The event that had me lose my virginity happened when I was 14. I never really met the two brothers after that again. I have seen them from a distance, they usually give me a smile and blow kiss and goes away. Between 14 and 18 years of age I have had sex only a few times. Most of the time I usually prefer to pleasure myself with whatever I can find thats shaped like a penis. I even once made a cock with plaster of paris, but it was heavy and felt like harsh rock rubbing inside my vagina. The reason I prefer to have sex with my dildoes are probably my reluctancy to deal with the hassle that comes with doing it with a real person.

When I am on my own, I can fuck myself as long as I want and however I want. I really liked anal after the brothers made it enjoyable in my asshole. I would spend time after school in my room fingering my asshole and dildoing it relentlessly. I used moisturizers as lube, which kind of felt like cum. It was really an enjoyable experience.

The first time I had my hands on a real silicon dildo was when my best friend gave me her's since she got a new one. I cant say my best friend's name here so I will call here Rita for now.

Rita was my best friend since 7 th grade. We always shared our secrets and fantasies with each other. She came from an upper middle class family. She was just as tall as me but had a well developed breasts and a cute bubble butt. While I was a skinny one. She had a porcelain skin and a lighter complexion. She sported a short hairstyle. Her face was ovalshaped with pointy chin. Her big black eyes were always a noticable feature.

This happened when I was 16. I was in 9th grade. Rita once invited me over to her house for a sleepover since her parents were away for the weekends. I arrived at her house at a Saturday evening. We had ordered some pizza and was watching romcoms. Once it was around 8 at night, we went to her room. I casually asked her about her older dildo that she promised to give me. She laughed out loud and said I am too horny and need to calm down. Then joked maybe we could try it tonight. She then went under her bed and pushed out a big box. Once I opened it, I saw it was filled with her plushies and other childhood toys. Rita reached into the bottom of the pile and pulled out a faded blue colored dildo and held it towards me smiling. "Thats yours!" She said.

I slowly grabbed it by my hand and examined it closely as I never had something like that before. The dildo definitely had been put to good use by Rita, the color has been faded. It had a good length of 6 to 7 inches and a very good girth. It had two balls at the bottom which could be used as a handle.

Rita then pulled out another new red one from the bottom of the pile and held it on her face and smiled. It was a deep red color and was as big as her face. It even had the the vein texture on the side. I asked her how she got her hands on it without her parents knowing. She replied she made an Amazon account and brought it as cash on delivery with the money she saved. She timed her delivery date when her parents wasnt in the house.

Rita slowly started putting it in her mouth as she looked at me and once it was halfway in she pulled out with a gag noise and laughed. I challenged her I could deep throat it till the balls hit my chin. Rita luaghed at first but accepted the challenge. She then gave her didlo to me. I took it and spat on it, then rubbed my spit all around the dildo. Lubing it up with my spit, I held it over my head and tilted my head above opening my jaw wide open. I slowly inserted the tip then slowly pushed it down. Once I felt the tip on back of my throat I almost had a gag reflex, but I relaxed my breath and closed my eyes. I was making some weird gag noises and it felt like it took forever. All of a sudden I felt the balls touch my chin and my eyes opened in excitement, pulling the cock out from my mouth. A good amount of my saliva followed out with the dildo and I gasped for a big breath of air.

Rita was in amazement, she clapped her hands and laughed. she then called me a good whore and pat my head like I was a good dog. Rita then took the dildo from my hand and started inserting it in her mouth. Since it was pre lubed from my throat it kind of felt easy for her. Halfway through I could see her struggling and her eyes filled with tears. She eventually gave up and gagged out the dildo. She was gasping for air with her gaping mouth drooling with saliva dripping to the floor.

I laughed as I declared I was the winner. She smacked me with the wet drooling dildo playfully as we both laughed out loud. I was excited at the moment and asked her if she ever put the didlo in her ass. Rita made a surprised disgusting face and said no and she laughed. I had to explain how good it felt and convinced her eventually sharing my experiences with anal play. Rita got excited and told me we should watch some videos. She turned her computer on and we searched for some good anal videos that we could enjoy. We started with one where the girl was with her dildo and told the viewers how to do it and get it into the asshole. I looked at my friend as she looked at me the same time. It felt weird watching it with her, even though we have talked about similar things before. We eventually came across another video where two girls dildoed each other in the ass.

