Kerry wants Her Cherry Popped

Then, Jennifer, a Black Girl in our group, tell us, she decided she didn't want to go off to college as a virgin, so she let her boyfriend, fuck her after the homecoming football game behind the bleachers. She brought out a large blanket, on the ground, they undressed, started making out, he starts feeling her 36C breasts playing with her nipples, they're both getting all hot and bothered, he takes his 10.5 inch large girth penis throws on a large and big condom and wants to enter her -- she see his girth trying to figure out how that monster will fit into her virgin hole and all of a sudden he sticks it in , ouch and starts pumping away, she has a small orgasm, he cums, they clean up and she never hears from him again.

The Society members & other teens, also were telling stories around school, about college boys, picking out the Freshmen Girls that they found out are virgins, and having sex with them just for the fun of it, then mentioning it to everyone, keeping score, some even taking pictures then posting them to the internet. I don't want any of this drama mom and if you recall when I discussed boyfriends you, after I turned 18, I mentioned that the boys in my school act like in-mature babies especially when it came to sex, so I decided I want to find a Mature Man to deflower me and maybe date.

You know Mom, Kerry continues, Kathy cannot believe the details these teens are giving each other about their sex lives & future sex lives, but she continues to listen to her daughter talk, as Marcus continues listening in, his 7-inch pencil dick is starting to get harder, as he starts getting more excited, drawing his running shorts down, he begins to pump slowly at first on his penis, continuing masturbating while his twin sister, describes girls from his school getting their cherry popped in detail.

Marcus starts to think, that Maryann has never mentioned this club to him, so he only can hope that his girlfriend is also a member of his sisters secret after school club, so he continues to listen, slowly pumping his dick tightening up more his hand, he pays more attention to his sister's conversation.

Kerry then says to her mom, you know this is a secret society that we started for us 18-year-olds to help each other learn about life. So, please DO NOT SHARE anything I say with anyone else or tell Marcus, what I am about to tell you, what Maryann told me.

If you recall, Kerry, as a mutual Valentine gift to each other, after Maryann turned 18 in early February, the two modeled together, finishing the project in the nude, for the painting they wanted, of each other together with their hands around the other's waist, that is hanging in both Marcus's & Maryann's bedrooms.

We know Maryann, is shorter than Marcus about 4 ft 7 inches and she is really cute, hardly any boobs, with a bob style short brunette haircut.

With that Marcus who has been slowly pumping away, almost ready to cum immediately stops what he is doing to listen closer, almost placing his blonde head into the same room, you know Marcus's girlfriend is still a virgin, Kathy says, I often wondered about them two, I am sure they have explored each other's body, fooled around some, but I wasn't sure how far they have gone together.

I let them both be alone together in his room, part of our family openness. I know mom, as his twin sister, I have even perved into his room totally nude, quietly opening the door, they were so busy, they didn't know I was watching, I even started rubbing my pussy!

Kathy, kind of raising her voice to her daughter, I know we have an open policy in this household but that is going to far. I have only done it a couple of times then stopped, to give them total privacy. I know I was wrong but it was fun, I have seen Maryann's nude body many times, well mom, even I have fooled around with her as well. Mom, sometimes I wish it was me under his sheet with or without Maryann in the bed. Kerry, what has got into you, we have got to find a man to fuck your brains out.

Kathy gives her daughter a look, listen mom nothing serious with Maryann & I, I am not a lesbian and she really likes Marcus, but early in their relationship, she wanted to practice kissing before she started kissing Marcus and well we got to see each other nude, then decided as she liked my boobs, compared to hers, felt each other's boobs and that is when we decided to stop.

Now we have just been really good friends, we talk, I told her about my thoughts on having sex with an unknown mature man for my first time, so I could learn about sex as well as enjoy it and she wanted to hear all the details after, as she wants to remain Marcus's girlfriend. Kerry relates her story and conversation with Maryann to her mom.

She is looking forward to their vacation with her parents to St. Barts, she cannot wait to run around nude with him on the beaches and he doesn't know until they arrive but since her parents are all cool, free spirited and open like you, they said it is ok if they slept together in the same bed, maybe she will have sex with him or at least get to play around further in their room. Kerry continued; Maryann is also afraid of being stabbed with his 7-inch long pencil dick that depending on how long she plays with it, it grows a little bit more.

