My Best Friend’s Older Sister

I had turned 18 back in April. I was like any other red blooded teen male. Horny all the time. Now in June the weather was hot and humid, and women were wearing more revealing clothing in public. I went to the local bookstore and purchased a few, well, magazines. I kept my head down as I stepped out of the store and ran into someone. I dropped the brown bag and the magazines fell out. The stranger bent to put up the bag, but she was no stranger. It was Samantha, my best friend’s older sister. I turned red and couldn’t make eye contact with her.

“My my what do we have here,” she asked smiling as she read the top title. It said 30Something at the top. It’s a magazine with nude women who are all in their thirties. I always had a thing for older women, all because of Samantha. She is fifteen years older than me. Now at thirty-three she was the epitome of a MILF.

“I… I… Sorry,’ I stammered looking at the ground.

“So, you like older women or is it one woman,” she teased.

She dragged a finger down her neck and over her cleavage and down her stomach. She was wearing a yellow floral print summer dress. It was apparent that she wasn’t wearing a bra. Her nipples poked though and were visible through the thin material.

“You sure have grown up, haven’t you Ryan,” she asked rhetorically as she licked her pouty lips.

Samantha grabbed my hand a dragged me around the corner into a small alley. She pushed me against the brick wall and stood on her tip toes to kiss me. I kissed back with passionate awkwardness. My trembling hand reached up and grabbed her breast. She moaned into my mouth. I released her breast and broke the kiss.

“We can’t do this. You’re married and have children,” I said stepping back.

“I am no longer married, and the kids are at their Dad’s house for the weekend,” she said. She grabbed the bulge in the front of my shorts and cooed, “I want you to fuck me with this.”

I pulled her to me and kissed her again. “You are full of youthful energy, but you need to work on your kissing. Follow me to my house and I am going to teach you how to love a lady,” Samantha said letting go of my hand and walking to the sidewalk.

I followed closely behind her. We weren’t parked too far from each other. That made it easier to follow her. We pulled up to her place and she let us in. As soon as the door closed, she turned and pulled her dress off her shoulders, allowing it to fall to the floor. She wasn’t wearing any panties either! She stepped out of the crumpled dress and slowly walked over to me. My eyes were wide and my heart was pounding.

I didn’t want to mess this up. My dreams were coming true. She kissed me softly on the lips as her hands pulled my shirt out of my shorts. Then she grabbed the bottom of the shirt and pulled it up over my head and tossed it on the floor with her dress. She ran her hands over my chest and down my stomach to the top of my shorts. With expertise she unbuttoned and unzipped my shorts, letting them fall to the floor. She kissed me more, wrapping her arms around my shoulders. Her ample breasts mashed against me. I slowly worked my tongue around her mouth this time. Not wanting to slobber all over. She playfully nipped my bottom lip and giggled as she walked away.

Samantha was at the bottom of the stairs before she spoke, “Are you coming?” she held out her hand for me. I took her hand and she led me upstairs. Instead of her bedroom she took us to the bathroom. She turned on the shower and then turned to me. She pulled my boxers off, finally freeing my aching cock.

Her mouth enveloped the head of my cock. “Mmm,” she moaned. She pulled her mouth off my cock with a pop. She grabbed a new disposable razor out of the medicine cabinet along with shaving cream. Samantha then stepped into the shower and pulled me in with her. The water was cooler than I expected. Setting the razor and shaving cream down she grabbed the bar of soap and lathered up her hands. Then she started at my neck and shoulders and washed my body. Her hands soaped up my chest and down to my stomach. She went lower and avoiding my cock. She squatted and washed my legs down to my ankles.

My cock was bouncing inches from her face. I pushed forward a bit hoping she would take me into her mouth again, but she had other ideas. Grabbed the razor and shaving cream she proceeded to lather and shave my pubic hair. Once satisfied that I was hairless and smooth, Samantha stood up and said, “My turn.”

I lathered up my hands and brought them to her neck. She sighed as I massaged down to her shoulders and arms. I reached around and soaped her breasts. Her nipples are bigger than gumdrops and very sensitive. I slid my hand lower sliding over her stomach. Samantha reached her arms back over her head and wrapped them around my neck. I leaned down and kissed her neck and nibbled on her ear.

She gasped as my fingers slid over her hairy pubic mound and found her shaved pussy lips. Her knees went weak as I slid a finger into her eager pussy. Samantha spun and kissed me. I found her slit again. She widened her stance, allowing me better access. This time I slid two fingers in. I couldn’t believe how tight she was considering she had two kids through natural childbirth. As I brought her to her first orgasm she sunk her teeth into my chest. I removed my fingers and finished washing her body, paying more attention to her fine ass.

