Here’s a new storyline. Sorry to those folks asking for the continuing of other story lines. I have to go where my creativity takes me. Hopefully if you liked the others, you’ll enjoy this one. Mind you, this is a bit different than my others. There is far more exposition and it takes quite some time to get to the ‘action’ as it were. And, while definitely fantastical, it is not near as over the top. And now the typical disclaimer about how this isn’t meant to be realistic, so no need to post messages about “That would never happen, blah blah blah”. And lastly, thanks for all of the support from folks who enjoy my work. Your comments and emails are what keep me going!
Josie, Sister – Josie Davis
Esther, Roommate – Esther Baxter
Denise, Roommate – Denise Milani
I was a bundle of nerves as I stepped off the plane at La Guardia airport. Here I was; 18, just out of high school, and a Midwest farm boy, and I was soon to be in New York City! On top of all of that, I was going to be living with my sister whom I hadn’t seen in three years.
Josie was the oldest of the five of us, with me being the youngest. Seven years my senior. She was also the black sheep of the family. Why? Not for getting into trouble, being a bad student, being an alcoholic or any of the other things that usually upsets parents. No, she had graduated with honors, and had a six figure job. But that job was in New York. That was the problem. Unlike my other siblings who are still living near Iowa city with the rest of the family, Josie went out into the world and didn’t look back. When she did come to visit for holidays, my family would make all kinds of snide comments. It finally came to a head a few Christmases back, and Josie finally had enough. A fight ensued and she vowed never to return.
Unlike the rest of my family, however, it never bothered me that she left. I mean, I missed her…a lot, but I was proud of her. Even when we were younger and she would talk about ‘getting out of this place’, I was always supportive. I knew she wanted bigger things. She deserved better things!
Despite the age gap, Josie and I had always been close. When I was very young she was protective and tried to guide me. As I got older our relationship grew. She’d help me with homework. I’d listen as she talked about friends/boyfriends/school. And when I started getting interested in girls, she gave me lots of advice and confidence. Which I’m not too modest to admit helped me get quite a few objects of affection.
And when she cut herself off from the family three years ago, she and I kept in touch as much as we could. Tons of email and regular phone calls. We had a very open and frank relationship. We could talk about anything. Including when I started having sex my senior year, she was graphically descriptive with advice to improve my skills. And, it worked. I gained quite a reputation from the girls around school. I also have to admit that it put some really…shall we say ‘interesting’ mental images into my head regarding my sister and her advice. See, Josie is probably the first girl I noticed in a sexual way. And her openness about sex only made it harder not to think of her in that way. Those long legs, tight ass, firm breasts…
Anyway! I had long ago secretly decided to follow in my sister’s footsteps. The big city sounded amazing. And thanks to the encouragement and help of my sister, not only did my grades merit being accepted into NYU, but they included scholarships that would make my education nearly free (of course, being a State track champion didn’t hurt). Which was great news, since my parents were going to pretty much disown me if I left. And if that didn’t do it, the fact that my sister not only offered up staying at my place, but insisted, certainly would.
And here I was. Crowded city airport far from my old home; a place I would likely never be welcome again. But that was alright. The second I came out of the terminal, I was greeted by the beautiful voice of my sister, calling my name seconds before I was caught up in a big hug. I received a big kiss on the cheek before she pulled away and held me at arms length. She looked me up and down, as I had done quite a big of growing in the last three years. While she took me in, I did the same to her. The long legs I mentioned earlier stood atop two inch heels, bringing her nearly to my 5’11” height. A business-like skirt ended just above her knees. A powder blue sleeveless sweater hugged her waist and chest, with the collar of a golf shirt poking out the top. Shoulder length blond hair framed her face and a pair of glasses perched on her nose were windows for the soft blue eyes that scanned my figure. This all happened very quickly before Josie spoke.
“Brian! You look great! And it’s so wonderful to see you!” She exclaimed and hugged me again. I caught myself noticing the smell of her hair.
“I look great? What about you? You’re amazing!” I said back. It was true. She was turning out to be one of those women that got better with age. She had been great at 22 and had somehow managed to get better.
“Flatterer.” She said as she broke the hug again. She had a sly grin that told me that she knew damn well how good she looked. But at the same time she was happy that I thought so.
We got my other bags and hopped in a cab, which I should point out was my first cab ride. As we headed towards Manhattan, I gaped open mouthed while looking out the window. Josie pointed out various points of interest. Even so late at night, the city was so alive. I knew I was being a total yokel, and I could see my sister’s bemused smile reflected in the glass as she watched me. When we finally pulled up to her building, we were greeted at the door by an actual door man!
“Good evening, Miss Stevens.” The well groomed man said, as he held the door open for us. “Can I help you or your gentleman friend with the bags?”
“We’re good Arnold.” She smiled back at him. “And this is Brian. You’ll be seeing a lot of him in the future.” He gave me a look which seemed to say ‘You lucky dog’. I found it odd that she didn’t introduce me as her brother.
While we rode the elevator up, Josie readied me for her roommates. “Now, remember, Esther and Denise can be a bit…gregarious. And they certainly aren’t modest. So don’t get all embarrassed or shocked by what they say or do. And you’ll have a hard time offending them so don’t get uptight. Just be yourself. They’ll fall in love with you in no time.” She smiled sweetly.
