All of you have these amazing stories. I suck at English so bare with me.
I’m a late bloomer and didn’t grow muscles or facial hair until college. Because of that, didn’t date much in HS and only lost my virginity to a pity fuck on grad night. I am 2 years older than my youngest sister and she and I are close. I’m the middle child, but it’s not important for the story. I love and protect her. She is my wing woman and is trying to look out for dating material for me while I try and keep the unwanted guy attention off her. When she was a Senior in HS, she was having to decline guys left and right it was so frequent.
She had a few friends that come over often and the taller dark haired one (I’ll call her Hope) started talking with me more one day. I didn’t think anything of it, didn’t think of it as flirting because she was my sisters friend. AKA off limits. Looking back, it was obvious she was sneaking out to come talk to me in the kitchen or chat with me in the hallway outside my bedroom, etc. Hope even started talking about her dating and frustrating sex life. Thought that was odd at the time, why talk to me about about that stuff. She asked what I was into and not even thinking about it, I apparently said the right thing, “Well, I’d be into someone like you if I was to choose.” Eventually, one of the other friends blatantly told me when Hope wasn’t around that she liked me. Then it all clicked. My sister wasn’t thrilled at the idea but didn’t say no either. From that point on, we flirted constantly behind my sister’s back or would sneak out to kiss on the side yard.
We didn’t date, go out or do anything other than when the opportunity presented itself when she was over visiting my sister. This went on for several months and was just a fun adventurous thing we had. Never more than first base.
That would eventually change one day when my Sister and her friends are going out on a shopping date and our Parents are working the weekend (per usual, family business). I am home, just finished some yardwork, preparing to go to work myself later that afternoon when Hope arrives at our door. I answer very puzzled but I didn’t inquire yet. Just let her in and gave her something to drink. I made a statement that was more of a confusing question than an inquiry because I truly didn’t know her intentions at that point. “I take you are aren’t her to wait for my sister…” She just shook her head shyly, looking at the table while both her hands clutched the bottled water. “…are you here to see me?”
The pause and ever so slight smile she made told me everything I needed to know. Everything clicked and I figured it out. I cracked a few jokes and made her feel at ease until I invited her back to my room. She got up and followed me back while giggling softly to herself. I won’t bore you with the awkward details because Hope and I were awkward but horny as fuck. Once we got past the stage of groping and heaving petting, Hope got up and stripped out of multi-layered top. Her bra was hiding a pair of C breasts that were cute and perky. Firm in my grip yet soft enough to melt in my palms. She left her shorts on for now but she helped me get out of my shirt and shorts. I laid back on my bed naked and received a blowjob. Hope was good at it if inexperienced. No complaints from me as I enjoyed the moment. Thankfully I showered afternoon.
After a few minutes, I got her up and wanted to return the favor. I stripped her of her remaining clothes and down came the shorts. She was wearing lacy black panties that left nothing to the imagination to what her ass looked like. I commented that I approved wholeheartedly and she flushed with embarrassment. Panties now removed, she had a trimmed patch of bush and an athletic golden brown skin that matched her ethnicity. Hope laid back and put her knees up and feet scrunched up near her ass. My tongue tasted her and she yelped in surprise and pleaded with me to continue gently. My arms pinned her body down as my face buried into her pussy. Hope moaned and tried to cover her pleasure with her hand and then my pillow.
Soon she was squirming and wriggling with pleasure. She begged me to fuck her. I slid on a condom and Hope changed positions to doggy style. She buried her face into my pillow again and presented her brown skinned ass to me for the taking. I slid my cock into her pussy and it was tight. It took a few tries but I got my girth in. We fucked for 10 minutes while she was on her hands and knees until she couldn’t take that position any longer. Moved to missionary, then over the side of the bed, spooning. Finally she got on top and that is where Hope finally came hard.
Hope got dressed, went home and skyped my sister she was feeling better and able to meet up for round two if they wanted to still go shopping later. My sister never found out about that encounter.
We did end up dating after she graduated HS a few months later but we broke it off when she left the state for college.
Source: reddit.com/r/gonewildstories/comments/hje2qv/mf_my_sisters_friend_ditched_shopping_day_to_come