt for the first time. She held my head against her breasts while I continued to dart my tongue around both nipples, alternating from one to the other.
This went on for a few minutes until she pulled slowly away and looked at me.
"Joe," she said, "can I put your...uh...thing in my mouth? I've seen it in some porno movies and I want to know how it feels like."
I wanted her to eat me but was a bit worried because her mouth was smaller than Mary's and she may have a hard time getting my cock inside.
"Okay, be careful though. It may be a bit large for your mouth."
She knelt again and stroked my throbbing cock before gently lowering her mouth to take it in. Amazingly, she managed to go halfway and started to suck. I could feel her teeth scraping a bit and told her to just relax. She followed my coaxing ang established a rhythm which felt great. She slowly started to go deeper and with each motion brought me closer to coming.
I guided her hands to massage my balls and willingly did so. There was just something about teaching a first-timer how to pleasure a man which turned me on. She kept on sucking and massaging for a few more minutes. In between, I could hear her groaning while going up and down.
As I felt that I was about to come. I told her to stop and let me do something else which she might enjoy. I told her to stand up again and I slowly unbottoned her shorts. Lowering them, I was taken aback to see that she wasn't wearing panties. Staring at me was a perfectly shaved pussy, just like Mary's. It was a bit reddish and smooth and I could see some of her juice glistening on her inner thighs.
"Lie down on the table," I instructed her.
"What are you going to do, Joe?" she asked surprised.
"Just let it happen," I told her with a reassuring smile.
I stood up from my chair and got a pillow from the couch and helped Anne lie down on the dinner table.
"This feels weird," she giggled.
"Wait till you see what happens next," I winked at her.
I sat down on my chair again and pulled her towards me, her ass and pussy on the edge of the table. I slowly opened her legs and started to lick the sides of her pussy while placing my hands on her stomach. I could feel her stomach muscles trembling, as if her senses were being assailed by unknown forces.
I made my way towards her labia and started licking them like I would an ice cream cone, making sure I was tender. She let out a moan and suddenly grabbed the hair on my head. I continued to work my tongue from the top to the bottom of her slit, all the while tasting the sweetest juice I've ever had. I finally got to her clit and she let out another soft cry. Her pelvis started to rise in pleasure which made me all the more aroused. I played with her clit and could feel more juice building up in her pussy.
While still eating her, I slowly took of my boxers and started to stroke my cock which was now ready to attack. I opened her labia a bit to see if she still had her hymen and could see the thin filmy barrier intact. She was now breathing hard and biting her hand.
As I played with her clit with one finger, I asked her if she was ready for me to penetrate and take her virginity.
"Yes!," she shouted. "Please be gentle, Joe. Please promise me it's not gonna hurt."
"It'll hurt the moment I go in but it gets better after a while," I honestly said.
"Okay," she breathed out. "Take me, Joe. Please take me."
With that, I positioned my dick to enter her and slowly inserted it in her. She was grimacing as I slowly entered and kept mouthing that it was starting to hurt. I asked if she wanted me to go all the way in and she nodded her head.
I decided to burst her hymen in one quick motion to get the pain out of the way as soon as possible. I thrust my whole cock in her and heard her shout in pain which immediately gave way to continous groaning as I went in and out of Anne. There was some blood on the dining table and on the floor which for some reason, excited me. I continued my motion and Anne was now almost unconscious with pleasure but with a smile in her face.
After a few minutes, she said she was felt like she was going to burst from her pussy and I knew she was going to have her first orgasm. I quickened the pace and asked her if she was about to come. When she said yes, I told her to tell me so we could come together. A few more moments and she yelled that she was ready. I gathered myself and said I was ready too. Next thing we knew, we our juices exploded in each other felt a wonderful release. I shot a big wad inside Anne and I felt her juices pouring out onto the dinner table.
I pulled out and went to the kitchen to get some paper towels to wipe off the blood from my cock and from the table top with Anne just lying down and breathing hard, still on the table.
She slowly got up looked at me. Smiled.
"Are you okay?" I checked with her.
"Yes. Just a little sore, but great. Thank you, Joe. Thank you for being my first time," she said. A wisp of hair fell on her face and it was the hottest thing I've seen in a while. Those not-so innocent eyes anymore studying me.
As weird as it would sound, I replied, "Anne, it was my honor. I hope I didn't hurt you too much."
"No. It was just as I thought it would be. I don't thin I could've had a more tender lover for my first time. Now I know why my sister fell for you."
"Speaking of your sister," I said softly, "I hope she never finds out about this, you know."
"Are you kidding me? If she finds out, we'll never be able to do this again."
"Again?" I asked.
"Yes, again," her eyes twinkling. "I want to do this again with you."
"But Anne, you'll find someone who can do this with you regularly without having to sneak around,"...
