My Sister's Cherry

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Helping her to lose her virginity.
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Kat900
Kat900
25 Followers

I came to home to visit the family for a days before starting my first full time job after college with a freshly minted MBA. My little sister had just graduated from high school and was accepted for the same small college that I went to. The folks were off to a shindig 100 miles down the coast and wouldn't be back until the next day. This was a prime sister bonding opportunity. We'd always been close but our 5 year age difference strained our relationship somewhat but now she's 18 and a legal adult. I couldn't wait to find out if she was sexually active. Our family wasn't at all uptight and we often skinny dipped in the back yard pool together I'd wanted to talk to her about my sexcapades then but she was too young for that. I'd gotten a reputation of being a fast and easy lay in the dorms which didn't bother me and now I just chock it up to my exploration period. After a light breakfast we sat on the couch sipping coffee and I jumped right into it.

"So Vicky, are you dating anyone."

"Yea, this guy Danny and I have gone out a few times."

"Gone out with as in 'Gone Out' with?"

"Just movies and burgers for the most part. We did go to the beach last week."

"That's a good place to start something. Have you done anything romantic with him?"

"Not much, we hug and kiss when he brings me home, but I'm afraid to go too far with him and he's very shy. I'm pretty sure that he's a virgin too."

"Come on little sister, haven't you played your V-card yet?"

"I've been on the pill for two months but so far it's just me and some toys."

"Do you have your own or use Moms"

"She has a variety in her night stand."

"Yes I know and last year she admitted that she left them there for us to find."

"So which one's your favorite?"

"The little one, I don't want to pop my cherry that way but it does feel nice humming away. I can feel it stretching my hymen a little. Which one do you like?"

"Well like you I started small and worked my way up. Now I have my own collection. Wait here, I'll be right back."

I went to my room which was now the guest room since I'd left for school. Digging through my bag I'd only brought one for some tension relief and didn't expect to get any live action during this visit. It was a soft fat long one a bit over size with no vibrator. I'd used it last night while remembering that guy last summer that was well hung. It was a realistic replica with veins and a small hole in the tip of it's mushroom head. It had an unrealistic sac at the base that felt good slapping my perineum when I took it deep. My head started to tingle as I stood there caressing it and considered giving it a lick but Vicky was waiting in the living room.

"This is my go to toy when I'm turned on and there's no guy available."

"I looks pretty big, it that the size of the average guy?"

"Some men are that big but most of them are a bit less endowed. We've both seen Daddy's when he's flaccid and I came home early from classes one afternoon as Mom was sucking him off on the couch. I'd say he's about average, how big is Danny boy?"

"I'm not sure, at the beach last week we were laying in dunes and kissing and playing with each others tongues which got me hot. He got brave and put his hand on my boob over my bikini top so I pulled it up to give him direct access. This went on for a while and I put my hand down his shorts and held his cock.

"How did that feel?"

"Interesting, he was very hard and longer then my hand could cover. Anyway I was pulling on him to see what would happen when a couple of fishermen came walking down the beach pointed at us and laughed. I quickly pulled my hand out to his shorts and yanked down my bra. We were both embarrassed and we left the beach post haste."

"So your opportunity passed that day. Has there been any other moments in time since?"

"No but that was just 2 days ago. He called the next day apologizing profusely for what happened but I told him to stop it and we had done nothing wrong and that it was normal."

"There will be more times like that in your life. Actually more then you imagine right now. Was that the only time you touched a guy?"

"Yea but can I hold your toy?"

"Sure, it's a good visual aid except the nut sack. A live one hangs down more freely."

"I've seen Dads. Does it grow or anything when he get a boner?"

"No, for most part it's just hangs there. Guys like for them to be played with and they really like to have them sucked."

"Can I try it here with this one?"

"Be gentle and never use your teeth on anything down there."

She held and stroked it for a bit then took the head into her mouth and held the sack.

"Now massage the balls and lick the underside and stick your tongue in the hole but be careful when you do that with Danny boy. Their urethra is very sensitive and guys usually don't like too much of that. A trick to try is to lick right underneath at the base of the head. There's a bunch of nerve ending there and you can actually get him off that way. Be aware that when he cums that way you'll get a face full of his spunk which I enjoy. It's like a warm lotion and sometimes it tastes good, all guys taste different. You'll need to clean it off eventually because it's sticky but in the meantime the scent's a turn on."

"Well that's interesting, I'd like to do it with a real one."

"Don't do it unless he's gone down on you first. Guys like it a lot and I like to play with it when they com on my tits. It's warm and slippery the smell is weird in a nice way the same as your juice does. A penis is a marvelous thing for recreation, elimination and recreation all in one package. If you're lucky he'll know how to run the head on your clit. That's especially nice when he does it from behind."

"I'm hopping that I wont have to wait much longer."

"With your perky tits and tight little ass I'm amazed that you haven't already. Would you like me to break in Danny boy for you?"

"If you even try I'll cut all your tits off while your asleep."

"Just kidding sweetie, let's get in the spa"

We went to get undressed and grabbed towels. Her breasts had grown to a nice B cup with small areolas like mine and her clitoral hood was peeking over the top of her outer lips. I was starting to feel aroused and shaming myself for it. She's my sister after all. I grabbed her foot and massaged it working my way up her leg. Just as my hands got near her crotch the doorbell rang. She wrapped a towel around her and went to answer it. When she returned she had a boy by the hand.

