A Bet is a Bet

My name is Sally Anne. I won’t tell you my last name because then you will know who I am. I am almost 19 years old now. I wanted to tell all of you about how I lost my cherry. I don’t know why they call it a cherry. It doesn’t look anything like a cherry. You think calling it a peach would have been more appropriate.

It was right after I turned 16 and I still had my stupid braces on. God, how I hated those braces! Anyway, if you have ever had braces on, you know how restrictive they are when it comes to things like blow jobs and kissing. Most of the other girls in my class were into the blow job thing big time and I had to listen to all this talk about: using your tongue, trying not to gag, swallowing or not swallowing. I wanted to get in on all the fun real bad, but most of the boys were immediately turned off as soon as they saw a mouth full of metal.

Even kissing was elusive because of my brace issue. I had a girlfriend called Lisa who had an older brother. His name was Josh and he would kiss me all the time as long as I kept my lips nice and tight together. He also loved to push his finger into my poopy hole and act like nothing was going on. Believe me, when your poopy hole is being stretched by anything, it is like a major event.

I wanted to suck Josh’s cock so badly that I even begged him to stick it in my willing mouth. He was much too afraid to take that kind of risk.

He did let me take it in my hand and I jerked it and did exactly what he told me to do to make him feel good. His sister Lisa came into the bathroom and saw me on my knees and giggled nervously. She was careful to keep the noise down because her parents were downstairs watching some silly reality show. I could see she was real interested in her brother’s cock. I figured she wanted to get a hold herself, so I turned it over to her. I started to feel Josh’s balls and even ran my hand back to his ass crack. I was surprised when he cried out and shuddered like he was shivering from the cold. I looked up at Josh’s face and he had this really weird look.

The sudden splash of warm cum hit me right smack dab in the nose and I shut my eyes real quick so I would not get any in my eyes. I could feel it all dribbling down my face and onto my school uniform. Both Lisa and Josh were stifling their laughing as they looked at me. I looked in the mirror and I had to laugh as well. I looked so silly with all that creamy cum dripping down off my face. When I smiled, all you could see was dripping semen and a mouth full of wire. We all sat on the bathroom floor laughing as quietly as possible.

Lisa became my very best friend and I would often join her and Josh in “studying” in her bedroom. I loved to watch her gobble up Josh’s cock and swallow all of his creamy cum. I was so envious of her. I was happy with jerking Josh off and letting him finger my poopy hole as deep as he wanted. Sometimes he would playfully slap my ass cheeks. I didn’t let on how much I loved that because I thought they would both think I was perverted or something.

We got into this thing of me shoving some of my fingers up Josh’s tight butt just as he was getting ready to shoot his stuff into Lisa’s mouth. Lisa loved the force of his cum, Josh loved how it made him tingle all over and I have to admit I got real wet all over my panties whenever we did that.

I was still kind of naïve and innocent like because I still had my cherry and no other boys were willing to risk putting their cocks in my mouth.

Then, just before Halloween, I was invited to a sleepover at Debbie Lickitt’s house. She had a real big house. It was almost like a mansion. There were about 6 girls from my class and even Lisa was there. I was real happy to see someone I really like a lot at the party. I figured there were no boys allowed and was surprised to see Josh and a couple of other boys diving into the pool out back with Debbie’s older brother Todd. I was the youngest one there and, like I already said, I was past my 16 th birthday.

A couple of the girls were teasing me about my braces and I was not really enjoying myself all that much.

“Put away the magnets, here comes metal head.”

As you can imagine lots and lots of belly laughs.

Even Lisa joined in and said,

“When Sally Anne smiles, it looks like a hardware store.”

That one really hurt, but I could see my best friend was just trying to be one of the girls.

Debbie looked real bored.

“Let’s play a game. Everyone get in a circle and hide your heads with these bags.”

She handed each of us one of those really big paper bags from the grocery store with a hole cut out for the mouth and two holes for the eyes. All of sudden, we were all incognito. I am not really sure what that word means but I think it means like unknown.

“Now down on your knees and elbows and close your eyes.”

I peeked into the full length mirror on the closet door and my heart starting beating real fast when I saw 7 young girls with their asses sticking up high in the air and their heads covered completely by paper bags. It was really hard to tell who was who.

I saw Josh, Debbie’s brother and the other two boys come into the bedroom and they had all removed their swimming trunks. The sight of those erect cocks made my pussy start to leak right away.

“OK, girls. I am going to play my musical chairs music and my brother and his pals are going to walk around behind us and stop when the music stops. Whoever they are behind must accept their fingers, hands or cocks rubbing all over their bottoms.”

I heard all the girls giggling and one girl kind of sobbed and said,

“Do you mean we have to take a cock up our ass, Debbie?”

“No, you silly twit. Just rubbing in the crack and all. This is a game, not an orgy.”

