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Introduction:

Gail gets her cherry popped, I confirm a hunch and get my summer job
Summer of 79- Chapter 5
Gail was knocking on my door bright and early the next morning. I let her in and she followed me into the kitchen. “You want some coffee?” I asked as I poured myself a cup.
“No, I don’t drink coffee but I’ll take some water.” She said.
“There’s a jug of ice water in the fridge.” I said.I noticed she was in her Speedo again. “How was practice?”
Gail was bending over looking in the fridge for the water said something about the coach not being there and that Vicky had run the practice this morning. “God, she’s a real bitch today! I don’t know what’s wrong with her. She said something about the board of directors sticking their noses in her business. She finished as she poured the ice water into a glass and sat down at the table. Her nipples were popping out from the cold of the refrigerator and I thought they looked so kissable my cock started to rise in my gym shorts. I sipped my coffee and said “She offered me a job in the afternoons yesterday just before the board meeting, I think I’m going to take it too.”
“Oh wow, really? That’s great, I’m so happy you’ll be there to save me if I start to drown or something!” Gail said.
I laughed and said. “Like that’s going to happen! You know something, sometimes you are a smart ass.”
Gail smiled and asked. “What are you going to do, spank my ass like you did to Mary Anne yesterday?”
I froze with my coffee cup half way to my mouth, looking at her. “Whaaa, how do you know about that?”
“Well, yesterday you kicked me out so fast that I forgot my panties and came back for them and heard her screaming and saw what you all were doing through the window on the front porch. I was so wet from watching you fuck her that by the time I got home I practically had to ring my shorts out.” Gail said. “That’s what I want you to do to me, the same thing you were doing to Mary Anne.”
“How much of that did you actually see us doing?” I asked. “I really hope you know enough to keep your mouth shut Gail. You could really fuck things up for Mary Anne.”
“Oh, I wouldn’t say anything to anyone else but I did see her sitting on your lap and then you put her on her hands and knees and fucked her from behind.” She said eying the lump in my pants. “I also saw her suck your cock after you were done. Do all girls do that?”
“Not all of them but some girls like the way it tastes afterward.” I explained. “I don’t really like being spied on Gail; maybe I should give you some of the same treatment I gave Mary Anne yesterday. Take off your suit and come over here”
Gail looked at me and didn’t move for a few seconds. “Do you remember what I told you yesterday about listening to me and doing this my way?” I asked. She shook her head yes and stood up in front of me. Gail lowered the straps of her Speedo and started to pull it down her slim body, she turned away and bent over as her suit lowered down past her tight little ass. I grabbed her and pulled her over my lap and; SMACK! SMACK! SMACK! SMACK! I put four good swats across her ass, two per cheek.
“OW! Hey that hurt! What did you do that for?” Gail asked with tears running down her face. Her ass was turning a bright shade of red and you could clearly see my hand prints on her cheeks. “Fucking shit; that stings!” she was rubbing her ass.
“Well, you said you wanted me to do to you what I did to Mary Anne and the first thing I did was to spank her ass, then I made her suck my cock.” I told her. “So you may as well get down here on your knees and suck my cock little girl.”
“Aren’t we going to go back to your room and make out some first? I didn’t know you spanked her.” She asked while still rubbing her tender ass and looking at the growing bulge in my shorts.
“Mary Anne is one of those people who like to be spanked Gail, she also likes rough sex as well as doing other, much nastier things in or out of bed. And she also likes to be treated like a fuck slut at times, at least by the right guy. We have been really good friends for a long time, sometimes with “benefits” sometimes without. What we do is only on occasion and she knows that I’d never really hurt her. She comes to me because she knows she can trust me to not blab it all over the place and ruin her reputation. Can you imagine what her boyfriend would do if she told him she liked that kind of thing and then they broke up? He’d waste no time at all putting the word out all over town, the school, everywhere she would be ruined and so would her family. I’m asking you now, as a friend to please never say anything about what you saw us doing yesterday Gail. I need to be able to trust you on this. Ok?”
