A summer of Saturday nights I will never forget. True story
This happened when I was 13 and my sister Emily was 15. I had been jerking off for about a year. I was a shy and sheltered kid, never did anything at that point with another girl, but was very curious. I knew little about sex.
For a couple of years in our house, every Saturday was "date night"? for our parents who worked long hours at a home-based business. The routine was always the same: they would leave around 6 p.m. for either a movie, dinner or some event with another couple and wouldn't be back until 11 p.m. to midnight. My mom taped a $20 bill to the fridge for us to order a pizza.
My sister and I would watch a movie or play a video game while we ate pizza. We got along well. She, like me, was on the shy side and wasn't allowed to date. She was nice looking, but I never thought of her as sexy.
As she got older, she was allowed to have a friend over on Saturday nights, usually her best friend, Lisa, who was hot, nicely developed and was friendly to me. I had a huge crush on her. When they were together, they did girly things in my sister's room and usually ignored me.
One Saturday night at the beginning of summer our routine changed forever. My parents left, I ordered the pizza while Emily and Lisa listened to music in my Emily's room. I watched TV. The pizza came and I ran up to Emily's room to let them know it had arrived. I burst into her room and was in for the shock of my life.
My sister was lying on the bed with her shorts and panties around one of her ankles, legs spread, her eyes closed while Lisa was working a vibrator into her very hairy pussy. They both freaked when they saw me. My sister quickly pulled up her shorts and screamed, "Get the fuck out!"?
I was like a deer in headlights. I couldn't talk. My sister almost never curses and never yells at me. I was crushed. That's when I recognized the vibrator as one of our mom's. (She has at least two that I once found while snooping.)
"I'm telling Mom you stole her vibrator,"? I retorted, not clearly thinking about what to say.
My sister had a stricken look on her face and again told me to get out. Lisa, on the other hand, seemed to be taking it all in stride and calmly commented, "I know how to fix this,"? while turning to me and pushing me down in a pile of my sister's dirty clothes. She pulled down my shorts and started fumbling with my dick. I was stunned. I wasn't hard at first, but after a few strokes I was rock solid. This was the first time anyone had touched my cock and the first time my sister had seen it since we were little kids.
My head was spinning. I couldn't believe this was happening to me. My sister was staring at Lisa as Lisa stroked my cock and could only say, "Oh my God . . . are you crazy?."?
Finally after a few minutes I started cumming and the girls started giggling. At that point I didn't care. It was an awesome experience. My shirt and Lisa's hand were covered in cum. I laid there exhausted.
Lisa looked proud of her accomplishment, and just said, "Nice dick, kid"? while she wiped the cum off her hand with one of my sister's dirty socks. I really felt grown up at that moment, and frankly, no longer felt embarrassed in letting my sister see my cock.
Emily looked at Lisa in astonishment and asked, "Where the hell did you learn how to do that?"?
Lisa replied that she had been giving her older brother hand jobs for a few months.
They started discussing some very intimate details about masturbation like I wasn't even in the room. Lisa revealed that she and her brother Ted had been masturbating each other for a while.
My sister then told me to pull up my shorts and leave, which I did. I went back downstairs, ate pizza, watched TV, then later went to bed and jacked off to the sweet memories of the evening.
Except for coming down for pizza and soda, the two girls stayed in Emily's room the rest of the night. In the morning I saw Lisa leave and she winked at me. I couldn't stop smiling for the whole day.
During the next week Emily hardly looked at me and said little. The next Saturday night she mostly stayed in her room alone. Late in the evening she came out, sat next to me on the couch and told me firmly that I should never tell anyone what I saw or what happened the previous Saturday (which I didn't until now). I agreed and things quickly seemed to be back to normal.
She then asked me if I jerked off much. She said she was impressed with the size of my dick (It's only about 5 1/2"?). I asked her if she wanted to see it again. Taking no reply as an affirmation, I pulled down my shorts and started fondling and wanking. She watched intently. It didn't take long until I came all over myself. She seemed impressed. We then went our separate ways to bed.
Pretty much the same happened the follow Saturday. The Saturday after that I got bold and told her I needed to see her naked if I was to give a repeat performance. She was very reluctant, but after some prodding, took off her top and showed me her tits. As small as they were, they were the most beautiful things I've seen. After I came, she went to her room, locked the door and I imagine rubbed one off.
The Saturday after that I hit the jackpot. Lisa came over again for a sleepover and brought some beer I think she stole from home. They drank two cans each and were tipsy. (They wouldn't give me any.) They told me to get naked and play with myself. I told them only if they got naked as well. Lisa put on some loud music and did a striptease. She was naked in about two minutes. I couldn't believe my eyes. She had a perfect face AND body. Beautiful blonde wisps of hair on her pussy and perfectly shaped tits. I got naked and started pulling on my cock. Lisa was lying on my sister's bed, spreading her legs, lightly rubbing her pussy and every once in a while would stick her middle finger in her hole. I was in heaven.
I didn't last long, but Lisa was still going at it. Emily must have felt left out because she pulled her shorts and panties off and started quietly masturbating in a chair across the room. I was sitting in another chair, cleaning off my dick with a towel. I was still semi-hard watching Lisa build up to an orgasm of her own. After a few minutes she hopped off the bed came over to me, kissed me and started massaging my cock. In her tipsy state she got down on her knees and put her mouth on my organ. I've never felt anything like it. She had velvet lips. She sucked on me for about three or four minutes when I let go of my second load of the evening. My focus was only interrupted when I heard the quiet groans of my sister. It was a surreal scene. We just sat there for a while and enjoyed the afterglow.
Nothing much happened the next couple of Saturdays, even though I tried to initiate another session with my sister. I think she was embarrassed.
Then one Saturday a few weeks later, Lisa came back with her brother Ted. He was the coolest guy in school, perhaps 16 or 17, tall and good-looking. The three of them were in Emily's room listening to music and just talking. I know they didn't want me around, but I crashed their little party anyway. My sister wasn't allowed to have boys over when my parents weren't home and she knew the secret was safe with me as long as she treated me well.
Anyway, we all hung out in Emily's room and before long we all were in various stages of undress and masturbating. They didn't pay much attention to me. Lisa wanted to show Emily Ted's cock, which she seemed to be proud of. Lisa and Ted masturbated each other, while Emily stared at Ted's cock. It was about 7"? and thick. She got up the courage and awkwardly grabbed it and started stroking. I think it's the first one she ever touched.
It was a great evening. We all had at least one orgasm. As I was getting hard after cumming for the first time, Ted came over to me, pulled my hand away and started jerking me off. The girls giggled.
Then just as I started cumming, he lowered his head to my cock and sucked me for all it was worth. It was incredible. I was spent and didn't know what to say.
That's the only time that happened, but my sister and I did continue to masturbate together now and again. Then after a few months, she turned 16, started dating and our sessions ended. She and Ted even dated for a while and she confided that she lost her virginity to him.
I see Lisa and Ted every once and a while, but we don't talk about what happened. It's like it's no big deal.
Emily, Lisa and I are now in college and I'm sure we all are continuing to expand our sexual horizons.