So when I was a Senior, I had this very hot and sexy female cheerleader friend that was also in marching band with me, so needless to say we would hang out a lot. Now it was no secret that I had always liked her, but she had a boyfriend. He was an ass and was always cheating on her behind her back, but somehow she always seemed to find out. Needless to say I hated the guy and always wished she would dump him and find someone who really cared about her, like me. I was always there for her anytime she needed a shoulder to cry on or someone to listen.
Well I went with her shopping one day. She said she wanted to buy some things to try and help her seduce her man back to her. Naturally I tried to talk her out of it, but ended up being supportive in the end. She had confessed to me that while they had been intimate (mostly BJ satisfaction for him with just a little petting action for her), they had never gone all the way, and she was hoping that if she gave him that then he would stay and not mess around with other girls. I smiled at this because it made me realize this guy was a total douche and didn't realize what he had right in front of him.
So we proceeded to the lingerie section so she could try and find some sexy things that would help her in her quest. Normally I am uncomfortable going into the lingerie section but Suzy convinced me she needed my help, "A man's eye" as she put it to see if she was buying the right things. So with a little reluctance I went along with her. She would grab things off the rack, hold them up and ask my opinion. I tried not to stare too much, but she was definitely catching my attention with her choices. I kept wishing I was lucky guy that was going to see these on her perfect, hot, tight little body. So she would take things into the fitting room and try them on to see how they fit. Then she would come out and search for more. There were a couple times where she was bent so low looking at things that I saw the lacy pink thong she had worn that day. This, along with the sexy little numbers she was choosing, was getting me extremely hard. I was convinced that she had seen the bulge in my pants a couple times and had smiled and winked in a flirty way to egg me on.
So she finally decided on a few pieces and we went up to the register so she could pay for them. I couldn’t take my eyes off the items she was going to purchase; several thongs of various patterns and colors, a very sheer and lace teddy, and a cami and thong set (with the thong having a split in the crotch area). The female clerk behind the counter caught me staring and smiled a devilish smile. I blushed bright red and said, "These are for her to wear for her boyfriend". Dumb move because this made the clerk chuckle and ask if I was the lucky boyfriend. Very softly I said no and blushed an even brighter red. Suzy caught this and winked in a flirty manner with me.
So we get out to her car and head back to her place. On the way there is a very awkward silence in the car. We kept glancing back and forth, waiting for the other to say something and break the silence. Finally I got the nerve up and said "You got a lot of great stuff today. It sure got me going just watching you hold it up to yourself. I wish I was the lucky guy that got to see you in it." Suzy smiled. She giggled and then said "It was very fun watching your expression with everything I kept picking up. It looked like you were getting a little excited!" This made me blush and very sheepishly and quietly I said "I was. I had hoped you hadn't noticed". Suzy said "Its okay. I really liked it. It showed me that there are better men out there than the one I have now. Did you sneak a look at what I was wearing today under my skirt?" This made me giggle and I said "Your little lacey pink thong? That got me the most excited!" Suzy laughed and breathed a sigh of relief as she said "Then I would tell you that all these things I bought today, well, I bought them so I could impress you. I realize what I have in front of me and I don’t want to loose that. So what do you say, you up for a little modeling show?" I nodded, with a huge smile on my face!
We pulled up in front of her house and she frowned a bit, her mother was home and she hadn't been expecting that. "Damn! I wanted out first session to be special, just between us," Suzy said. Then she proceeded to tell me how her mother figured out that I was not only a good friend, but was also longing for Suzy in an extremely sexual way. Suzy had confided in her mother that she was starting to feel that way about me too. Being that her mother was single and hadn’t been sexual for sometime I guess she made Suzy promise that the first time Suzy and I got hot and heavy, she wanted to be there to watch so she could pleasure herself as close to the real thing as possible. So Suzy admitted to me she had agreed to that with her mother. And sure enough when we went inside and her mother saw the bag from the store, she got a huge smile on her face. "Is today the day," she asked. Suzy gave her this look that could kill. She said between clenched teeth "I don't want to do that anymore mom". They both looked at each other for a few seconds and I could see that this was not going to end well. So I looked at them both and said "Look, I am a little shy with this, especially it being my first time and all. But I am sure we can all work something out. Suzy, I know you said you wanted this to be special, but I am not sure it can get more special than this." Her mother smiled from ear to ear and even Suzy relaxed and said "Well as long as you're okay with this, I guess I can be too". Then she turned to her mother and said "But when the time comes, the "end results" are for me to take." Her mother smiled and said okay. This did puzzle me a bit and I started to ask Suzy what she meant, but decided against it because it really didn’t matter.
