At the young age of eighteen, my best friend Cathy was embarrassed to still be a virgin. Even more so after I had lost my virginity.
I had lost my virginity several months prior to that to a man that I met during a summer job. His name was Mark, and he was about ten years older than me. (See the Lost Virginity story). Mark never took me out on dates. He would appear at the house on Sunday mornings when he knew my family was at church and take me as he pleased. I was young, naive, and desperately wanted a boyfriend. I was thrilled that he liked me, so I did everything he asked of me. I didn't realize it at the time, but Mark wasn't interested in dating me. All he wanted was sex, lots of sex, and I was easy prey.
He not only took my virginity, but he trained me to be his submissive sex toy. In those few months, I went from knowing nothing about sex to being fully experienced in everything imaginable. I had very low self-esteem and Mark used that to his advantage. I was taught that my role as a girlfriend was to sexually please my man in whatever way he desired. His training started me on a sexually promiscuous path for many years to follow. I had no idea what a real relationship was like.
Cathy and I had been best friends since grade one and were inseparable. We told each other everything. Throughout my ordeal with Mark, I told her every steamy detail. I was on the phone to Cathy the minute Mark walked out the door. I swear we discussed every detail and sexual act at least a hundred times. Cathy was so fixated on my relationship that she admitted to touching herself every night as she thought about what had transpired. Yes, Cathy needed to lose her virginity quickly.
Cathy's virginity and lack of sexual experience became a priority. After many discussions, we eventually came up with a plan. Like me, she developed later in life, but she was now ready to lose her virginity. Being her best friend, I had made up my mind to assist her in whatever way I could. After all, what are best friends for.
Cathy was very cute and outgoing. All the boys loved Cathy. I loved hanging out with Cathy as she was fun and attracted lots of guys. I was always the restrained, quiet one. The fact that I had lost my virginity before Cathy puzzled me.
Back then, we were too young for bars, so our hangout was the local mall. We would hang out there every weekend and flirt with the boys.
We had met a couple of boys, Rob and Mike. Cathy and I both liked Rob as he was the cuter of the two. But since our mission was for Cathy to lose her virginity, I insisted that she could have Rob and I would match up with Mike. I wasn't really crazy about Mike, but this wasn't about me, I had to do my part to make this happen for Cathy.
We discussed Rob for hours. He seemed like the perfect guy for Cathy to lose her virginity to. He was cute, funny, our age, and went to a different school than us, so things would be discreet. It was decided Rob was the one.
My parents were heavily involved in the church. Every Saturday evening, they participated in church events. This meant I had the house to myself. So Cathy and I came up with a plan to meet the guys at the mall, and if things went well, Cathy would give me a signal and we would invite the guys back to the house. The plan was set.
Short denim shorts, braless tops, and high wedge shoes were our standard flimsy attire back then. We spent hours puffing up our hair and applying make-up. We did our best to look hot and sexy before setting out for the mall.
That evening we met the guys at the mall and hung out with them. Cathy was having fun with Rob and seemed to be getting along great with him. Things were going as planned, except she wasn't giving me the signal to go back to the house. I was getting worried that she was chickening out. Time was also running out, as my parents would be returning home in a couple of hours.
Mike was the serious type. We talked about a lot of things, but honestly, there was no spark. He was fixated on my boobs and couldn't take his eyes off of them. My nipples have always been perky, but his constant staring at them made them erect and even more visible through my tight, flimsy top. I had no intention of having sex with Mike, but I did have to keep him interested for Cathy's sake.
Cathy and I made eye contact, and it looked like she was finally ready to take the next step. I suggested that we all head back to my place as my parents were out. The guys seemed surprised but quickly agreed.
We arrived back at the house, and we went directly into the basement TV room. This was my space. My older sister left home years earlier, and my younger sister was seven years younger than me, so I had claimed the basement area as my space. It was nothing fancy, just an old couch, a chair, and a TV, but the best thing was that it gave me privacy from my parents.
The plan was simple. If things were going well with Cathy, I would take Mike upstairs so Cathy could have some privacy and hopefully fulfil our mission...for her to lose her virginity.
I dimmed the lights and we both sat at opposite ends of the couch and began to make out with our guys. Well, the couch barely sat four people, so it was a bit crowded. The guys were at each end of the couch, and Cathy and I were side by side in the middle. We started to make out. I wanted to take it slow with Mike, but he was being very aggressive.
Cathy and I had our backs to each other, and since this day was about Cathy, I wanted to keep track of how she was progressing with Rob. I let myself fall back on the couch so that I could see Cathy. As much as I was trying to fight off Mike he had his hand up my top and was pulling and grabbing at my breasts. I saw Rob sneak a peek at me as he played with Cathy. I have to admit this was a turn on for me.
