At age 25 I wasn't ready to settle down yet as I was still having too much fun with the singles scene. I found that I had a particular talent for finding ladies who were also just looking for fun. As a result, I was having sex regularly, at least a couple of times a week, and with many different partners.
Usually only the kinky ladies came for a second night. My two favorites were the gals who would sit on my face while I ate out both of their sweet holes. But even better was the thrill of my balls slapping against her pussy while I fucked her up the asshole. I knew she was really into it when her ass came up to meet me stroke for stroke. I didn't understand the guys who were having trouble getting laid.
I knew that I wasn't particularly special in either looks or personality. I don't mean that there was anything wrong with me just nothing special. I stood right at six feet tall with brown hair, blue eyes and weighed 180 pounds. I always thought that I was good looking enough but no Greek God either. I believe the reason I had success where others didn't was the fact the ladies always knew where they stood and had no problem saying no if they weren't interested which freed me up to approach another gal.
But, the biggest thing was I didn't worry about what a lady looked like. If I saw a lady who looked like she wanted some company I was only too happy to oblige. The old saying of not judging a book by its cover proved true time after time as my best fucks were almost always with ladies who were not beauty queens. The best ever had been with a 350 pound lady who was so sexy and so talented that I didn't keep up with her.
So, as this story begins you can see I was not looking for a new sexual adventure as I thought I was already living out my fantasy life. But, I guess no one has ever really tried out everything absolutely possible sexually. I lived in the thriving city of Kansas City and the Kansas City Royals baseball team was in the 1985 World Series. The other team was ahead three games to two, so one more loss and the Royals would lose. My Sister Naomi had tickets to the next game and asked me to go.
I had a date that night but cancelled it as I might not ever have another chance to see a World Series game. I took off from work early and picked Naomi up and made the short drive down Interstate 70 to the Truman Sports Complex. It was one hell of a game with the Royals scoring the winning run in the last inning. We were both feeling very good and a bit drunk as I drove her home. When we got there she asked me in for coffee and to watch the post game coverage on TV.
As we sat there on her couch I glanced over at her and realized that my big sister had turned into quite a beautiful woman. She was four years older than me but I had never noticed her before as during our teen age years we were both too busy with our own sex lives. Checking her out now didn't exactly arouse me but rather made me proud that she was part of my family. Naomi was 5'7" and weighed roughly 140 pounds with the same brown hair and blue eyes I had. Every bit of her weight was in the right places as she had a huge ass and at least EE breasts. I couldn't help wondering when the last time those big boobs had been titty fucked.
As we sat there she surprised me by showing me tickets to the seventh and deciding game the following night and invited me to join her again. Of course, I accepted in a flash. When the coverage ended I got up to leave and told her good night. As she walked me to the door she stopped me and wrapped her arms around me saying, "Thanks, Adam, for escorting me tonight, I can't think of anyone I would have rather have gone with."
I wrapped my arms around her and felt her twin mounds flatten against my chest and for the first time felt a sexual tingle caused by my sister. I couldn't believe how sexy my own sister's boobs felt against me. But, as if this weren't enough she gave me a little kiss right on the lips as I responded, "No, thank you Sis, I had a wonderful evening with you."
I leaned toward her to give her a peck of a kiss in return. Our lips met again but this time I swore I felt her tongue at my lips as if she were going to give me a passionate kiss. I decided to get out of there before I did something wrong or let my imagination run away with me. Reluctantly we broke our embrace and agreed to meet the same time the next night.
As I drove away I kept thinking about that kiss and the more I thought about it I was convinced that I did feel her tongue at my lips. Just then I noticed her shoes were on the floor in front of her seat. I knew she had plenty of pairs of shoes but this gave me an excuse to more closely analyze her disposition and see what kind of feelings were running between us.
Without paying any attention to the other traffic I grabbed the steering wheel and made a squalling U turn right in the middle of a very busy four lane street. Stopping the car I grabbed her shoes and jogged to her door knocking I heard her yell, "Who is it?"