She has sucked on his penis, getting as much as possible into her mouth before choking while trying to swallow his load when he squirts his ropes of cum, she has even masturbated him allowing him to squirt on her breasts, then letting him lick it off. He has sucked on her bite size breasts. Heck, mom, she has even had him go downstairs, licking her pussy, and she says, he is not bad at it. She has even had small orgasms from him.

Upon Marcus hearing all this, hearing how he sister perved on him & Maryann, even playing with her a little, but especially now after hearing about giving Maryann the orgasms, he starts pumping his dick really hard that it is almost hurting, thinking about his times with Maryann and the fun they have had so far with the upcoming fun she has planned for him on their trip.

He cums immediately, squirting and squirting, trying to use his running shorts to catch his white liquid load, cums again starting to leak, he then runs upstairs so he doesn't get caught. Not saying anything to Kerry, Kathy let's out a small laugh, as from her position in the sitting position she is in, as she is facing the staircase leading upstairs, catches Marcus running up the stairs with his running shorts covering his penis.

Kathy asks Kerry if she liked kissing and feeling up Maryann and her daughter told her it was ok, but I would like to try with a mature man first, have his hands over my nubile teen body and kissing my soft lips, then pushing into my wet moist virgin pussy and deflowering me. However, it was nice kissing Maryann, I will say that and Marcus is lucky to have her.

Maryann says she wants to have sex and go further with Marcus but is afraid of them both not knowing what to do and I don't currently have a steady boyfriend, so I again mentioned to her and members of the society, that I decided I would prefer a mature man that knows what to do and make it easier for me.

Listening to her daughter talk, with her nice boobs, directly at her eyesight, she notices for the first time, the tan lines, some white around her nipples, from the spray booth and the long, like hers, nipples that are elongated, never thinking of her daughter as a sexual being, since they started having the freedom to go nude around house, plus also thinking about the session with Mrs. Anderson, Kathy's own pussy moistens, hopefully her daughter won't recognize or notice the sexual odor in the room coming from her mom's pussy.

After their almost two-hour conversation about sex, deflowering etc, Kathy tells her daughter she will place the advertisement, in the web version only, artists for model's publication classifieds. Several things Kerry and listen to me very carefully, I'd rather you be safe and enjoy your first time, so I am agreeing to this. Next, I am going to photograph and video tape your first time, so you can enjoy it at a later time in your life, you may even want to share it with your husband, whenever that time comes in your life.

I know we have been free around here to be nude, however, when it comes to shooting around a strange man, you will have to be shy being nude at the beginning of the session, you will wear a disposable paper G-string under your robe, cover your breasts for a minute or two after you take off the bra and act more shy when the G-string is removed. You can watch the modeling session either live off to the side quietly or on our close circuit TV.

You can stop the session at any time if you start feeling uncomfortable. I am going to have him touch and rub your breasts, nipples and touch your body. I won't know all details until we meet him and jointly decide he is the one. You agree to all this, yes mom, I am even getting excited and can't wait.

Finally, we jointly discuss if this will be the man and you will wear an eye mask through-out the session. As far as the male model is concerned this is all for a special client and NOT my daughter. Do you agree, Kerry let's out, as she salutes her mom, she yells out Yes ma'am, I agree to your terms and conditions to allow me finally getting fucked.

As Kathy looks over at her daughter, she pulls her over into a great big bear hug giving her a non-sexual but loving kiss on the lips, saying I love you Kerry and I even love more the open relationship that we have and we both even have with Marcus, except for the part about Maryann - TMI, Kathy breathes out under her breath so Kerry doesn't really hear her, only somehow I think she hears. I wish your dad was still alive to join us in these open conversations, I know we all miss him.

Kathy tells Kerry, the plan is, that we place the ad, mutually decide on the person and if all works out, when Marcus is away in the beginning of next week, vacationing, with Maryann and her parents that we will schedule the session. Who knows, maybe Marcus will get lucky or maybe she will wait to give her virgin pussy to him. Twins deflowered in the same week!