After a while of kissing and petting, I could see things were getting quite heated with Cathy and Rob. Rob finally had his hand up her top and Cathy was rubbing his groin and chest. I could see Cathy's top being lifted up and her perky little boobs peeking out from under her top. I must admit that watching the two of them made me feel aroused. I had not been with a guy since Mark, and I have to say I was getting quite turned on watching the two of them make out. I was jealous of Cathy, as I would have loved to get my hands on Rob.
It looked like it was time, so I struggled to lift myself off the couch from Mike's grasp and I straighten my top. I took Mike's hand and led him up the stairs to the main floor. He followed me like a little puppy drooling for his reward. Once upstairs I began stalling by going to the washroom and talking. But he soon pulled me down onto the living room couch and we began to make out.
Just then the phone began ringing and ringing. I ignored it, but whoever it was called back again and again. I finally answered the phone. It was Cathy's mom and she had to urgently speak to Cathy. It sounded serious, so I ran downstairs to pass the phone to Cathy.
Cathy was completely topless, lying on the couch with Rob on top of her. Rob had his shirt off, and as he got up, I couldn't help but notice the bulge in his pants. Cathy quickly pulled herself together and took the call. I couldn't help but notice how swollen and red her nipples were as she sat there topless on the phone. All of a sudden, she jumped up, grabbed her top and announced there was a family emergency and she had to go home. She immediately ran up the stairs and out of the house. I was in shock. I looked over at Rob and he was speechless also.
Mike heard the commotion and came downstairs. So there I was standing there in the TV room alone with two horny guys. We just looked at each other in silence.
Damn, now what? I suddenly became nervous being alone in the house with two guys. This was not a good situation. I suggested that maybe they should leave and we could try again some other time when Cathy was available. They didn't want to leave, and suggested they wait and see if Cathy would return. I expressed my doubts that she was returning; besides, my parents would be home soon.
That's when Mike grabbed me and pulled me back onto the couch. He wasn't leaving. I wasn't sure what to do, as he easily overpowered me. So, as I struggled, he picked up where we had left off upstairs.
I wasn't really that interested in Mike, as I had paired off with him so that Cathy could lose her virginity with Rob, but now that plan had fallen apart. I was resisting his advances, hoping to figure out how to get them out of the house. He was right back to fondling my breasts. I thought maybe if I let him feel me up a bit, he would be satisfied and leave. The kissing and fighting went on.
As I struggled with Mike on the couch, I forgot about Rob. As I turned to change my position, I noticed Rob sitting on a chair opposite the couch, watching intently. He was only about six feet away. Him watching me so closely flipped a switch in me. I immediately became aroused. I had never had a guy watch me before. He was just staring at me as Mike was trying to make headway with my boobs.
Our eyes met and locked. He had a look of desire in his eyes. Damn it, he was so cute. I wanted to be making out with him, not Mike. I could see he was trying to catch a glimpse of my boobs as Mike was attempting to lift my top. As Rob watched, I let down my guard and let Mike lift my top, exposing part of my boobs to both him and Rob. I could see Rob's eyes just about pop out as he leaned closer. My breasts were fuller and more developed than Cathy's. It occurred to me that Rob liked what he is seeing. Is he into me? Mike was touching me, but I was fantasizing that it was Rob that was touching me. I could feel myself getting wet as Mike pulled and pinched my nipples.
I wanted Rob so badly now. He was right there in front of me for the taking, but what about Mike? I was very timid at the time, but my desires and lust for Rob overcame my shyness, and I nodded my head to invite him over to the couch. He immediately moved to the couch and sat on the other side of me. Here I was sitting on the couch with two guys alone in the house. What was I thinking?
Rob just sat there and politely watched. As Mike was kissing my breasts, I reached behind and grabbed Rob's hand and moved it to my waist. He got the hint and was soon kissing the back of my neck and fondling my tits. I was fighting Mike off in front of me, but from behind I was letting Rob have his way. I reached back and began rubbing Rob's crotch. I could feel he was good and hard. At first, Mike was too preoccupied with my boobs to notice, but when he did, he didn't seem to mind.
This was the first time two guys had their hands on me. The sensation of having hands all over me was incredible. My boobs were being groped, and my erect nipples were being tugged and sucked. Someone had their hand in between my bare thighs. My pussy was being stimulated through my shorts. I was thoroughly enjoying all the attention now that Rob was involved. Things were heating up fast!
Mike unbuttoned my shorts and began pulling them on. I had to stop this before it got out of hand. It was getting late, and I knew my parents would be home soon. My father catching me having a threesome in the basement would not go over well at all.