“Got it, sis.” I replied, steeling myself for my first meeting with Josie’s two best friends. I had heard much about them, but never actually met them so I didn’t know what to expect. With what Josie had told me the options ranged from between them answering the door naked to greeting me with a kick to the groin.
We exited the elevator, dragged my bags to her door and she unlocked it. From the couch bounced two figures of loveliness. And when I say bounced, I mean it. They both possessed the kind of bodies that even after the main body had stopped, other parts continued to jiggle and sway.
I knew the dark caramel creature was Esther. She wore pajama shorts and a lacy bra that hugged her wide hips and full breasts wonderfully. She gave me a sultry look from her almond eyes. Denise was originally from eastern Europe. She smiled a dimpled smile, like some girl next door. But it was hard to focus on the smile with the enormous pair of boobs threatening to rip through her over-stretched t-shirt. Even though I knew who was who by Josie’s descriptions, she introduced us anyway.
“Girl,” Esther exclaimed “You did NOT tell us your brother was such a hottie.” I felt my face flush.
“Oh, so cute. He’s blushing.” Denise commented, her voice containing a hint of accent.
I dropped my bags and nervously extended my hand, to shake theirs.
“Oh, I don’t think so.” Esther said indignantly before pushing my arm aside and enveloping me in a hug. Her big tits squished against me and I felt a stirring in my jeans. When she pulled away, Denise immediately took her place. Her larger bust changed my ‘stirring’ into ‘full speed ahead to erection’.
“Thanks for staying in to meet him, girls.” Josie said to her friends.
“There was no way we were going to miss it.” Denise beamed.
“As much as you talk about him, we kinda had to. Besides, you’re gonna pay us back by letting us take this hunk out on the town tomorrow night.” Esther laughed. I blushed again. And then all three were giggling at my reaction. Thankfully my sister came to the rescue.
“I think, ladies, that my little bro has had a long day. A full morning of our family giving him hell and a long flight. I think he needs a full night’s rest before he can handle the two of you.” This was met with a chorus of ‘boos’. Josie just waved them off and pushed me and the bags towards a room.
“Goodnight, studly.” Esther called after us.
The room turned out to be my sister’s. It was huge, which was saying something for a place in the city. I plopped my bags in a corner and started looking for a blanket. Finding one, I began making a bed for myself on the floor.
“You’re kidding, right?” My sister snapped.
I peer up, over the bed at her. She was changing into her sleep attire. Her blue top replaced by a small baby tee that ended just below her apple sized breasts. She was shimmying out of her skirt, revealing white cotton panties. Now, modesty isn’t something you can afford in a family of 7 people, but the sight before me caught my breath in my throat. And it refused to come when I realized that Josie wasn’t going to be putting anything on over her panties. I have no idea how long I stared before my voice came back.
“Um…sorry. I can take the couch. I just didn’t want to be in any one’s way in the morning.” Josie gave me an exasperated sigh.
“No, silly. I have a king sized bed. More than enough room for the two of us.” With that she plopped down onto the bed and patted the side next to hers.
‘What the heck’ I thought. It’s not like anything was going to happen. I would just have to be sure not to poke her with my morning wood, and everything should be fine. Feeling exhaustion creeping up, I quickly peeled my clothes down to my boxers. When I turned to shut off the light, I noticed my sister staring at me. She looked at me intensely, before shaking her head slightly and then smiling broadly. ‘What was that about?’ I wondered.
I crawled into bed and faced my sister. In the low light I could see her blue eyes gazing at me, a soft smile on her lips.
“Brian, I’m so glad you’re actually here.” She finally said, bringing a hand up to caress my cheek.
“Me too, sis. I’ve really missed you.” her smile widened.
“I missed you too.” She said softly. Then she moved toward me. I expected a kiss on the forehead or cheek. To my surprise she kissed me on the lips. It was soft, but lingered far longer than a simple peck. When she broke, she simply said “Sleep tight.” closed her eyes and sighed.
That little kiss…a kiss that couldn’t have lasted much more than a few seconds, kept me up on and off all night. I knew that I was reading too much into it. I mean, not only was she my sister, but she was an older woman…and way out of my league. And why was I even considering whether she was in my league!? I know I have always had a crush on Josie. And honestly, more than once had thoughts of her come up when I was masturbating, but I knew it was wrong…wasn’t it?
I woke up on and off all night thanks to a combination of sleeping in a new place and the presence of my sister next to me. I could hear her breathing softly as she slept. A couple of times I lifted up enough to look at her face. That same smile was on her lips. She looked so content. Sometime in the early morning I think I finally drifted off to real sleep.
When I woke again, the sun was up. Josie was softly calling my name and gently rubbing my chest. I opened my eyes and saw she was dressed in business attire, sitting next to me on the bed.
“Sorry to wake you, Brian. I just wanted to make sure you remembered that we all have work today. So you’ll have the house to yourself. Keys are on the counter and Arnold will help you with whatever you need.” She whispered and then bent to kiss me on the cheek. I made note that it was only on the cheek…and that I was disappointed about it. And she bent lower and whispered in my ear. “And kudos on your tent making skills. Very impressive.” Then she giggled and left.
Still half asleep I pondered what she meant until I realized I was sporting my usual morning erection. I felt like I should feel embarrassed, but part of my brain was convinced that she hadn’t been kidding about being impressed.