Gail was kneeling at my feet as I explained things to her and she looked up into my eyes. “Oh, I’d never say anything to anyone Chris, after all, I don’t want you telling Ricky that I’m getting sex lessons from you. But would you please never spank me that hard again?” She said.
“That’s a good girl.” I said holding out my arms out to her for a hug. “Did you like getting your ass spanked?” I asked as she came into my arms. I already had a feeling Gail liked her ass being played with and just wanted to hear her admit it.
“Well, I kind of liked it but not that hard. It really made me feel hot when you licked and played with my ass yesterday. Are we going to do that again today? She asked looking like little kid asking for ice cream as I stroked her ass and squeezed her left cheek.
“Do you want to do that again? You want to suck my cock and have your pussy eaten out?” I asked her.
“God yes, last night I couldn’t stop thinking about how good it felt. When I woke up there was a wet spot in my bed.” She said turning red.”Will you do that thing to me with your tongue you did yesterday? That was so nice.” She purred. I picked her up holding her ass in my hands and giggling; she wrapped her legs around my waist as I walked back to my bed room. She was kissing my neck and purring in my ear as I slid one of my hands further under her enough to push the tips of two fingers into her sticky wet pussy.
“Mmmm, I like that. If you eat my pussy for me like yesterday I’ll suck your cock.” She whispered in my ear.
I chuckled at her and said. “That sounds like a good trade.” As I pushed my fingers up inside her and stroked her G spot. I laid her down on my bed and with a big smile on her face she spread her legs wide apart for me. I pulled my shorts down and laid down between her legs with my face right at her tender blonde haired pussy, I could see she was really wet, her juices had started to run down onto her asshole and her clit was poking out of her lips at the top of her pink slit. She smelled kind of like Flex shampoo and aroused woman. I kissed her right on her button and she gave a sigh and ran her fingers through my hair, pulling me closer to her eagerly drooling pussy. Using my thumbs I pulled her outer pussy lips apart, exposing her hole and her hard little clit, her inner lips opened like a flower and I ran my tongue all around them, up over her clit and headed back down to her hot, tight pussy hole. Gail’s hips were moving now and she was making noises that sounded like whimpers and moans as I worked my tongue in and out of her hole. She was really getting hot and her pussy juice was running out of her, coating her pink little puckered asshole so that it was shining at me, begging me to lick it. I couldn’t ignore it and went down for a taste of her musky, sweet asshole.
“Oh yeah, do that again! Oh my fucking God! I like it when you lick my pussy and ass all at the same time!” She hissed. I came up for air and lay back on the bed.
“Put your keens on either side of my head facing me feet Gail, now start sucking my cock like you were yesterday.” As she got into position I said. “We are going to do what is called a “69”, that’s where the guy eats the girl’s pussy while she sucks his cock at the same time. Think you can handle that?”
“I’ve heard some of the girls mention doing a “69” before but I never knew what it was. Sure, I’ll try it.” She said as she swung her leg over my head and got into position. I looked up and Gail’s furry blonde pussy was staring me right in the face, it was wet and runny with her female juices and her scent was making my mouth water for another, longer taste of her. I put my hands on the cheeks of her ass and pulled her sex open as I kissed and sucked at her pussy hole and tried to push my tongue as far into her as I could. Gail started sucking my cock like she’d been doing it for years. She had a mouth like velvet and I never felt one tooth graze my cock. She was pumping my cock in her hand and following it with her hot little mouth the way I had told her to do yesterday and her tongue was everywhere all at once. I decided to test a theory and stuck my finger in her hot, wet pussy as I was sucking her clit, when it was good and wet I took it out and started working it around her tender, pink, puckered asshole. Gail started jacking my cock harder as I was licking and tonguing her cunt hole while I started to probe her ass with just the tip of my slippery finger. She started to push back against my finger and I pushed some of it into her tight warm asshole as I went back to sucking her clit. Gail tried to swallow my cock and started moaning on my shaft. The vibrations on my cock were too much and as Gail started to cum and grind her pussy on my face I let go and shot a big load of cum into the back of her throat. She tried to swallow all of it but there was just too much and some of it was leaking out at the corners of her mouth. Gail started coughing and rolled off of me onto her back on the bed, when she had gotten her breath back she looked at me and said,
“Wow you sure do cum a lot! I thought I wasn’t going to be able to eat it all.”