So there we were in the living room, just standing there staring at each other. I was waiting for someone else to make the first move, because I was a bit nervous and didn’t know what to do. Suzy took my had and walked me to the couch where she sat me down, pausing to rub the bulge in my pants that had not gone away. She stood back up and smiled, then back up a bit while taking off her shirt. The bra she was wearing matched the lacey pink thong I already knew she was wearing. Then she slipped her skirt down her waist to her ankles, stepping out of it slowly so I could watch. I could see that she kept herself shaved nice and smoothly. The thong she was wearing was sheer and there was no trace of pubic hair to be seen. She walked back over to me and stood me up, taking my shirt off me and then unsnapping my pants and dropping them and my boxers to the floor, exposing my huge erection. She smiled big when she saw it and immediately grabbed hold and started lightly running her fingernails up and down the shaft, making me feel so good I fell back on the couch. She got down on her knees and started stroking my cock from the tip to the base in long slow strides, getting me harder than I though I could be. As she was stroking my cock she was tickling my balls with her other hand, very lightly and in all the right places, getting me to moan loudly and arch my back in pleasure. There was no way could have prepared myself for what happened next, I was caught completely off guard. Very slowly Suzy pressed her lips to the tip on my throbbing cock, dribbling spit down the shaft to get me wet. Then she slowly parted her lips as she slipped my cock inside her mouth, all the way to the bas of the shaft. This just about made me cum, and I think Suzy could tell this, because she stopped to give me a break.
Then her mother came over, wearing just a thong a bra like Suzy, only hers was black silk. Her mother was just as attractive as Suzy and I was a little overwhelmed with who I should pay more attention to. As if reading my thoughts Suzy said "It doesn't matter which if us you stare at, I understand. My mother is very sexy. And if you want to feel her from the inside too then I want you to. Today is about making you happy, since I have failed as a friend. Just know that this is the first of many times that this kind of thing will take place." I smiled and leaned in and kissed Suzy very deeply and passionately. Suzy stood up right in front of me while her mother got on her knees and started sucking my cock again. I reached up and grabbed Suzy's tits. They were small, but firm, and had the most perfect little nipples. Suzy shrugged out of her bra while I kept caressing her breasts, playfully pinching her nipples, making her smile with excitement. She reached down to slip off her thong, but I stopped her, preferring to do it my self. Before slipping them off I started rubbing her already dripping pussy through the lace thong she was wearing, making her moan and groan with extreme pleasure. Then I slid the thong down her thighs and around her ankles while she pressed her dripping cunt against my face, rubbing my nose and mouth with her sweet juices. I had never licked a pussy before so I hoped and prayed that I did all right. And I guess I had because every time I would slide my tongue between her sweet pussy lips, she would press it hard against my tongue, making me lick her clit with such force that she was arching her back and moaning so loudly it got my cock so hard that I came in her mothers mouth a bit. Suzy's mom stopped, stood up and kissed her daughter, letting my cum spill into Suzy's mouth so she could really taste me. Then she looked at Suzy and said, "I think he is ready for your tight, wet, little pussy dear." So Suzy slid down the couch and onto the floor on all fours, saying "Fuck me from behind, doggy style." So I slid off the couch, got behind her and probed her until my cock found her wet pussy. As I pushed my cock inside, I met a little resistence. Her pussy was so tight, and my cock so hard and big I was worried I would hurt her, but she backed onto my cock, making me shudder with excitement.
Because her pussy was so tight, there were several times when I slammed my cock so hard into her that she screamed, almost as if she was in pain. I would stop and slow down but she kept saying "Fuck me, as hard and deep as you can. Treat me like your little slut. Make me hurt! Fuck me harder, harder baby!" And this kept going on and on, making her cum hard and shudder under the rhythm of my cock sliding in and out. Finally when I could take it no more I started to pull out because I was going to cum. Almost as if on que her mother said "No, no. Don’t pull out. Fill that tight little pussy with your cum!" Suzy looked back at me and agreed with her mother saying "Really, its okay. I am on the pill. Pull out now and I'll kick your ass! Press hard when you cum, I want it deep inside my tight little cunt!" So I started fucking her harder and harder till I finally couldn’t hold back anymore. Like a flood that has been waiting for centuries, I cam so hard and for so long that I was sure it would shoot out of her mouth before it stopped. Suzy kept screaming "Oh My God! That is so much cum! Oh My God! Oh My God! Mom, what did you make me do! This isn't right! Oh God that feels so good. I can’t take anymore." I shuddered and shuddered, pressing my cock in hard each time I felt more cumming out. Finally I had emptied myself of my reserves and just sat there, my cock still burried deep inside Suzy. It finally registered with me that Suzy had screamed at her mother about what she had made Suzy do. I asked what they meant by that and they both looked at each other with wonderment. Then Suzy's mom said "She is not really on the pill. By my math, I think she is ovulating. It is very likely that you just got her pregnant." I was dumbstruck. Suzy looked over at me and said "I really wanted it at first. But when I felt how much you came, I got scared. Now I am not sure I want to get pregnant. But we will make it work what ever happens". I didn’t know what to say. So I just sat there. After a while I just smiled and let my worries float away. I had just lost my virginity to my cheerleader friend, with her mother in the room participating and likely knocked her up, with her mother's permission and though with a little apprehensiveness, Suzy's permission too.