Now that I was awake, I got up and used the bathroom, willing my erection to go away. Assuming that everyone was at work , I stumbled out to make myself breakfast. It never occurred to me that people might leave for work at different times. When I stepped from my room, seconds later Denise stepped from the bathroom she and Esther shared. She had a towel wrapped around her hair, and nothing else. Her enormous breasts, looking so much bigger because of her tiny frame, swayed hypnotically before they disappeared into her room.
“Need help picking your jaw off the floor, sugar?” I heard a voice ask. Esther was coming from the kitchen, dressed for work. Josie had told me that Esther was a teacher. I could now see that she was the kind of teacher that none of the male students heard one word she said, since all their blood spent the entire class in their crotches. On a normal woman it wouldn’t have been so bad, but her full hips, gorgeous ass, and plump breasts pushed her outfit out in all the right places. And, even though she hadn’t been wearing glasses the night before, she was now. It completed that whole “naughty teacher” look. I could only guess that she enjoyed teasing her students like she seemed to enjoy teasing me right now.
She had her books and bag gathered, obviously heading toward the door. As she passed, she glanced down at my crotch, and smiled slyly.
“Your sister wasn’t exaggerating.” she said in a husky voice, and slinked out the door. Dammit! The combination of a naked Denise and Esther’s sexy, hip swaying walk had put me at full attention again.
My brain started working , and I made my way to make breakfast. About ten minutes later I heard the sound of a door slamming. “I’ll see you tonight, Brian!” called Denise. And then the front door slammed. And I was alone.
I spent the day mostly vegging out. The girls had a gym, so a spent an hour on the elliptical, but for the most part I watched TV. Josie had about a hundred times as many channels as back home. And some of them were the racy kind. Which, combined with my run in’s in the morning had me stroking one out in no time. Actually, it wasn’t one. Over the day I did it four times. It got me to thinking that staying here was going to give me carpel tunnel syndrome.
Since she was a teacher, Esther was the first one home. She greeted me warmly before leaving to change into something more casual and then returning to keep me company. We chatted about this and that, nothing too deep. I noticed that, while still flirtatious, she wasn’t anywhere near as intense as she had been this morning.
Denise came home about an hour later and joined us. Where Esther was blunt and saucy, Denise was bubbly. She laughed easily and often. The two of them were definitely making me feel more at ease. And their combined flirting was giving my ego a big boost! And they kept it light enough to keep me from going all shy on them. I mean, I’m not usually shy around girls my age. Josie had long ago given me confidence in that area. But these were highly attractive, more experienced, city women. After a while, the ladies told me to get changed, since they were taking me out on the town.
I was of course, dressed first. Denise later emerged wearing a pair of painted on low rider jeans and a white top that resembled a fancy tube top, or maybe a corset. It started just below her nipples and ended just above her sexy little navel, showing off the disparity of her tiny waist and her enormous chest. She had cleavage for days. She posed for me for a second as I gave a long whistle, as she flashed me her dimpled smile.
Esther came out shortly after. Her top looked like someone had mixed a button down shirt and a bra. It had see through sleeves, and buttons down the middle (which were all undone). At the bottom is scooped under and supported her big boobs, and ended leaving a large portion of exposed flesh before you came her her barely there skirt. She spun for me, causing the skirt to fling out a bit and show off her black thong. Denise giggled as my eyes bugged out.
Not long after we were all ready, Josie returned home. First to leave for work, last to get home. That was just like her. But that’s also probably why she was doing as well as she was. She looked really stressed as she came in the door and plopped on the couch.
“Josie,” Esther started, seeing my sister’s state. “Don’t you be like that. We’re going out tonight, remember?”
“I don’t think I would be much fun. We had a really bad screw up that I had to fix, and I’m definitely not in a good mood.” I could hear the edge in her voice.
“Oh, poop!” Denise cried. Even her curses were cute.
“Don’t worry D, she’s going. She’s smart enough not to leave us alone all night with her handsome little bro.” Esther grinned. Josie glared at her. Clearly not in the mood for games.
“Ladies. I think I might be able to solve this to every one’s satisfaction.” I declared, as an idea came to me. As I mentioned, Josie gave me lots of advice on women. And I took them to heart Some of the advice I just picked up from hearing her complain about her various boyfriend’s short comings.
I got up and sat on the back of the couch, behind my sister, swinging my legs in either side of her. She tilted her head back and looked up at me quizzically as I grinned down at her. Then I gently pushed her head forward and took hold of her shoulders and started working. You see, I long ago picked up that women dig massages. So I checked out some books from the library and practiced on any girl that would let me. And I had a lot of practice.
Josie’s back and neck were all knotted and tight. Under my ministrations however, it only took a few minutes before a contented moan escaped her lips and she visibly began to relax.
“I have never seen anything calm her down so fast.” Esther said, in awe. “You must have some magic hands!”
“God,” Josie groaned “He sure does.”
“Me next!” Denise laughed, bouncing up and down. I had to focus extra hard on the task at hand or risk drooling on my sisters shoulders.
After a good fifteen minutes of work on her shoulders back and neck, my sister’s sweet smile returned. Mind you, she didn’t say she was done, but her friends noticed and rushed her off to get ready. I think they were only halfway concerned with her getting ready. The other half was them wanting a turn.
Denise went first. I had to alter my pressure as she was a fair bit more delicate than my sister. Not to say my sister was big. But she definitely worked out, and was nicely toned. Denise seemed very soft. Especially the twin orbs I now had an aerial view of. I felt like if I fell forward, I could get lost in her cleavage. She purred the whole time and even eventually started stroking my calf as I worked.