I smiled and said. “Look who’s talking, the way you came all over my face I thought I was going to drown. Let’s take a break for a few and do some hits.”
“Man that shit really knocked my ass for a loop yesterday, I was still high at dinner time. My mom and dad were asking me what was wrong with me all last night. Maybe I shouldn’t do any.” She said
“Maybe you should do some just not as much as you did yesterday Gail. Christ girl you did like 6 bong hits, which would have toasted me and I outweigh you.” I said laughing.
“OK then but I’m only going to do like two hits with you, I don’t want to get stoned and get caught by my parents.” She said sitting up on my bed and tucking her feet under her. I got the bong out and loaded up some hits for us. A few minutes later we were nice and buzzed.
“So today I was thinking we’d try something different and new. I think you’ll like it. What do you say, you ready?” I asked.
“Sure, what do you want me to do?” Gail asked with wide attentive eyes. “Well I want you to lie back on the bed.” I explained. “Good, now bring your knees up and catch a hold of the backs of them with your hands.”
“Like this?” Gail asked as she rolled onto her back and grabbed the backs of her knees and pulled her legs up almost to her small titties, exposing her sweet pink slit and asshole to me. Gail’s pussy hair was so fine and so blonde as to be almost nonexistent.
“Good girl, yeah just like that.” I told her. I crawled up on the bed between her legs. I took my hard cock (which had never gotten soft) in my hand and tapped it on her drooling pussy lips a few times. She had her legs together and I pulled them apart so I could see her face and started sliding my cock in between the lips of her hot, wet pussy.
“Oh, that’s nice.” She cooed. “I like it go faster.”
I sped up and pushed my cock against her pussy lips and clit harder. Gail’s hips started to rock back and forth in time with my thrusts and she really started getting into what we were doing. She was rocking her hips back further each time that I pulled my cock through her lips and picking up speed when it happened. Gail’s eyes were closed and she rocked back just far enough as I pulled back that on my next forward thrust I slid right into her hot, dripping virgin pussy almost up to the hilt, tearing through her cherry in one swift forward thrust. Her eyes shot open and she cried out. I stopped and let her get used to the new sensations that were running through her body. Tears had formed in her eyes and ran down her cheeks and she kept opening and closing her mouth like she was trying to catch her breath.
“Shhh, shhh, it’s ok, I know it hurts right now but it won’t for long baby.” I told her looking into her wide blue eyes. “Sorry I surprised you but I don’t know any way to do this that isn’t painful to some extent.” Gail was crying but she flexed her hips and tried rocking them some.
“It did hurt but not as much as I thought it was going to.” She said while gently rocking her hips in shallow movements. “You just really surprised me more than anything is all. God it feels like you are going to poke out of my belly button!”
“I’m sorry baby, it was kind of a surprise to me too, I usually time it differently but you rocked your hips back just far enough and we lined up just right and I didn’t realize it till I was inside you.” I shifted my hips and pulled back slightly as she was rocking hers and my cock slid out then I pushed forward as she rocked forward and I slid back in. we did this slowly for a few moments, I was trying to let Gail set the pace of her first time fucking and she seemed to be getting the idea. As she started getting more used to having my cock almost all the way up inside of her cunt she began rocking her hips a bit more aggressively. I pulled more of my hard cock out of her and let it slide back into her wet hole. I still had about two and a half inches that had never been inside her sweet tight virgin pussy and was going to work the whole thing into her if I could.