"Beverly this is Dan,"

I was dumbfounded sitting naked in the spa and moved my arm to cover my breasts.

"Would like to join us Dan?"

He stammered and we exchanged greetings. Vicky whipped off her towel and got back in the water. Dan just stood there like a deer in the headlights.

"Come on Dan, we won't bite"

He nodded and pulled off his shirt and shorts then finally his briefs. His sizable limp penis dangled from his furry crotch and his nut sack bounced as he quickly got in the water. We chatted idly but he couldn't keep his eyes off our boobs, no surprise about that. So there we sat with Dan and Vicky naked together which was surreal and exciting. I could tell that Vicky was getting excited as her nipples grew out and obviously hard. I'd been to nude beaches but this was something different with two virgins that were on the verge of getting it on.

"I'm getting lizard skin, let's gone inside."

I wrapped my towel around my waist to see what Danny boy's reaction would be to my bare boobs. Vicky did a full wrap and Dan held his towel in front of his crotch. We sat on the couch with Dan between us I noticed that I'd left the dildo on the coffee table.

"So Danny are you still a virgin?"

He actually blushed and said "Does it show?"

"There are some clues like you hesitated getting naked with us and your pubes aren't trimmed."

"Does that matter?"

"Not so much to most girls but the hair holds sweat and can smell bad if it isn't clean. When you take a condom off doesn't it catch your hair?"

"I've seen pictures and videos and wondered about that."

"Would you like us to help you do that?"

Vicky was wiggling on the other end of the couch and spread her feet apart on the table.

She looked nervous and was obviously excited. He didn't say anything but I knew he liked the idea.

"Vicky go get the clippers and let's give this boy some grooming."

She dashed for the bathroom and came back with the clipper, a razor, shave cream, lotion and wash cloth. We pushed the coffee table up against the couch and spread the towels out for him to lay on. He scooted out to be nearly fully reclined and we went to work. The clippers first as Vicky held his dick to the side and cut as much hair off as possible. I just hung back an watched to give Vicky this opportunity to play with him. She and I had been doing our own primping for years so she knew pretty much what to do. As she lathered up his cock it got hard of course and she expertly shaved his crotch completely bald. She'd lost her towel somewhere during all that and I pulled mine open. When I thought they weren't looking my way I gave my pussy a few strokes then licked the juice off my fingers. After she wiped off the shave cream and toweled him dry she took some lotion in her hands, dribbled some on his hard dick and rubbed it in. This had me near an orgasm just watching them.

"You missed a spot Vicky. Remember what we talked about earlier. Let me do this part."

I put a large dollop of lotion in my hand and rubbed it into his balls. This made me so hot that I couldn't help but continue on to his hard shaft for a few strokes and played with that special spot under the big purple crown. Vicky had one hand on her tit and the other between her legs. I took her hand and put it on his cock, put his on my pussy and mine on her vulva and fingering her clit. It wasn't long before we all had an orgasm at nearly the same time. To his credit and my joy he remained hard as Vicky kept stroking him.

"OK you two it's time for the main event. Lets go to the big bedroom. I'll get the camera out and give you a record of it. Don't worry, I wont make a peep and let you explore this beautiful occasion."

We got up and she led him by his dong to the king size bed in Mom and Dads room. I pulled down the covers and they climbed onto the sheets which looked very clean. The camera was on the dresser and I watched them kissing and fondling each other all the time recording. It was so beautiful to see this happening and my pussy was dripping. The picture jiggled a bit because I was fingering myself wishing that I'd brought the dildo with me. My fingers played with my clit and found their way into my vagina as deep as I could make them go.

He played with her nipples and sucked them to extended hardness. The lad had class and got between her legs and worked his mouth onto her clit and labia. She got a strained look which I took for an orgasm. It was just so beautiful to watch this and she pulled his head to kiss him as she reached down to grab his penis guiding it to her opening. I zoomed in to get the moment of him entering her. Somehow he knew to go slow pulling back an trusting again then finally he was all the way balls deep in her and stopped as she got used to the intrusion for the first time in her life. As she relaxed and smiled at him he slowly thrusting in and out and she was obviously enjoying the feeling. She had an orgasm and bucked. Predictably he fell out and put his very nice size cock back into her more easily then the first time. She moved with him until he came and they stayed connected in a blissful loving embrace. I turned off the camera and silently went back to the couch, grabbing the dildo and gave myself 3 orgasms. The intoxicating odor of our juices was still lingered from our hand jobs earlier. It was so exciting and I hoped that a threesome was in our near future.

Kat900
Kat900
25 Followers
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AnonymousAnonymousover 6 years ago
Total load of crap her bother

Should have just pushed is cock in as deep as it would go and shot his cum deep up inside her unprotected pussy.

Spoiled by the crap about the pill

This is story land no VD or babies

prop69prop69over 6 years ago
Not much. I thought it would be a brother/sister story

Very boring. Should have been in another category. Either bring Dad in or find a long lost brother to pop her cherry

AnonymousAnonymousover 6 years ago
Incest?

I guess I missed it. This should have been in the Exhibitionist section. Not very interesting over all.

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