When we were clean, she turned off the water and stepped out. She grabbed two towels, wrapping one around her waist. She was still dripping wet as she led me to her bedroom. She kissed me and maneuvered so that the bed was to my back. She broke the kiss and pushed me. I fell back onto the bed. Samantha giggled and climbed onto the bed and got between my legs. She kissed the head of my cock. Then she kissed her way down all the way to my freshly shaved balls.

I had a couple girlfriends give me head, but Samantha was by far the best I had ever had. The smoothness of being hairless added to the experience. She kissed her way up my cock again and then took my whole 7 inches down her throat. Her tongue tickled my balls. I moaned as she pulled her lips up the length and then slid my cock all the way in again. She sensed I was getting close to cumming, so she stopped and crawled up next to me.

“Wow! You are amazing,” I said breathlessly. Samantha smiled and kissed me.

I slid down and kissed the side of her neck. She ran her hands through my hair and cooed. Slowly I kissed my way down her breasts and took a nipple into my mouth. Samantha’s legs rose up and she bent her knees and spread them wide. I knew what she wanted so I made my way down between her legs. I kissed her from her stomach all the way down to her inner thigh. Once there I took in the most beautiful sight I had ever seen. Samanth’s pussy was shaved. The only hair she had down there was a strip just above her slit. I could see her juices flowing out, and I could smell her essence.

“Go ahead. She won’t bite,” Samantha teased. I leaned in and ran my tongue up and down her labia. She was so wet. After a few licks I stuck my tongue as far into her honey hole as I could. Samantha moaned and grabbed the back of my head. I slid my tongue up until I found her clit. There I wrapped my lips around it and gave a little sucking pressure. “Ooh… Just… Like… That…,” she cooed. Samantha’s legs closed, clamping my head between them. I lapped her juices and sucked her clit until she orgasmed. “Fuck! So good,” she exclaimed.

Samantha pulled my head up and brought it up to kiss her. “Lay down on your back,” she instructed. I moved from on top of her and laid down next to her. She then straddled my hips and hovered her pussy just above my cock. Lowering herself until her pussy lips were touched my cock. She slid up and down my length, coating my cock in her sweet nectar.

“Mmm… That feels good,” I moaned as I reached up and grabbed her breasts. I pawed at them for a minute.

“Pinch my nipples. I love when a man does that,” she cooed.

Reaching down, Samantha lifted her pussy up and grabbed my cock, guiding it to her slit. She let the head of my cock enter her. I moaned again. My wildest dream was happening. “Ready,” she asked as she slid my entire cock into her eager pussy. I rolled my head back and grabbed her hips. I was in heaven. Samantha started to gyrate her hips. I could feel my cock rub against her cervix.

“Your cock feels sooooo good, Ryan,” Samantha cooed. It was taking every ounce of self-control to not cum in her quickly. Thankfully after a few minutes Samantha lifted off my cock and got on all fours. “Fuck me from behind,” she demanded. I got into position and lined my cock up with her pussy. Then I slid the head of my cock up and down her wet pussy lips. “Shove it in me and fuck me hard!”

I placed my cock against her entrance and grabbed her hips. Then thrust my cock in as hard and as deep as I could. “Fuck,” she moaned. Still holding onto her hips, I started to pick up my pace making sure to slam into her every time. “Yes! Just… Like… That…” Samantha was started to pant. Her pussy tightened and she was slamming back into my thrusts. She had a full body orgasm which made me cum deep in her womb. It was the biggest load I had ever unleashed. When I pulled my cock out cum ran out of her well fucked pussy.

Samantha rolled onto her back and giggled as she scooped up some of the cum with her fingers. She then brought her fingers to her mouth and licked my cum off them. Fuck, that was so hot. “Come here lover,” she said. I crawled up to her and she kissed me, allowing me to taste some of my cum on her lips. When she broke the kiss, I fell onto the bed next to her to catch my breath. Samantha cuddled up to me and threw an arm and leg over me. We fell asleep like that for about two hours. When I woke up Samantha was looking at me. She smiled and gave me a kiss.

“Let’s go take another shower and get cleaned up,” Samantha suggested. I nodded and we got up and walked to the bathroom. She turned on the shower. This time the water was steaming. I grabbed the soap and started to wash her body. We didn’t waste too much time in the shower. Once we were clean and dried off, we went back to her bedroom to get dressed. “I really enjoyed today. I would like to do it again sometime, but I want you to understand that I do not want a relationship,” Samantha explained.

I nodded and said, “I’d like that and I understand.” She gave me a kiss and walked me to my car where she kissed me again with a promise to get in touch with me soon. I drove home in a daze. I had just had sex with my crush. Samantha is a sex goddess, and I couldn’t wait to taste her again.