Kerry then tells her mom, when I told Maryann about my plans, hoping you would film it, that Maryann told her that she may wait to hear what Kerry has to say, when she gets back from her trip, to hear about how my deflowering with a mature man went and how much pain I experienced.

Maryann mentioned she may even watch the video, with or without Marcus, they can both learn together and practice from my video. Kerry, don't get a head of yourself, and you wouldn't object to your brother seeing you getting your virgin pussy plugged for the first time. Why not mom, we are both very close, I have seen him nude, peeked in on him after hearing him masturbate in his room, I am sure he has peeked in on me.

As I have mentioned, I have seen and played with Maryann, even spied on the two of them playing in his room, so why not, if it is ok with you. Let's see Kerry how it turns out first then go from there. Ok.

They both finally go up to bed while Kerry goes to her computer to draft and post the ad:

" Male & Female Models wanted, any shape or size -- Must be between 18 years old and 70 years old. Clothing maybe optional -- I am working on a special art, photo & video project. Funds can be provided for your time. Contact Kathy -- e-mail me at (kv) with your contact details, description and photo in shorts and shirt. Note -- I am located in Scarsdale, NY so driving distance to my location is key."

Two days later Kathy & Kerry are in the Master suite's large bed together as usual typically both nude, Kerry looking over her mom's laptop reading and filtering out all the e-mails almost 245 e-mails hit by the 2nd day.

Some they find from school aged 18 year old teens, both male and female including from Kerry's school, containing either a bikini photo or two, or fully nude photo -- one photo they both laughed as they recognized the picture of possible, Jennifer's black BF that popped her cherry, I am a large Afro male, hung like a horse, need the money and would like to Model. Local Contact details etc were provided. In the picture was a black male, and another picture of his penis that was quite large. Both decided to delete the e-mail.

Some others with some more of the girls in her school, some were Kerry's society member friends, and both of them placed them into a save file for potential future models. Kathy sees one that interests her but not Kerry - deleted.

Hello, I am a 75 year old Grandmother, I know you wanted models 70 and under, but I am in great shape for my age, I swim every day to stay in shape, Married with Grandchildren, I don't need the modeling fee money, just want to feel young again. A couple of pictures of the woman was included, one in a bathing suit and Halter top showing about a 38C set of boobs, and another with her dressed in a skirt and blouse, her mixed color silver/black hair in a ponytail. Please e-mail me at (Granny75@xxx) if you want to use me.

After, taking pictures of Mrs. Arnold, Kathy decides this goes into her personal save file for a future modeling session.

Dear person looking for a model. My name is Marylou, I believe I am very cute and adorable; I am 21 years old with long blonde hair that I keep in pigtails or as one long braid; my measurements are 34C -- 32 -- 34. I am a student at Westchester Comm. College, however please catch me before school starts, as I am transferring to Caz College in Upstate NY.

The e-mail continues, my eyes are blue. Nudity -- is fine, as you can see from my pictures and yes, I do keep things down below waxed. I'll even model and would have no issues working with another female or male model. Kathy and Kerry both looked closer at the pictures, enjoying what was sent to them. My e-mail is MLT@xxx.com. Please contact me, thanks.

The first picture was of Marylou, in a basic two-piece bathing suit, not really showing much of anything off, then the next picture -- she removed the top of her bathing suit and finally -- the bottom portion exposing her perfectly, as described, hair less pussy. Her pussy lips, they both noticed, were also quite large but what set off both mother and daughter, were the glasses that she wore, really setting off her beautiful facial features. Mom, let's keep this and please favorite it, she is very sensual looking, Kerry was very much going to favorite it, getting a bit of moisture in her pussy, hoping mom doesn't take notice.

Kerry comes across, the following e-mail and looks at the guys picture then reads the e-mail to her mom. Mom, I think this is the one, are you sure pumpkin, using her pet name, yes, mom, worst comes to worst we stop the session and pay him for his time.