I was a little bit nervous but it was too late to back out now. The music started and then stopped almost right away. I heard some of the girls squealing and crying out as they got ass played but I was not involved. This happened a couple of times and then when the music stopped, I felt a huge cock placed right on top of my baby doll pajamas. The head of the cock was rubbing right at the top of my crack on my bare skin. It felt so nice; I pushed up high to get it on me real hard. A pair of hands eased down my bottoms and the pre-cum lubricated cock slid up and down my “hot to trot” ass crack.

A couple of well-placed smacks on my ass cheeks made me certain it was Josh playing with my innocent ass.

A bit later on, I was a winner again and this time the boy pushed two fingers up deep into my pucker hole. I wonder if he knew how much I loved that. I pretended to be all reluctant like and begged him to take his fingers out of me.

“Oh! Please! Not in my poopy hole. You are in too deep. How many fingers did you put in? I never take anything in back there. That is so nasty. Please don’t make me take it.”

Of course, I was having a ball and dreamed about someday getting stretched by Josh’s huge dong of a cock back there.

All the girls thought this was a fine game and we were ready for the next stage of the festivities.

I noticed that a couple of the girls had removed their tops and Debbie was completely nude wearing only her slippers on her feet. I removed my bottoms because I was still a little self-conscious about the size of my small breasts. I did think the nipples looked very nice but I needed a little more filling out to make them sexy.

Debbie told us we would all have to draw a card from the deck and that the highest card would have to submit to a nice fucking by her brother. I figured it was a pretty safe bet because I had only a one in seven chance of getting humped by that monster cock.

I was wrong.

You guessed it. I drew the Ace of Spades. When I saw that card, I knew it spelled the end of my cherry. The end of my innocence. I was secretly delighted, but still so frightened that I begged for mercy like a silly little schoolgirl.

“Please don’t make me do it. I will do anything. Please don’t let your brother fuck my pussy.”

I should mention that at this point, we all still had our paper bags on our heads. Well, all except for Debbie. She was the hostess and needed to direct things. 2 of the girls grabbed hold of my arms and held me immobile between them. I felt something banging into my paper bag and was shocked to feel the tip of a wet cock coming through the mouth hole onto my lips. I couldn’t believe it. This is exactly what I wanted so desperately.

“Open up that mouth, you little bitch! Start licking with that schoolgirl tongue. You are such a little slut. Open up wide and take my cock in your mouth.”

Debbie’s brother was so well-hung that I knew I could never take the whole thing into my mouth. I covered my teeth and braces with my lips and opened wide. I made little circles around his shaft with my wet tongue and was rewarded a few squirts of pre-cum onto my taste buds. He was starting to penetrate back into my throat and I was afraid of gagging at a time when I wanted to give him the most pleasure. I applied forceful suction and blew my hot breathe all over his tool. It jerked like a drop of butter on a hot griddle and I received the first spurt of his creamy warm cum in the back of my throat. I swallowed as quickly as I could and did not waste a single drop. I licked his cock clean and he pulled it back out of the paper bag. I had finally lost my oral cherry. Now it was time to get down to the real business of losing my vaginal cherry. It was the unwanted membrane blocking passage to a world of pleasure awaiting me.

All the other girls had taken off their bags and I was the only one left with a bag on her head. 2 of the girls had my arms and now 2 more of the girls wrapped their arms around my knees and made me spread my legs wide open. I was really scared now but I knew it was too late to reverse course.

Debbie and another girl started to lick and kiss my little hard nipples. They were so tender and sweet that I began to leak big time from my pussy. Lisa pulled the bag from my head so I could see Debbie’s brother ease his cock between my legs and up against my pussy lips. I was starting to tremble both from fear and excitement and started to protest, but Lisa pushed her lips against mine and made me open my mouth to receive her tongue dancing in sensual impalement of my oral cavity. I could feel fingers from a couple of the girls probing my pulsating anus with terrible familiarity.

The touch of that cock on my vaginal slit was electrifying.

I writhed in erotic ecstasy pulling against all 7 girls holding me down. They knew I was going to get it hard and deep and they held on tightly to my gyrating body.

The cock slid inside me relentlessly. It paused only momentarily at the obstruction of the fragile membrane. I gasped and took it all in.

I was a woman now.

The impalement was final. My ass cheeks trembled with excitement. I could feel my anus clutching at the female fingers stroking it so deeply. I milked that delicious cock for every last little drop of creamy cum. My nipples were being twisted and nibbled now by two very demanding girls with sharp teeth. I was pushing my tongue into Lisa’s mouth showing her who was boss. She gave it up to me with complete submission.

When the cock was pulled out, all the girls’ ooowed and ahhhed at the seepage of creamy cum visible at the entranceway. One after another, they all pushed their heads up between my legs and ate my delicious creampie. I kissed each of them and licked the cream from their teenage lips. Debbie’s brother and the rest of the boys watched us in amazement as we intertwined in a jumble of female lips, pussies and soft, curved asses. For the rest of the night, the boys had fun taking us in our mouths, our asses, and our not so innocent little pussies. Before the night was over, I had given all the boys repeated blow jobs. None of them objected to my braces, so I guess it was all in my own self-conscious mind after all.

Still, I was happy when those darn braces finally came off.