"Come on in, I'm in the kitchen." I turned the knob and walked straight to the kitchen and my jaw nearly hit the floor as the first thing I saw was her ass. She had changed into a sexy short nightie that just covered her rear end. My God, what a sight it was. Had she been one of my one night stands I would have been all over that ass no further questions asked. If I was turned on before it would be nothing compared to how I felt as she turned around to greet me.
Her nightie was white and made of a very thin material so when she faced me I could clearly see the brown of her areola and nipples not to mention get a full appreciation for how massive her boobs were. A huge bulge instantly formed in my pants as I couldn't help but be aroused. Nonchalantly she asked, "To what do I owe the pleasure of your return visit?"
"You left your shoes in the car and I thought you might need them tomorrow, "I replied gulping and gasping for air. I could hardly breath confronted by this lovely sight. As Naomi walked toward me I watched her tits bounce. She reached out her hand and took the shoes and put them on the counter. She didn't stop there as she kept coming closer until we were toe to toe.
I wasn't sure what to do. There was this amazingly sexy woman in a very hot nightie standing directly in front of me with her nipples an inch from my chest. But, there was one major problem she was my sister. Smiling up at me she wrapped her arms around my neck she drew us back into a hug. She smashed her boobs against me and I felt her crotch make contact with the bulge in my pants. She whispered, "Thanks, little brother, for bringing back the shoes."
"It was nothing," was my weak reply. She looked into my eyes and gave me another kiss. This time I left my lips parted slightly but was disappointed when she tried nothing. Maybe I had imagined her tongue earlier. Her hands dropped down my back and I thought I was about to be shown to the door when her lips found mine again. After a couple of seconds there was no doubt as her tongue timidly passed by my lips and found my tongue.
Before I knew what I was doing I was kissing her passionately as I caressed her back. We kissed again and again. With each kiss our hands roamed more aggressively until we were cupping each other's ass cheeks. Then she whispered, "You turn me on, Adam."
"You turn me on, too," I moaned in response. I never wanted someone so much in my life. I kissed down her neck and pushed one of the straps to her nightie off of her shoulder and kissed down her chest in earnest reaching the meat of her breast. I was ecstatic when I made it to her large erect nipple and took it into my mouth. As I sucked on it feelings of guilt seemed to wash over us.
I continued to suckle on Naomi's boob for awhile longer but I could feel my erection begin to wilt and Naomi had released her grip on me. She was just passively standing there. It was as if we both knew we had to stop but didn't want to break the news to the other. Finally I released her boob and stood straight up and told her, "Naomi, we just can't do this as much as I want to."
"I know, little brother, but I bet it would have been good. I guess I'll see you tomorrow for the game." With that she put her strap back in place and walked me to the door. We exchanged loving, yet confused, looks as I walked out.
Needless to say I couldn't get her out of my mind. The more I thought about her the more turned on I became. I couldn't get to sleep that night without jerking off thinking about her. The next day between thinking of my great opportunity to see the seventh game of a World Series and my Sister's luscious body not much work got done. I kept going over things in my mind. The more I did this the less wrong it seemed to make love with my sister; after all, we did love each other.
The taboo lines seemed to make less and less sense. I decided that we were two adults and could make our own decisions regardless of the rest of the world. That night I would play it cool and see what Naomi's conclusions on the subject were. She surely would have to give me a sign of some kind. I picked her up as scheduled and she looked stunning wearing a tight fitting sweater and equally tight fitting pair of blue jeans.
We enjoyed the game immensely as our Royals won 11 to zero. It was a great game to celebrate and we did downing beer after beer. As we drove home everyone was in a great mood waving at strangers honking their horns in joy, and generally whooping it up. We got to her place in time to see the last of the post game coverage. Something was different tonight as Naomi seemed more distant.
I asked her if anything was bothering her and she said that she was fine. I thanked her for the games and gave her a quick hug. Again my cock sprang to life but it was for nothing. Two seconds later I was headed into the cool fall night to my apartment.