I casually said maybe we should do that as I laughed. Rita's right hand was on the mouse and the left hand was slowly gowing down inside her shorts. I looked at her and she scoffed at me saying if I have never done this before. I slowly started fingering myself as well. Since it was just the two of us I took my t-shirt and panties off to get more comfortable on the floor. Rita looked down at me and said I was such a whore for doing that while Rita was sitting on her chair But I didnt give a fuck as I was so turned on and I couldn't wait to try the dildo she gave me.

I grabbed the dildo and slowly started inserting it in my vagina, I saw Rita looking at me in amazement as she slowly stopped fingering herself. She got down from that chair and was on all four on the fuzzy rug where we both were on. I kept my legs as wide apart as I fucked myself with the dildo. Rita was watching me as she slowly sat on her knees, she looked at me scanning my entire body like a hungry wolf as she had drooled from her mouth. She then remarked that I looked hot.

Rita slowly took her clothes off and started feeling my body with her hands. Her hands ran across my belly, breasts and face, eventually she brought her face closer to mine and gently place her lips along mine as we kissed. I had to stop my dildo halfway as I was indulged in her kiss.

I have neither been with a girl in a sexual act nor ever thought it was attractive, but at that moment I enjoyed every touch. Her hands were soft and so was her body. Rita stopped kissing and lifted her head looking into my eyes. We looked deep into each other and then went back to passionately kissing. I dropped the dildo and started touching her back and then her meaty breasts. Rita was a good kisser, she kissed my lips, nose, eyes, forehead and eventually going around my ears and neck. It was very different from what I experienced with men. Everything felt very warm, gentle and passionate. Rita was laying on top of me as I grabbed her butt while kissing simultaneously.

At some point in between kissing and cuddling, Rita got up and turned towards my vagina and placed her vagina near my face. It was basically 69 but she was on top of me. Rita played with my clit with her tongue. My head was filled with ecstasy. I ate her pussy like I hadnt ate anything in a while. I could feel her wet pussy and asshole dripping onto my face.

After a while Rita told me we should move up to the bed as it was getting a bit uncomfortable on the floor. We relocated to the bed. While Rita was sitting on the bed looking all cute with her pale breasts hanging. I took the dildo and told her to be in doggy position as I started fingering and licking her butthole. After few minutes I covered the dildo in lotion and slowly screwed it into her asshole. It was slow and I could hear her breath from her mouth. Eventually I would take the dildo out and try to stretch her anus with my hands. At some point I was able to fit the whole dildo in her asshole. I can hear the fast paced heavy breathing from Rita. I asked her if she liked the feeling. She nodded biting her lips. Then I slowly pulled it almost out and inserted it back again. Going back and forth with the dildo I could hear Rita's moans and feel her shaky legs. Rita climaxed sooner than I thought and I slowly pulled out the dildo leaving a very large gape. Her butthole was quenching and I could hear it. All the lotion we used were pushed out of her gaping wet anus. She had a droopy mouth and smiled looking at me. She layed on the bed as she breathed. I slowly crawled on all four to her and started kissing again.

I kissed her bosom and fondled it. Rita pulled me closer and kissed me abruptly. She whispered she had the greatest time tonight and continued kissing.

Rita then grabbed the dildo and told me now it was my turn as she giggled. I layed back keeping my legs open in an 'M' position . As Rita started working on my anus I said I wanted to try both dildos at the same time. Rita was surprised and scoffed at me saying I was trying to out- slut her. I took the blue dildo, grabbed it with my both hands. By Lifting my legs slowly I started penetrating myself in my vagina. Rita simultaneously started fitting her dildo in my anus. I was able to get my asshole open pretty quick as it was something I did at home regularly during my pleasure sessions. The feeling of two dildos working simultaneously on both my holes reminded me of the time when the 2 men double penetrated me when I was 14. It was almost like I was trying to relive that moment, I fucked myself hard with my dildo while I told Rita to do it faster. After few tries I was able to climax and leaked some piss on to Ritas face.

Rita immediately wiped it away and layed back on my side as we both breathed heavily. Rita placed her hand on me and started laughing, I joined in on the laughter staring on to the glowing stars on her ceiling. Rita exclaimed it was the wildest day of her life and we both laughed. We cuddled together with gentle kisses and fell asleep eventually.