Long time lurker, first time poster. This story happened 2 years back when I was interning in Boston during college. I have two younger step sisters who were in high school at that time. I am three years elder to my elder step sister. So, when she was starting senior year I was starting my junior year in college. This happened during the summer before the junior year.
Although my dad’s family lived in Boston, I hardly visited them during my internship. I was staying with a bunch of college friends who were also interning. As a result I only went to visit him mostly during weekends or at random times. I still had the keys to the house and my own room though. I didn’t have much association with my step sisters as we didn’t grow up together. I am not a jerk and thankfully they aren’t either. So, even though we weren’t close like siblings, we weren’t in any bad terms.
My dad was doing well for himself after he divorced my mom and he had a big house. I haven’t seen much of my step sisters, let alone their friends. One Friday night I went home some what late around midnight. I was having a dinner date that didn’t go as I expected it to go and I didn’t want to travel all the way back to the house I rented. So, I went to my dad’s house and slept. I woke up around 2 AM and went to the downstairs kitchen to get some water. As I was heading I bumped into a girl who was so surprised to see me. I apologized and told her who I was.
We talked briefly for a couple of minutes. She was my sister’s friend and having a sleepover. Thats when I realized, I was in my boxer briefs and she was wearing fleece shorts and tank top. I some how had an erection and it was quite apparent. I grinned as I realized that she noticed. “You’re very beautiful Anu,” I said. “You’re handsome Greg”, she cleared her throat and excused herself to the downstairs bedroom. I couldn’t help but take in fully what was on display in front of me. Her firm tight butt was making all the right moves as she walked. As we finally reached the landing, she said “Good night, Greg” and disappeared.
I have seen her around a few more times over the next few weeks. One weekend I was visiting my dad again. I usually took a dip in the pool if the weather was good. It was really great that Saturday and I was relaxing in the pool. My sister and her friend joined me. Anu looked stunning in her pink two piece. Without making it too obvious given that my step sister was also there I checked Anu out. She was very fit like most girls her age. Her tits were medium sized and she had an amazing ass. I greeted them good morning and they greeted back. They applied oil for a few minutes and slowly made their way into the water. We all hung out and talked about school and weather. “I really like your bikini, Anu,” I said to her when I got a chance. She blushed wildly.
Over the next few visits it was apparent that she took some interest in me and she knew that I was into her. I talked to her while watching TV a couple of times to learn more about her. Her parents were strict immigrants and her dad was a prof. I moved closer to her. “Anu… I’ve thought you were attractive for some time. You’ve blossomed into a stunning young woman. I could never say anything… you’re my sister’s friend. And you’re young. But that night I could barely stop myself from fucking you right there in the kitchen,” I said, still staring at her with a delicious fervor.
“I…thank you,” she replied awkwardly. She was searching for the right words. “I was happy to run into you that night. I’d been thinking about you for quite some time,” she stated. “You have?” I asked, a large, devilish grin spreading across my face. “Well, then I guess we’re both in luck. We have the house to ourselves the whole night.” She hesitated a bit. I asked her what was troubling her. “I….I’m a virgin,” she muttered. I assured her I will take care of it and gave her my number before my sister returned.
She texted me and I texted back. We flirted a little. I asked her if she ever touched herself. She admitted to touching herself that night we bumped into each other. I went out and returned for dinner. After dinner I retired into my bedroom and the plan was for us to meet after everyone is asleep. I told her to text me when she can. She texted me after 11 PM. She kept her door open and I sneaked in. As the door closed, I pulled her closer against my chest. “I am afraid,” she said. “We will go slow,” I assured.
Slipping my hands down to her waist, I pulled her into me with some force. I pinned her against the wall and leaned into her. I took the back of her head in my hand and kissed her on her lips. The tip of my tongue slipped into her mouth as her hands tried weakly to push me away. I wanted her. One hand slid up the front of her waist band and I untied her shorts. She kissed me back. She wrapped one leg around me and pulled me into her. I turned upwards as I pushed her shorts to her ankles and my fingers slipped down into her pussy. She was already wet.
“Wow you’re so wet!” my breath was hot on her face as she blushed.
“No Greg I can’t, this isn’t right please! Be a gentleman…”
“Anu, I am a gentleman! I’ll go slow… inch by inch…”
Grabbing her face with my hands, I landed another kiss on her big, pouty lips. My hands slid behind her legs and I lifted them up, dropping her on her back on the bed. Pulling her thighs to my shoulders, in one move I closed the distance again. Her shorts were already on the floor exposing her pussy, legs in the air. My hands found the fabric of her tank top and this time her tits fell free. My hands squeezed them, finger and thumb working her nipples. I slipped out of my boxers.
“Ohh baby you are soaking wet! I’m gonna slide in so easily!”
“Oh my god Greg no don’t… I’ve never…”
But the shaking in her voice and the soft moan escaping her lips as my fingers toyed with her nipples were pretty unconvincing.
In one smooth move, I reached down to her panties and pulled them to the side. She looked down my body, powerless as I lined my thick, purple cock head with her tiny pussy.
She didn’t know what to expect, but I took her wrists in one hand and maneuvered my cock with the other. I touched her pussy again, my thumb rubbing small circles on her clit making her squirm. Twisting my wrist I slid a finger in her curling it up in a come-here motion. I then replaced my finger with something much bigger. She watched as my head pushed against her lips, spreading them. I made slow thrusts as I entered it fully in. She moaned and gasped.
“Owwwweeeee!” she screamed, stifling a sob as I entered her. I pulled back and pushed again.
“Nice, popped your cherry! Ugh you feel so good babe!”
I was fucking her slowly, rhythmically. I aske dher how she felt and she told me it was slightly painful but she liked it. Stepping up, I fell on top of her driving myself against her cervix.
I slipped her arms around my neck as I took her, pounding away and nuzzling her neck. She felt a sharp pain on her neck as she realized that I was leaving a hickey on her. Marking her.
She couldn’t help but wrap her legs around me as her thighs bucked against my thrusts.
“Ughhh I’m gonna cum baby…” I moaned in her ear.
“Uh.. uh.. uh… Greg… ” she didn’t make it in time before she felt me slow down and spasm. My cock pulsed a few times before she felt the heat and wetness of my cum fill her up.
“Greg… NO! …” Again, she couldn’t finish her thought before she felt a tingly heat rise from her pussy through her whole body.
“Oh my… god… ahhhhh!” she screamed as her body convulsed and mind went blank. She just came for the first time.
As my seed leaked out of her, she wrapped her arms around herself, rolling onto her side.
But after a few minutes, my hands were on her again and I was lifting her up, this time pulling her on top of me. She was on my lap with her tits in his face. Tugging one of my legs around him so that I was straddling his waist he kissed me again holding my head against his face. Pulling my hips downward, I felt his cock already hard again pressing against my pussy.
If I slid in easy last time… this time was even more effortless. It hurt her a little less, but I started trying to buck her off of me, jockeying her as she moaned and held on.
Hand on the back of her neck keeping control, her hands were on my shoulders. My mouth caught one of her nipples and after a few minutes I started to cum again. Recognizing it this time, she tried to push herself off but I leaned back and pulled her into me, sighing with pleasure as I spurted another load inside her innocent pussy.
She threw her head back and let another orgasm take her away. We both were panting as I slipped her off of me and onto the bed.
“Whew… well now that we got that out of the way, now we can go steady!” I told her.
Source: reddit.com/r/gonewildstories/comments/8mg4w5/mf_my_sisters_conservative_friend