Esther butted in, making sure she got some time. After about ten minutes, she spoke up.
“You know Brian, if your hands work this good on places other than shoulders, you have a free pass to my bedroom, anytime you want.” Denise gasped at her friend.
I’m not sure where it came from, but I think I was building my confidence under the assault of Esther’s rather direct flirtations, so I responded “I’m not sure you could handle it, Esther.” She turned on me immediately, kneeling on the couch in front of me and stared into my eyes intently.
“One night with me, boy” She growled, as she slowly ran her hand up my thigh “And you wouldn’t be able to walk for a week.”
I couldn’t take my eyes off of hers. That is until her hand reached my crotch. Then I jumped and fell off the back of the couch. Both of them burst out in laughter, just as my sister came in. I couldn’t see her from my vantage behind the couch.
“Come on you two. You have all night to mess with my poor little brother. Don’t break him so early.” She joked.
I got up and saw my sister standing there with a big grin. Now, she may not have been dressed as scantily as her friends, I thought she was stunning. A ruffly kind of pink satin button down shirt, hugged her just right. A pair of tight white pants covered her long legs and showed off her toned behind. She finished it off with three inch open toed heels. And she had apparently put in her contacts. She extended her hand towards me.
“So little brother, you ready to hit the town with three of New York’s finest?” She said, posing as her friends took up positions on either side. I stood there speechless for a minute before finally nodding vigorously. They all laughed as they swarmed me and dragged me out into the big city.
It was too early for the club, so we started with dinner at a nice uptown restaurant. Good food, great wine (they didn’t card and my sister insisted), and amazing company. Each of the ladies I was with were intelligent, interesting, and funny. And let’s not forget; Damn Sexy.
After a long wonderful dinner, we slowly made our way to the girls’ club of choice. Chosen not only because it was one of their favorites, but because they knew they could manipulate the doormen to let me in.
The club was trendy, and while not full had plenty of people in it. As soon at the music hit them, Denise and Esther started moving to the beat, swaying so wonderfully. We found a booth and the ladies ordered drinks. I wasn’t much of a drinker. Plus I wanted to keep a cool head. The ladies were all very touchy feely. Even my normally calm and collected sister. And not just with me…with each other. Which in some ways was even more stimulating.
Eventually the girls wanted to move to the dance floor, and one of my weak points was revealed. I didn’t know how. Well, I could slow dance. I had done that at prom, but regular dancing wasn’t something I ever had the chance to learn. This fact in no way deterred my entourage. In fact, it simply spurred them on. I was pretty adamant about not making a fool of myself. But Josie had a plan.
“It’s simple. You dance, facing me, and I’ll help you get the hang of it. Denise and Esther will flank you and make you look good until you know what you’re doing.” I had to admit, it would probably work. With those two gyrating around, no one would even know I was there. I admitted defeat and they dragged me out to the floor.
Josie tried to show me some stuff, but I moved awkwardly. Stiff and nervous. Not to mention, I had Esther and Denise’s butts, breasts, and hands touching me quite often. But it was really watching my sister swivel her agile waist and hips that had me the most unfocused. After a few songs like this, my sister took charge. She stopped my horrible dancing and stepped in close, our eyes just inches apart. I’ve always thought my sister’s eyes were beautiful. The looks she gave were captivating. And the intensity she had right now practically burned my eyes.
“Brian. You need to be confident.” She said, just loud enough for me to hear. “And you have every reason to be.” Then she put her hand on my chest. “Handsome, charming, and sexy. You have three of the hottest women in this club at your beck and call. And you could go home with practically any woman here. So show them all that you are the stud that I know you are!”
And I believed it. I knew that what she just told me was true. At the very least she believed it to be true. And just like that, a switch was thrown inside of me. I started dancing again. My movements loosened up and I began to get into a groove. And before I knew it, I was dancing.
Now, sure, I was far from being a master. But I looked decent enough. And once I got into it, the girls began to really dance with me. I took turns with each one, bumping and grinding. I had a blast. And I knew I was the envy of every guy in that place.
I don’t know how long we had danced, well over an hour, but we sure worked up sweat. Eventually the girls wanted more drinks, and we went to find a booth as Denise headed to the ladies room. She tried to get at least one of the girls to go with her (like women do), but they both grabbed one of my arms and said there was no way they were leaving me alone with one of the other. So Denise made a pouty face and walked off.
Drinks flowed, with me partaking in some, but not near as much as the others. Josie and Esther were extra flirtatious with me, talking about how sexy I was out on the floor. Esther bluntly admitted that I had made her ‘horny as hell’. Denise eventually emerged from the ladies room, but was intercepted on the way back by some guy near our table. It was quickly apparent that Denise had no desire to talk to the guy, but he had her blocked. He was lucky it wasn’t Esther he was dealing with. I was betting she would have just kneed him in the groin instead of trying to politely get away. I sprang from the table when he started getting handsy with her. I could see her light up as I came over and tried to rescue her.
“Hey, buddy.” I said, gently grabbing Denise and pulling her to my side. “This lovely lady is with me.” He made a face and looked over at our table.
“Looks like you already got your hands full.” he grumbled, motioning to my table a few feet a way.