Disappointed and yet somehow relieved that Naomi and I hadn't made love I drove along thrilled at our team's feat. I had almost gotten Naomi out of my mind when I looked down and saw those shoes on the floor board again. I was confused had Naomi left them there on purpose or was it just a weird accident. I was not about to take my chances.
At almost the same exact place as the previous night I did the fastest U turn imaginable and raced back to Naomi's place at warp speed. I had no idea what would happen when I got there. I tried to convince myself that I would just hand her the shoes and leave but was hoping for more. It was just then that I realized that I didn't care about the cost I wanted to fuck my Sister if she were willing. Realizing this I knew I would be able to put the guilt completely aside and was hoping she would too.
The scene started out much the same way as the night before as when I knocked she hollered for me to come in. I, again, found her in the kitchen. This time she hadn't changed but I couldn't help it as the bulge formed again in my trousers. Mockingly I said, "Hey, Sissy look what you left in my car again."
She blushed and came over and put the shoes in their place on the counter. I moved closer and wrapped my arms around her being careful to allow things to stay platonic if she wanted it that way and gave her a good strong hug as I said, "Thanks again for two of the most memorable evenings of my life."
She returned the hug in equal zest. For some reason she was blushing slightly as she said, "Adam, you're welcome this has been the best time I've had in a long time."
Then we looked into each other's eyes and saw something different there. My Sister wasn't in those eyes. All I could see was a ravenous woman. She must have seen something similar as suddenly her lips met mine and she shoved her tongue deep into my mouth. The sister who used to torment me as a little kid was now squeezing both of my ass cheeks as she ground her pelvis against me. I was into it and there would be no turning back as I felt all over her ass. I loved the way her jeans cupped her ass so perfectly as I ran my fingers down her ass crack.
Coming up for air she ran her fingertip down my chest. In turn, I put my hands on her boobs cupping them. Suddenly she swirled around and fell into me so that her ass was against my cock. Immediately I reached back around her and again cupped her boobs and began gently squeezing them.
There is no feeling quite like holding a woman's breast through a soft tight fitting sweater. Naomi began humping my cock through all of the layers of clothing and in a sultry whisper said, "I really have to go piss. Why don't you get us each a glass of wine and meet me in the living room on the couch after you take off your shoes and socks."
"Anything you say Naomi," I whispered as I nibbled on her neck. She broke free and hurried to the bathroom. So, I scurried to the refrigerator and got the wine. I had just settled onto the couch with my footwear removed when she came back into the room. I was surprised that she was still fully dressed. I figured she might slip back on that sexy nightie, but was wrong. When she snuggled down beside me I did notice she had put on fresh perfume.
We were soon locked back in passion as our mouths met again and again. We kissed all over one another's necks as she unbuttoned my shirt and I pulled her sweater off over her head. Wasting no time I quickly reached behind her back and unclasped her bra which seemed to melt off of her chest. Gracefully she fell back onto the couch and I gently followed her down. In moments my lips were locked on the most perfect pair of boobs I had ever touched. My mouth went from tit to tit as my hands worked on both boobs simultaneously. Her boobs were so soft yet beautifully firm.
Her hands dug into my head urging me on. Her whole body seemed to be moving under me as I kissed every millimeter of those fabulous orbs. After several minutes I continued to fondle her boobs with my hands but moved my kissing down her belly. I stopped when I reached the top edge of her jeans. I carefully slid off of the couch so that I was kneeling beside it. I reached for her crotch and began gently caressing her cunt and thighs through her jeans. It wasn't long before I felt her hand first on my ass and then on my cock through my pants.
When she reached for the pull on my zipper I reached for hers and we unzipped each other at the same time. Next, I unfastened her pants as she did mine. This caused my loose fitting pants to fall to my knees. As I reached a hand on each side of her pants she lifted her hips high off of the couch and after a bit of struggle I pulled them down and off of her. As soon as the jeans were off of her ass I could smell that sweet odor of womanhood and see those beautiful royal blue panties. She asked, "How do you like my Size eights?"
