Another Cherry

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Coed and her favorite uncle.
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Momstheboss
Momstheboss
3,101 Followers

I looked over my wife's shoulder looking at the picture that she was studying. We were at the annual Memorial Day gathering of her family.

"Who is that?" I asked.

"That is Rachel." Her mother said proudly from across the table.

I turned to look at the 23-year-old Rachel standing halfway across the kitchen. "You clean up real good girl!" I said, causing her to smile shyly.

The picture was stunning! Her blemishes and slight acme covered up, her hair combed perfectly and falling over her shoulder and face on one side, created a portrait of a very lovely young woman.

At 45, I had watched the girl grow into adulthood. I did not even know her age until just recently, surprising me that so much time had slipped by. I now began to study the girl with more interest. Having bedded two of my wife's sisters, I wondered if it was possible to bed such a young girl, a niece. I checked it off as a foolish thought, but it did not prevent me from appraising her womanly attributes.

In my opinion and liking, she was lacking in almost every region. She was a bit taller than my 5'9". Wearing a black, wraparound skirt and a silky deep red tapered blouse, her breasts were almost nonexistent. A slight protrusion, yes, but she was a girl one might call flat-chested. Still I wondered what they might look like. I found her thin hips quite appealing and watched her slight sway as she moved around the kitchen. Her legs were not at all pretty but shapely. I knew it was quite possible that the blemishes disappeared halfway up her thighs. I hope they did, anyway.

I knew she had just broken up with her latest boyfriend. My wife had told me the story and it was not pretty. Rachel's boyfriend of two years showed his true nature by suggesting they watch X-rated videos with one of his male friends.

Rachel was well bred and I knew her moral standards came from the older female clan. It was not a surprise that she had dumped the guy. Though the girl needed a few hamburgers to fill out her body, she would no doubt one day make a fine wife. But, I knew pickings were slim on the Eastern Shore of Virginia for a young girl of Rachel's raising. I hope she'd have enough sense to leave one day.

As with all of my wife's family and offspring, I had showed interest in their lives and the things they were interested in. I spent many an hour playing on a Commodore 64 with the boys and teasing the girls. Rachel was no exception and I always asked her about her life in general and what she was doing. I eventually found her alone, as one can be in a house full of people, near the opened front door that looked out upon a big yard and vast field. The storm door was the full glass type.

"How have you been doing Rachel?" I asked walking up behind her. "I hear you're working at the community college.

"Yes. I like it a lot but I'm looking at a few colleges." She answered. "I have not finished my degree yet."

"Where do you want to go?" I queried.

"Salisbury is the closest but I want to get further away, perhaps, Buffalo or New Hampshire, near to Judy." She replied.

"I highly recommend the mountain country of New Hampshire. It's a whole different world compared to this flat country, and Judy has a big house should you visit."

"She's a bit high strung for me but I guess I would visit occasionally." She said with a slight smile. "Staying close to family would make my mother feel better."

"I know what you mean." I said, smiling back. "That's why I didn't say, if you stay with her."

"I would miss a view like this!" She said.

I turned to answer a call from my wife and returned to the kitchen. At the end of the gathering, I sought Rachel out and gave her a hug, telling her to take care in whatever she decided to do. The weeks rolled by. I saw Rachel a number of times during the summer when we visited one house or the other of Della's sisters.

In late August, my wife said she had talked to Rachel's mother and was hoping that I would consider driving Rachel to New Hampshire. It would not be the first time I had shuttled my wife's family members to and from the Northeast. I agreed and the plans were finalized. In early September, before daybreak on a Saturday morning I headed for the Eastern Shore in my truck to gather up Rachel and her few suitcases etc.

"So, Miss Rachel, are you excited about school and getting away from home?" I asked as we turned on 13 N.

"I'm scared to death." She replied, with her shy tone.

"Well, you just settled back and relax. We'll have you at college in about 13 hours."

"Are we going to drive straight through?" She asked with a bit of concern.

"That's one part of the trip that wasn't discussed." I replied. "I've always been used to doing long drives. But it doesn't have to be straight through. We could stop in the City if you like?"

"Could we?" She asked excitedly. "I saw New York City back in high school, but you used to live up there, didn't you? You could show me some neat places I bet?"

"I used to live on Long Island." I told her. "But yes, I could show you a few neat places. We could stay in one of the big hotels in the city. One last fling before you have to settle down and hit the books."

She was beaming as I reached for the cell-phone to call my wife to tell her of the plans. She expressed a bit of concern about the expense of two rooms in the City, but agreed it would make Rachel happy. She agreed to call Rachel's mother.