Dear Kathy, my name is Andy Hoffman, I live in Rye within driving distance to your location, I am 45 years old 6 ft and as you can see from my pictures attached, in good shape. I am interested in learning more details. My cell phone is 914-555-xxxx.

Kathy called Andy's phone, with Kerry still in the bed with her, telling him that her name is, Kathy Vanderman, the artist contacting him about the modeling assignment. They chatted for about 30 minutes and Kathy felt safe enough to provide Andy with her home address with the time - 9:00 am and date, next Tuesday to start.

As her mom continues to chat with this guy that may pop her Cherry, it is late, but Kerry heads downstairs to their study, joining Marcus who is watching the evening news on the big screen TV, sitting on their larger couch, as usual also in the nude, Marcus looks over to his sister, still nude, as she is starting to sit on the opposite side of the room on the smaller couch, laughing to himself at her funny tan lines from the spray tan booth, thinking next week, Maryann won't have any tan lines, knowing full well why her mom and sister have grown a little closer the last few days, when Kathy then joins her children, nude as well, she moves Marcus over and sits next to him, as she lowers the TV.

Marcus, Kerry, hi mom they both shout out together in typical twin harmony. Marcus, now you know next week will be a big deal for your sister. I chatted with this guy Andy, he seems nice & also safe, so he will be coming over while you are away with Maryann and her family. I am not sure of the direction it will take, but you are both old enough, to understand that your sister may have sex with this stranger, so she is no longer a virgin going into college, but only if we both approve of him.

You have Maryann and you are not going off to college, your helping me around the studio, & may take some massage classes, I am looking forward to your help and additional input into projects from a younger perspective, so I am not worried too much about you losing your virginity. With that said, I have a gift for you, Kathy takes her hand out from behind her back and hands Marcus a box of a dozen lubricated natural condoms, extra sensitive. Kerry gives out a giggle and says hey we both may get lucky bro next week.

Marcus just hides his embarrassed face and says mom, please. Kathy says, No, please mister, you are going to listen to me. I not sure of the sleeping arrangements, if Maryann is on any birth control and it usually is up to the male, knowing full well about Maryann's possible plans to have intercourse with Marcus, next week as they sleep together.

First, you are going to be very polite and nice for Maryann's parents, yes sir, no ma'am. Second, you are to help with dishes etc. around the villa, third and most importantly, I will give you some Euro dollars that a client paid me with so you can buy them a lunch and a dinner. Meals are expensive, I am sure they will be cooking in the villa but you will treat them out to a couple meals, just like his twin, yes, ma'am. If you sleep with or have an opportunity to have sexual relations you will be nice to Maryann.

You will take it slow, get her warmed up and be very gentle as you enter her, mom TMI, making sure you put on a condom first. I don't need grandchildren at my age! If you do break her hymen, note there will be blood and you will continue, as long as she says it is ok until she has an orgasm. Maybe ask her for a pre-blowjob to take your first load explain that it will be better for her, you are young unlike, your sister's choice, you will recharge quick enough but not as quick as if you didn't cum first.

Hey brother, I know eat her pussy after you cum into the condom, she will like and appreciate that, cuddle with her, and make sure you massage her breasts, they are small but they are very sensitive. As you may already know, smirk, smirk, I have done all that now sis, I just want to finally enter her pussy and have her deflowered so we can continue to add more sexual experiences into our relationship, as we only touch and feel/play with each other.

However, Marcus wonders how his sister is in the know so much about his girlfriend's sensitive small breasts, then laughs to himself remembering the "private" conversation, he listened in on, she had with their mom about the secret club. Remember Marcus, they both say, it is all about Maryann,

Ok ladies, I will try to remember all this, smartly he says, why don't you write it all down on small cue cards, so I can read it as we progress. It would go like this, kiss, kiss, stop Maryann, let me read this card, Mom says XXXX, ok let's continue fooling around, stop, more reading from mom, let's continue Maryann OH, OH Marcus that feels so good, we need to stop, oh wait, I love this one from my sister, he reads, her breasts are very sensitive treat them kindly, massage them then lick & suck on them. Kathy, stands up, along with Kerry and both yell out smart ass, we are going up to bed it is getting very late. GOOD NIGHT.