"Absolutely fantastic," was all I could get out. I rubbed my hands all over her crotch but couldn't take it any longer and reached to pull these off as well. Again Naomi was quick to cooperate and her panties were quickly shed. I was blown away at the sight of her neatly trimmed but very hairy pussy. It was a wondrous forest of kinky brown hair. As I ogled her pussy she proceeded to push my underwear down to my knees.
Gingerly I ran my fingers through her pubis and I could feel the heat rising from her twat; she was on fire. Her hand firmly clasped my prick as she moved onto her side and began stroking my cock. She pulled me closer and rubbed my cock head against her nipples. She would switch boobs every few seconds and it was driving me crazy. Glancing down I saw a drop of pre-cum on my cock.
She saw it too as she took her index finger and wiped it off and smeared a tiny bit on each of her nipples and then sucked her finger into her mouth to clean off the rest. By now, my hand had found her cunt lips and clit and my fingers tenderly played in her steamy honey pot. She smiled up at me and purred, "Adam, if you can carry me back to my bedew can be more comfortable and you can do just about anything you can imagine."
"With an offer like that I bet that I will figure out a way to carry you back there. God, Naomi you are fucking beautiful." I leaned down and gave her another passionate kiss as she put her arms around my neck. I stood up leaning down and with one hard snatch lifted her off of the sofa.
I struggled at first and thought I would drop her. But, she sensed my trouble and helped me to adjust her weight so that she was more balanced in my arms. Excitedly I almost jogged to her bedroom and the queen sized bed that awaited us. Letting her fall to the bed I collapsed right on top of her.
In no time she had rolled us over and had taken top position. This allowed me to get my first full opportunity to play with her mammoth ass. I had never felt anything like it before. She raised herself off of me and was kneeling beside me apparently turning around. Almost giggling she asked, "What do you think of a woman sitting on your face and having you kiss her pussy and asshole?
"I love the idea." I don't think she cared how I answered the question as before I had three words out I was looking straight up her crotch as she was bringing it ever closer to my face. She had perfect aim as her asshole was directly over my hungry waiting mouth. First, her soft rear cheeks touched my face causing me to shudder with delight. I inhaled the special aroma of her bowels and then stuck out my tongue and flicked it the length of her ass crack.
The sensation of her flavors combined with the feeling of her sparse peach fuzz was overpowering. Her ass came to rest fully on my face as my tongue found her little rosebud. I worked feverishly to stick my tongue inside her rectum. This caused her to wiggle her buttocks against my head. Her anus seemed to gradually open like a flower as my tongue made its way further and further inside of her. I could hear moans of joy coming from her.
Then, she shifted her weight slightly and I was confronted by a totally different sensation. She now had her swampy twat in my face. I dove into her like a starving man licking up the juice that had already flowed from her. Finding her nub of a clit I flicked it with my tongue a few times. She pushed herself harder against my face.
This was my cue to take her clit between my lips and suck softly on it as I rapidly flicked it with my tongue. Almost instantly she collapsed on top of me with her cunt grinding furiously in my face. Both of her hands grabbed my cock as she began jacking me off. She moved one hand to my balls as I felt the head of my prick slip into her mouth. The suction she was creating was terrific.
She wasted no time getting all of my eight inches down her throat. I could feel her head bob up and down and it didn't take long before I shot my first load. She was fantastic as not a single drop escaped. My hips bounced up to meet her every suck. We must have looked like a couple of snakes as much wiggling as we were both doing. Suddenly a gush of her cum poured from her cunt and soaked my face and I did my best to lick her clean once again as I exploded another load into her mouth.
She pulled her cunny a few inches away from my face and rested saying nothing for a couple of minutes. Having recovered some of her strength she slid down my body and suddenly made a U turn of her own so that she was looking me in the eyes. All I could see in her eyes was a very hungry look. Scooting into position she wrapped her hand around my rod and aimed it for her pussy and promptly swallowed the entire pole into her cunt. My god, her cunt was fucking hot and tight. Slowly she began to ride up and down on me as she growled, "Oh Fuck Adam you have a great cock. It is mine tonight. Oh god yes I want it every way possible even if you have to miss work tomorrow my sweet little bastard; oh yes, fuck me."