My wife had mentioned, with emphasis, the expense of two rooms, which made me a bit tense. Was it possible she knew are suspected something about her sisters? But I'm a conspiracy nut anyway so I pushed it to the back of my mind.

For whatever reason, Rachel scooted a bit closer to me on the bench seat of my truck. The concerns I had had about riding such a long way with such a young girl, that actually, I didn't really know, I put to rest as I listened to her near constant chatter. She commented about the scenery, the traffic, the leaves falling from the trees and anything else an excited young girl raised on the Eastern Shore could comment about.

"Did you eat any breakfast?" I asked as we rolled into Newcastle. "I ate some cereal, but I'm starving, how about you?"

I pulled into a buffet restaurant. Rachel hugged my right arm as we walked across the parking lot to the restaurant. I'd never seen anyone eat like she did. It may be happy to think I was helping to put pounds on the slim young lass. She again hugged my arm as we left the restaurant and I opened the passenger side door for her, making her smile as she said, "thank you good sir!"

We hit the Jersey Turnpike with Rachel sitting "very" close to me. As I sped through the toll plaza she kissed me on the cheek.

"Thank you for lunch. I'm so excited about staying in the City tonight!" She exclaimed. "I wished I had brought something nice to wear."

"What would your mother have to say about that?" I quizzed.

"Don't be a killjoy." She said, tapping me lightly on the leg.

She chattered for many long miles before she became quiet for many more long miles. I glanced at her, saw her eyes open, and wondered why she was so quiet.

"Rachel, are you okay?" I queried softly.

"No, not really." She answered, dropping her head onto my shoulder. "Do you think it's weird for a 24-year-old woman to be a virgin?"

It took me a few moments to recover.

"I suppose, we're talking about you?"

"I came really close with, using your favorite word, that lowlife I wasted my last two years with, but when he touched me - down there - I came to my senses." She confessed. "I hate being a virgin. I just want it to be with someone I care about, a lot."

"I have to say that it's unusual for a girl your age to be a virgin nowadays, but I know your grandmother, rest her soul, your mother and the other women in your life. Your aunt was a virgin at 21 when I married her. Kate and Judy might have strayed from the straight and narrow before they married, but the rest of the girls I would bet money were virgins when they married, all in their 20s." I related. "And I certainly commend you."

"You seem to know a lot about the sisters?" She said.

"Things get around. Stories are told." I replied.

Again, Rachel became quiet for a few miles.

"I would not mind giving you my virginity." She said, placing her head on my shoulder again. "I know you are kind and would be gentle. Mom has never broached the subject. I've been scared to. I've read so much and it's scary."

"I'm flattered Rachel, but you need to forget that foolishness." I began, trying to keep my mind from screaming "another cherry". "You really hardly know me. You see me mostly on holidays. You need to spend time with a person before you give yourself away." Continuing in a few moments, "we're having a good time, we're going to spend the night in the City, have a good meal and stay in a nice hotel. It must feel like a fairytale to you but it's far from it. Us being intimate could have serious consequences."

"You read stories all the time about young boys having a brief affair with an older woman that they remember for the rest of their lives." She defended. "What's wrong with a young girl giving an older man her virginity, someone she will remember forever. You sure as well will!" She added, with a chuckle.

"Like I said young lady, you need to rethink this." I cautioned her. "Now get ready! We're coming out of the tunnel and it's a beautiful crisp day. Say hello to New York City!"

Rachel was like a child seeing a parade or Santa Claus for the first time. She literally bounced on the seat, hugging my arm. I drove us around the city for an hour and a half pointing out various things I thought would interest her. A slow drive, whether you wanted to or not, down Broadway, then, Central Park topped it off before we headed for the hotel, hoping they would have a room for us high above the city. Not really worried, as five-star, expensive hotels will always have a room. It was almost dark.

I pulled up in front of the Waldorf-Astoria and exited quickly, turning the car keys over to an attendant. Our bags would eventually turn up in the room. Air-miles and a small amount of real money would fund the one $500 room. Yes, I said, one room. We were underdressed for such a hotel, but brashness speaks of money, and I had a lady to impress. Borrowing a tie at the Peacock Alley Restaurant would be a minor inconvenience.

I rationalized the one room idea to Rachel, explaining there were cheaper hotels but I thought I would give her a real treat. She readily agreed, not inquiring as to the number of beds in the room. I went out of my way to inform her there were two beds. Requesting high, Rachel was wowed appropriately by the luxury of the room on the 46th floor and spent many minutes roaming around looking and turning on lights. She returned to a window often.