“First off,” I said, stepping up to him. “I’ve been keeping all three of these visions more than happy, all night long.” Denise molded into me and put her hand on my chest.
“He sure has.” she said with a grin.
“And second, this sensual beauty is far more than a guy like you could ever handle.” Denise just grinned at him.
I could tell he wanted to hit me, but wasn’t sure how that would turn out. Track has kept he in really good shape. He backed down and grumbled “whatever” as he walked away.
Denise turned to me and shouted “My hero!” and then threw her arms around me and kissed me deeply. And it was not a casual or friendly kiss. Full blown, passionate, tongue filled kiss! She broke when Esther called out “Quit hogging our man!” She pulled away and flashed me that brilliant smile and led my stunned form back to the booth. My sister gave me a sly lopsided grin, that told me that not only was she not mad, she seemed a bit proud. Like a ‘go get `em, tiger’ look.
“Your brother is a great kisser!” Denise said as we sat down.
More drinks, lots more flirting, and tons of innuendo. I was constantly playing footsie with someone. They were all very impressed at my white knight showing. Even though I hadn’t drank very much, I was intoxicated. The girls however, were quite drunk on alcohol.
Denise and Esther decided they wanted a bit more dancing before we left. Josie, however, claimed to be too drunk. They turned to me, and I fought them off, saying that I was going to keep Josie company. Rather than fight, they gave each other a look, grinned, and left us alone.
Once gone, Josie snuggled against me. “I was hoping you’d stay. I haven’t had almost any alone time with my favorite guy.” I put my arm around her and hugged her into me, and we just sat there enjoying each other’s presence.
The music changed to something slow and Josie perked up. She pulled me from the table and found a nice out of the way place nearby. She began slowly swaying, her hands around my waist. I put my hands on her hips and moved with her. For the longest time I simply lost myself in those baby blue eyes. The look she gave me was a mix of intensity and adoration. Eventually she pulled herself closer, putting her hands up my back and resting her head on my shoulder.
“You’ve been really amazing tonight, you know that don’t you?” She whispered. Her breath on my neck sent shivers down my spine. I just mumbled something nonsensical.
“And it won’t be long before I lose you to Esther or Denise…or both. I’ve never seen them take to a guy like this.” More shivers.
“You’re not going to lose me to anyone, sis.” I managed to get out. I really wasn’t sure what was going on. I knew right then, in my heart, I would pick Josie over either of her roommates without hesitation. But I also knew she was very drunk, and probably didn’t realize how she was coming off. Or would even remember this in the morning. But what I said seemed to placate her.
“Hmmmm…I hope that’s true.” She said in a dreamy voice.
The music had long since changed, but we were in our own world. We didn’t stop until I saw Esther and Denise returning. I tapped my sister and she opened her eyes to see her friends approaching. They both had huge grins, but it was obvious they were pretty tired.
“Shall I take my ladies home?” I said, cheesily.
As we left, Josie never let go of my arm. She leaned on me the whole way and as we waited for a cab, way to tired (and in their cases, drunk) to walk back. Not wanting to wait for one of those van sized cabs, we crammed into the back, with Josie on my lap in the middle. Surrounded by so much exquisite female flesh…and my sisters tight tushy bouncing on my lap. Lets just say that I hoped she was drunk enough not to notice the thing poking her rear.
We made it to the building, and stumbled inside. The girls all decided that they wanted to rinse off all of the sweat they had built up. My sister disappeared into her bathroom and I couldn’t help but notice that Denise and Esther went into their bathroom together. I putted around the living room to give Josie some privacy, until I heard noises of pleasure coming from Esther and Denise. My erection from the cab returned. Not wanting to get caught in an awkward situation, I retreated to Josie’s room.
I had just gotten undressed and ready for bed when I heard a moan from Josie’s bathroom. I jumped up, to make sure she was OK. The door was cracked open a few inches so I could peak in. The sight that greeted me showed that she was more than OK. Her bathroom is one of those with a big hot tub-like bath. Currently Josie was sitting up on the edge, leaning against the tiled wall. Her head was thrown back and eyes closed. One hand fondled a very erect nipple topping her firm breast. The other was placed between her long, lithe, and widely spread legs slowly rubbing her tightly trimmed pussy.
I was surprised that I didn’t faint! I was also surprised that my brain wasn’t telling me to quit watching. Instead, I stood there with my dick quickly poking through the fly of my boxers. Minutes went by. Her legs would sometimes quiver when she’d rub herself just right. She continued to moan lightly. At some point, my hand found my cock and began to stroke unconsciously.
As she began to build, she slipped a finger into herself. Shortly after, she inserted another. Her movements sped up. Her moans changed to stifled cries as she pumped faster and faster. My own hand went on auto pilot and matched her. I couldn’t believe this was happening. With everything that had happened tonight, and now being capped by the most erotic sight I had ever laid eyes on. The way she arched her back and swiveled her hips. The tone of her pleasure sounds went right to my aching cock. I knew that this was my sister, and it was wrong. But I couldn’t help it.
She finally reached her peak, and managed to shock me even further. As her orgasm raced through her, causing her hips to buck, she cried out “Ooooooh, Briiiiiaaaan!” As she came down, my own impending release approached. She slowly opened her eyes and looked right into mine. She smiled wickedly, and I realized I had been caught, my hand immediately leaving my erection. But instead of freaking out, she just looked at me and mouthed the word ‘cum’. And I did. Without even touching myself, my cock exploded, shooting my considerable load all over the door.