“Mmmm, ah yeah, go a little faster Chris.” Gail moaned to me as she worked her hips on my shaft. Her pussy was so hot and slippery and tight that I was glad I had blown a load down her throat earlier. I started thrusting into her faster. I looked down between us to where we were joined and watched as my cock pulled out of her pussy, dragging her inner lips around the shaft. Like a lovers lingering kiss. When I pushed back into her they rolled back and into her. I pushed into Gail’s pussy as deep as I had been and worked my hips, grinding into her hot, tender, willing pussy. I pulled back and short stroked her hole with fast shallow thrusts before slamming back into her and pushing the last few inches of my steel hard cock through and into her womb. I could feel that extra little ring around the head of my cock and knew I was as deep into her as I could get. I held my cock in her and worked my hips in a half circle to the right, then back to the left. I moved my hand from the back of her thigh and onto her exposed clit and flicked it back and forth as I pulled my cock from her depths and started to set up a long steady stroking rhythm into her.
“Oh, oh, oh yeah! OH MY FUCKING GOD! Keep doing that, yeah, yeah, yeah! Shit I’m going to cum again! OH GOD YOU’RE GOING TO MAKE ME FUCKING CUM ALL OVER YOUR COCK! Don’t stop, don’t fucking ever stop fucking my pussy!” She yelled. Her body started to shake and her eyes rolled up as she came all over my hard thrusting cock, squirting pussy juice onto me. I could feel the muscles of her pussy gripping me and I just let myself go and dumped a load of hot sticky cum deep inside of her newly fucked hole. I rolled over onto my back, pulling her on top of my and just laid there with my cock still up inside of her twitching pussy. I stroked her hair and ran my hands over her back trying to catch my breath I could feel my cock going down and moved Gail off of me and onto the bed.
“I’ll be right back little one.” I whispered to her as I got up and went into the bathroom. I cleaned myself up a bit and came back to Gail with a warm, wet washcloth and started wiping the cum and blood off of her pussy and inner thighs.
“Oh God that feels really nice.” She murmured as I cleaned her up. I held the warm cloth against her freshly fucked pussy as she sighed.
“Mmmm, oh shit, now I have to go pee. She said as she rolled over to the edge of the bed. As she stood up a bunch of cum mixed with her pussy juices and blood came out and started running down the inside of her thighs. “Oh my God, there’s so much of it and my legs feel like rubber!”
“Come on, we’ll get a hot shower and get cleaned up.” I said with a chuckle as I stood and took her hand to steady her.
My family had started a business a few years back and one of the very first things mom and dad had done when the business had started making good money was to have the kitchen and bathrooms in the house remodeled as well as having an addition and raised deck put onto the house. We had a huge shower with a separate whirlpool bathtub large enough for two (Large) people. Last year mom and dad had a hot tub installed out on the deck outside and there had been a few nights this past winter when dad had asked me quietly and with a wink if I would please stay with a friend overnight. Things seemed to be going good for them because they were always in a really good mood the next day when I got home.
We got into the shower and I washed Gail from top to bottom, paying extra attention to all her girly parts, especially her sweet ass. When I was finished she did the same for me and spent extra time washing my cock with her soapy hands. She soon had me standing up hard and ready to go again and I picked her up in my arms, she wrapped her legs around my waist and I lifted her up so that the head of my cock was lined up with her pussy. Gail put her arms around my neck as I lowered her onto my stiff shaft and began to slowly fuck her tight young cunt in the shower. The water started getting cold after a while so I shut it off and carried her out of the bathroom still impaled on my rampant cock slowly grinding it into her overheated pussy, bumping it into her cervix and making her squirm and moan. As we came out of the bathroom the phone started ringing so I went into the kitchen and sat her on the counter as I answered the phone while I was still deep inside of her. It was Vicky, she’d called to let me know I had been approved by the board for the life guard job.
“Hey Chris you got the job!” She said over the phone.
“Great, when do you want me to start?” I asked, pushing into my little students willing pussy while she cat on the kitchen counter.
“Rub your clit while I fuck you baby.” I whispered in Gail’s ear holding my hand over the mouth piece of the phone.
“Well, we are closing early tonight because I have to back flush the filters and I was hoping you could come up and give me a hand doing it so technically tonight.” Vicky answered.