When the last shot fired, Josie got out of the tub and grabbed a towel. She moved toward my frozen form. Opening the door, she slowly wiped my cum from the door, tossed it towards the hamper (missing), and stumbled to the bed. Plopping down naked and face first.
At this point, blood returned to my brain and started making sense of things. I remembered that the girls were VERY drunk. Josie leaning on me at the end of the night may have been because she could barely walk. She probably wouldn’t remember any of this. I gently slid into bed and she turned toward me with a warm smile. But her expression showed that she was half gone already. I laid on my back and tried to let her pass out and let myself try and ignore the fact that she was naked. She quickly went out, but not before scooting against me and laying her head on my chest. And with that, she was gone with a contented sigh.
I must have laid there for a couple of hours, not able to shut my brain off so I could sleep even though my body was exhausted. Thoughts of what I had done. What I had seen. What did it mean that she called out my name? Had she known I was there? What would she do when she woke up sober and realized she was in bed with me naked? I tried (and failed) to stop thinking about how she looked…her angelic form. In my memories she almost glowed. And I felt horrible for thinking that her soft cheek and warm breath on my bare chest was the most heavenly feeling I had even experienced.
My brain finally burned itself out and sleep enveloped me. I slept like the dead. No dreams, waking up, or anything. When I finally woke, the sun was up, and I was alone. My brain immediately worried about how my sister had responded when she woke. To prolong the confrontation I took a long shower and dressed. Cautiously emerging into the living room, I found the three roommates chatting away at the breakfast bar. They stopped when they noticed me, each grinning like a Cheshire cat. Denise and Esther were still in their pajamas, which is to say mostly naked. Josie had on a pair of shorts and a simple but form fitting t-shirt and cute little tennis shoes.
“So, the one that drinks the least takes the longest to recover.” Esther teased.
“Who knew our man was such a lightweight?” Denise laughed in her cute little accent. I blushed shyly, but didn’t speak. I felt like if I spoke, last night would suddenly be brought up.
Josie got up and brought me a McDonald’s bag. “McGriddles. Your Favorite if I remember correctly.” He smile was sweet and certainly didn’t show any hint signs of being upset. “Come on. I want to take you to Central Park. You can eat on the way.”
Now I was worried. Was she putting on an act till she could get me alone? If so, she was a dang good actress. I briefly thought about coming up with an excuse not to go, until I realized that I was already obediently following her out the door like a puppy dog. Denise and Esther called out to us as we left, saying goodbye.
Under the pretense of eating, I delayed any conversation. Which Josie seemed fine with. She simply took my arm in hers and enjoyed the morning air. The walk to the park was short, and soon we were enveloped by the green. It was like we were teleported out of the city. My sister took me a grassy spot in the shade far enough away from the main paths for privacy, but not so far that you can’t see people going by.
“I come here often. To people watch.” She mused. Her voice still sounded normal. No hint of anger.
“Yeah, I love people watching too.” I responded lamely. I could only be mute for so long. Minutes passed as we watched people walk, bike, and roller blade by.
“So, you’re not going to bring it up, are you?” She asked, without taking her eyes from the passers by. The way she asked was still light. No upset tones.
“Um…bring what up?” I asked, playing dumb. Maybe she just meant about whether I enjoyed the night out with the girls.
“Hmmmm…maybe the part where you peaked in on me masturbating? Or the part where I caught you beating off while you watched me? Or the part where you crawled into bed with your naked sister?” She finally turned to look at me and she had a big grin.
Suddenly, a light came on in my head. When she said ‘caught’. I thought the same word when she opened her eyes after her orgasm. I had originally thought I had been caught, as in ‘red handed’. Now I was thinking that maybe I had been caught, as in a trap! Now facts were sliding into place. As realization spread to my face, she laughed lightly.
“Wait a second! Why was the bathroom door cracked open in the first place? And why were you sitting on the edge and not down in the water? Did you say my name just to mess with me?”
“Oh, now I’m on trial?” She said, jokingly. She was still perfectly calm. “Well, let’s see. The door was cracked because I knew that after how worked up you got my roomies, they would definitely be joining in on some activities that would make you nervous and drive you back into our bedroom. Heck, I would have joined them, if you weren’t here-”
“Wait? You’re gay? THAT’S why you haven’t had a boyfriend in a few years?” I interrupted.
“No.” She smiled. “I’m just open to enjoying life from any angle. And I haven’t had a boyfriend because I have been waiting for mister right to come around.”
“But let’s save that conversation for later. I was answering your other questions. So, I left the door open knowing you would eventually be in our room and hoping you would get curious.” My eyes widened, which caused her smile to grow. “I was on the edge of the tub because you wouldn’t be able to SEE anything if was in the water. And I said your name because I was thinking of you when I got off.” She finished matter-of-factly.
I was stunned. All kinds of thoughts raced through my head.
“And before you start thinking it,” She chided “Everything that happened before we got home was genuine. The only reason you didn’t end up in either Esther or Denise’s bed is because I asked them to hold off. You pretty much, literally, charmed the pants off of all of us.”
I blushed deeply, so she reached out and took my hand it hers. I felt tingles up my arm as she stroked it softly. She didn’t say anything for a while, letting things sink in.
“So, uh, you wanted me to, um, watch you?” I asked lamely.
“MMmmmm, more than just watch.” She purred. I felt my pulse rate double. “Last night was just testing the waters, so to speak.” The back of my brain was freaking the fuck out! But the gentleness in her voice and way she held my hand reassuringly kept me calm.
“More? Like what?” I croaked.
Without hesitating, she leaned in and kissed me. Unlike my first night, it was a much fuller kiss. Those soft lips pressed mine and worked gently against me. Without needed to think it, I kissed her back, returning the same gentleness. Her lips parted and I felt her tongue slowly snake into my mouth. It found mine and we began to softly duel.
I followed her lead as our soothing, lingering kiss continued. I was having a hard time holding back. There were rivers of passion I was barely containing. But for some reason, I felt like she was too. Perhaps it was a hint of labored breathing. Perhaps the occasional more aggressive tongue movement. Either way, she was using this to answer my question, so she was in the lead.
After a blissful eternity, she broke our kiss. As she pulled back, I opened my eyes for the first time. Hers were still closed. She took a deep breath and a contented look washed across her face. She finally opened her eyes and gazed at me, glittering as they seemed to moisten. I felt as though she were holding back tears.
“Does that answer your question?” She said, her voice having a slight tremble. I nodded slowly as I took it in. The night before she had shown me her sexual side…a side she obviously wanted to share with me. Just now she had shown me her loving side. Specifically how much she loved me. Not just as a brother, but as a man.
And I looked at her now…she was trembling slightly. Always so confident, I realized that she had just put herself out on a limb. She had bared herself to me and now I had the power to quiet her fears or level her. But the latter wasn’t even a possibility. For so long I had looked up to her, respected her, admired her, cherished her. And now I knew that I loved her. Feelings I had pushed down into a little ball, as I tried to ignore them out of guilt…and the thought of rejection if I ever made them known…feelings now bubbling to the surface. Feelings she obviously had as well and put herself on the line, even under fear of losing someone she cared so much about.
I reached out and gently pulled her against my chest. She took several quick gasping breaths and shuddered against me as I broke the tension. She had obviously been on the brink of tears. I caressed her softly, suddenly feeling confident and strong as I comforted my normally so in control sister. Control she allowed herself to lose as she trickled tears of joy onto my chest.
We must have sat like that for fifteen minutes before she sat up, wiped her tears and put her glasses back on. And then, she was Josie again. Ready to rule the world. She stood, pulled me up, and we walked hand in hand from the park.
We must have strolled through the city for hours, mostly quiet and simply enjoying each other’s presence, before Josie pulled me into a quaint little eatery for lunch. We chatted casually while we waited for our food. I felt like I would burst with happiness. Like a light switch, Josie was right back to herself. At large and in charge. And I realized I was myself too. Not the awkward guy I had been since I got here. So much of that shyness was worry and wonder about how things would be with this woman. Now that I knew, I was on top of the world.
I should also mention that we didn’t just chat. We were constantly holding hands, and Josie regularly rubbed her gorgeous legs against mine. I think she knew how much her legs had always turned me on, and enjoyed teasing me.
After the food arrived, I decided to re-engage a long standing tradition between us: The ability to talk about anything.
“So, whose tits do you like better? Esther’s or Denise’s?” I grinned.
“Denise’s tits are firmer and bigger. But Esther’s nipples are better.” She answered without missing a beat. She looked at me as to say ‘Is that all you got?’ Then she fired back. “Whom would you like to fuck more?”
“You.” I said before she had even finished. She turned the slightest pink. I had tripped her up! But she regained her composure immediately.
“Don’t you worry. You won’t be getting much sleep tonight, sweetie.” She laughed.
“But seriously,” I started after I quit chuckling “How did things start with you three?”
“Well, you know I met Esther in one of my classes. It really did just start out as a friendship. And then we roomed together. And then, after I had a really horrible date, I decided to get drunk and feel sorry for myself. Esther started out comforting me, telling me how stupid men were, ‘blah blah blah’. But as I got drunker, she slowly got bolder. Next thing I knew, we were making out. And when I woke up hung over the next morning, I was naked in bed with her. I realized that not only was I not freaked out, I really enjoyed it.”
“As for Denise, Esther and I met her at a club. She had been watching us all night, said that were were really hot, and bluntly asked to go home with us. Now, could YOU say no two those basketballs?”
“I’m pretty sure I would kill someone if ‘They’ asked me, too.” I grinned. Josie laughed loudly.
“I know, right? Anyway, the three of us definitely made some noise that night. I didn’t expect anything to come of it. Kinda like a one night stand. But a few days later, Denise asked me out to lunch and we got along great. The three of us have been as thick as thieves ever since.”
“So, do you still like guys?”
“I like you, don’t I? But, yes I still find guys attractive. I just think that most of them are idiots. And it’s not like I go trolling for girls. I think Esther, Denise and I just have a special connection.”
I tried to stifle a laugh as a thought came to me.
“What’s so funny?”
“I was just imagining the look on mom’s face if I called and told her all of the evil things the ‘big city’ has made you do.”
“Oh! You should totally call her and tell her what a den of debauchery this place is. And that your big sister is leading you down the dark side. She’d have a heart attack!”
After lunch, we took in some sights and hit a movie. I really enjoyed the latter. Having my sister snuggling up to me the whole time felt wonderful. The whole day felt like a date. It was weird, in that this was a person I already knew better than I knew anyone. But at the same time, it was like a first date. After the movie, we went to dinner. Lots of flirting and innuendo. And eventually heading home. I had to point out to her that it only took two days for me to already see this place as home.