“Ok, I’ll be there. What time?” I asked as I started thrusting into Gail harder, making her ass bounce on the counter.
“Come up around seven thirty.” She said
“Alright, I’ll be up sometime today to do some diving but I’ll make sure to be back up there by then.” I told her. We said goodbye and I hung up the phone just as Gail let out a loud wail and started shaking on my cock as her orgasm hit her.
“I want to taste your cum again Chris. Will you cum in my mouth, please?” She asked me. I pulled out of her hot pussy and she hopped off the counter to her knees on the kitchen floor and took my cock in her sweet mouth, she pumped the shaft several times while she worked her tongue over the head while I looked down at her. Gail looked up at me with my cock in her mouth and those blue eyes of hers. It was just so sweet and hot looking seeing her like that I couldn’t hold back any longer and gave her what she had asked for, blowing a third load of cum into her. This time she didn’t miss a drop and licked my cock clean before she was done.
“I guess you heard that, looks like I’m going to be one of your new life guards at the pool.” I said as I held out my hand to help her up.
“Wow that sounds great Chris, I’m so happy for you.” She said
“Yeah, I’m kind of happy to be getting something to make some money at this summer.” I said smiling
“Does, does this mean my lessons are over?” Gail asked in a small voice looking down at the floor.
“No sweetie, I will be working the afternoon, evening side so we can still continue with your lessons but you are just about ready now.” I said hugging her to me. Gail looked up and was smiling from ear to ear.
“Gosh, you really think I am?” She asked. “I wasn’t so sure.”
“Well, it’s only Wednesday so that will give you two more days of practice and I’m pretty sure you’ll be ready for anything Rick has in mind for you by then kid.” I told her patting her ass as we headed back to my room. “Come over tomorrow at the same time. Sound good?”
“That sounds good to me.” Gail said smiling as she pulled on her Speedo and stepped into her flip flops.
I slipped into my own Speedo and threw a pair of shorts on over them along with a T shirt and sandals (I never have liked flip flops) and grabbed my keys.
“Hey Chris can you give me a ride to Leah’s house please?” Gail asked batting her pretty blue eyes at me.
“Sure, I suppose I can. Hey how come Leah never liked me? I have never done anything to her and she’s always acting all stuck up around me and giving me these looks like she’s better than me and I’m some kind of insect. It really pisses me off sometimes.” I asked.
“I don’t know, she’s like that with a lot of people but she’s my best friend and she’s really a sweet girl once you get to know her.” Gail said as she picked up her beach towel and bag.
Yeah, but she just has that attitude and no one ever wants to be around her because of it. I gotta tell you she’s a fine looking hottie and a lot of guys wouldn’t mind asking her out. The only thing that holds them back is her acting like a bitchy stuck up snob all the time. I know a lot of guys who think she’s hot as all get out but won’t go near her because of the way she acts.” I told Gail as we drove the three blocks to Leah’s house.
“I know, and she wasn’t always like that. Ever since she started… well she started to become a woman she’s been like that. Gail told me. “I’ll try and talk to her, she’s really nice once she knows you.” See you tomorrow she said as she got out and headed up the sidewalk to Leah’s house. I pulled away from the curb and headed up to the pool thinking to myself, “That I now knew for a fact that little Miss Gail liked to have her asshole played with and I was hoping I could talk her into letting me have her ass as a way of paying for her “lessons”, maybe not by Friday but sometime soon, very soon.
3 comments

Bear62Report 

2015-03-24 14:21:29
More of this story is on the way, this is my busy time of year, sorry about the delays.

Bear62Report 

2015-03-17 00:48:25
Thank you, I'll keep that in mind for further reference so the same mistake is not made again.

Anonymous readerReport 

2015-03-16 21:21:41
In the abscence of an extreme anatomical anomaly it would not be possible for the penis to enter the cervix. Quite simply it lacks the rigidity to accomplish this. In order for the penis to penetrate the cervical os it would need to be quite a narrow diameter and the penis would would require an actual "bone."

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