When we reached the door, she went to open it, and I stopped her. She turned back to me and looked at me confused. I quickly but gently took her face in my hands and kissed her deeply. Not the soft slow kiss we had shared earlier. This was kiss was hot and heavy. Our lips mashed against each other firmly, our tongues swirled and probed. Every now and then Josie would moan or growl in her throat, as her breathing began to quicken.
After several minutes, she pulled my hands from her face and pulled in closer, throwing her arms behind my back. My hands went to her hips but rather quickly I decided to be bold and let one hand drift to her amazing ass. I cupped it, feeling its wonderful firmness. She moaned deeply and jammed her tongue down my throat in response.
My sister’s breathing became labored and her hands alternated between raking my back and runner her fingers into my hair. We were pressed so tightly together that I could feel the twin bullets of her nipples poking my chest. After a few more minutes, Josie forcefully broke our embrace. She stared at me with a burning look as she caught her breath. Then she grabbed my hand and quickly pulled me into the house, moving straight to our room. As I dragged behind, I noticed Esther and Denise looking at us with huge grins. I waggled my eyebrows at them, which started them hooting and whistling.
Once inside, Josie slammed the door behind us, and quickly began removing her clothes. I don’t know if she was just so out of patience she didn’t want to bother something slower, or if you knew that I generally preferred to get right to business. Either way, she was naked in no time flat. I had been disrobing myself, left only with my pants, when she finished. Seeing her naked up close and not peeking through a few inches of bathroom door froze me in my tracks. Her perfect skin, firm breasts, thick nipples pointing at me, and nicely trimmed pubic hair leading to her pussy had me in awe.
“Hey.” She said, snapping me from my thoughts. “Enough ogling. I want to see if what I saw last night is really as impressive as I drunkenly remember.”
I knew I had no need to be modest in this area. While I’m not the biggest guy ever, I am definitely well above average. Hadn’t been with a girl yet who wasn’t impressed. I grabbed the waistband of my pants and boxers and pulled the both down in one fell swoop. Her smile widened.
“Ohhhh, I remembered correctly.” She cooed as she stepped up to me. She grabbed my dick in one hand and threw her other arm around my neck and kissed me passionately while she gently rubbed my cock. As we kissed, I moved her backward to the bed, gently laying her down when we reached it.
I changed from kissing her mouth and moved to her neck, sometimes kissing or licking gently at her ear. She moaned and panted as I kissed her, her fingers entwining with my hair and softly clawing my back. Of of my hand began caressing her fabulous leg, working slowly to her inner thigh.
I moved my mouth lower, slowly kissing and licking my way to her breasts. Finding one generous nipple, I rolled her rock hard bud between my lips, alternating between sucking and licking and occasionally a light bite. Her moans continued to increase in intensity, peaking when my hand found the moist lips of her sex. I gently rubbed it, sometimes inserting a finger and briefly probing, other times stimulating her engorged clit.
Suddenly she pulled me up, looking at me with need. “I need you in me. Now…please!” She begged. Not one to let a woman in need down, I moved up as she spread he legs. I lined up my throbbing manhood, teasing her a bit by rubbing the swollen head against her pussy. She moved her hips, trying to capture me in her opening. deciding I had teased her enough, I pushed forward enveloping myself in the burning folds of her pussy. Before I was halfway in, I felt her pussy grip me tightly as her back arched off the bed. She cried out; her hand clutching at the sheets.
I needn’t have waited for a signal to continue. As soon as she recovered, she threw her legs around me, and pulled me down for a sloppy kiss. I knew then that she didn’t want any more slow and gentle. I plunged the rest of my length into her depths causing her to grunt. I pulled out then quickly thrust forward with Josie’s hips meeting my thrust. As we repeated this, my sister continued to cry out and moan. I loved that she was a loud lover. It spurred me on.
I kept going, in and out. Her heels bouncing on my ass. She moaned and groaned beneath me gripping the sheets tightly and calling out “Oh God, Brian! So good!”. She was pretty damn good herself. The velvety contractions covering my cock we quickly bringing me to the edge. It certainly didn’t help that this was my sister and I was more turned on than I had never been. I was actually surprised I had lasted this long. But, considering that Josie seemed to be heading towards her second big ‘O’, I certainly didn’t feel bad.
I did my best to hold off, wanting to cum at the same time as she did. And the time arrived. Her legs gripped me tightly as she wailed “Ooooooh! Briiiiiiaaaaan! Fuck me!” And that was it. I unloaded into her, pumping shot after shot deep within her. She grabbed me with her arms and pulled me flat against her as we both finished cumming. She shivered under me, her breath uneven as I grunted the last of my juice into her.
We lay there a few minutes, just catching our breaths. That’s when I heard clapping from the living room. Josie must have heard it too, as we both laughed exhaustedly. I pushed myself up and looked down into her eyes. They shone at me intently. After a few moments we simultaneously whispered “I love you” and then laughed again. I kissed her softly on the lips, and then rolled onto my back before pulling her against me.
“I can’t imagine how things could be any better.” I mused as I lay there, stroking her hair.. She chuckled.
“Sweetheart, much like out new life together, tonight has only just begun.” She whispered into my ear. I felt a stirring down below and realized that she was most certainly right.