After a very good dinner, we made our way by cab to the Empire State Building, riding on a number of elevators to the top. I was always awed by the night view of the City. Rachel seemed overwhelmed as I followed her around trying to keep up.

After we had arrived in the City there had been no more talk of virginity. But, all the while I was pondering the outcome of this day. My every fiber told me to reject the offer. But I knew deep down it wasn't in me to do that. I had fucked two of my wife's sisters. What really frightened me was having the same problem with Rachel as I had had with my wife. After chasing my wife's ass all over the bed on our wedding night, finally calling it quits, it took weeks for me to finally get my cock in her fully. We did not have comfortable sex, for her, until after our first baby was born. If I ran into the same problem with Rachel, I just didn't want to think about it, it would be a disaster for her.

We finally returned to the hotel room and Rachel became awed all over again. It was near midnight. Our specified two suitcases were there. I told her I was going to take a shower. I showered and came out with only a housecoat on and told her the bathroom was hers. I did not see the clothing she retrieved from her one suitcase, but I fully expected her to return wearing a housecoat. She did not! I was sitting on the leather sofa drinking a Coke and watching the weather when Rachel exited the bathroom.

She approached me wearing a very thin, thigh length, light-blue gown. I could clearly see the white panties through the nightgown. They were of the bikini type. Also, the size and shape of her breasts were no longer a question. They were indeed small, maybe a handful, just.

"Do you like?" She queried turning in a circle.

"More than you know." I answered. "But I thought maybe you had come to your senses?"

"I know you don't believe me but I have thought long and hard about this. There is no worry of pregnancy and I know you're not going to turn me down."

"And how have you become so wise?" I asked, a bit of surprise in my tone.

"I hear things too!" She replied with confidence. "I overheard Judy and Katie talking months ago. Don't worry uncle Bill, your secrets will not be revealed by me."

I figured there was no need to deny anything. She continued.

"Katie I can see. Her husband is a lowlife. But how did you get high strung Judy into bed?" Rachel queried. "I miss Katie a lot. We were close. Was she able to -- you know?"

"Della had left for work. Judy called me into the bedroom where she was lying naked. Surprised the hell out of me too." I explained. "I miss Kate too. And, yes, she did quite well."

There were a few moments of uncomfortable silence.

"I hate to admit it but I am a bit embarrassed for you to see me naked." She said, turning and walking toward the beds, the thin nightgown giving me an excellent view of her buttocks. "So would you turn off all the lights? I would like to leave the curtains open to let in the lights of the city."

Reaching the beds, she turned, waiting.

"So you're not going to listen to reason?" I asked.

"No."

I think Rachel had cut on every light in the room again. I counted eight including the bathroom lights. Rachel was in the bed on the right, a large queen-size luxurious bed, and had positioned herself on the right, under the covers. As I removed by housecoat and entered the bed, I doubted if she could see my already quite rigid erection. She turned to face me and snuggled in close. I stayed on my back.

"This is such a lovely place to lose my virginity." She whispered in my ear. "And I know I'm with someone I can trust and care about."

Someone she could trust? I was probably going to feel like a heel after taking this young girl's virginity, but in the end it would be something of joy to me. I was going to do my best to make sure she would feel the same way. I turned towards her, taking care not to let my erection poke her, gathered her in my arms, and kissed her. A long tender kiss turned passionate as I slipped my hand under the gown to cup her breast. She pushed her tongue into my mouth when I thumbed her nipple. It became firm under my touch.

"Can I touch it?" She whispered, breaking our kiss.

"Of course." I answered.

I felt Rachel's hand touch my belly and proceed down until she found my cock. Her fingers roamed up and down the shaft a number of times, then, toyed with the domed head.

"It's so hard and big."

"How about we removed the nightgown." I suggested.

In the darkness I watched her ultra-thin form lift up and remove the nightgown over her head as I stripped the covers off us. When she came back to me, my right hand immediately went to her butt and I squeezed it tenderly as I pulled her against me, ignoring my erection rubbing against her belly as I slipped my knee between her legs bringing my knee tight against her crotch. Her slight gasp was as expected, as was her, seemingly involuntary, left hand reacquiring my cock. Except, this time there was no toying, she gripped it firmly.

"I want you in me!" She exclaimed in a whisper.

"Shhhhhhhhh." I breathed in a calming tone. "This is only going to happen once so lets take our time and make it last."

We began to kiss passionately again, our tongues fencing. My hand explored her body for many long minutes before I slipped it between her legs, replacing my knee. With my middle finger extended, I tenderly pushed her panties against her labia, then, creasing it between the length of the lips. Her moans vibrated against my face as she yanked on my cock. Her panties became wet. With Della, only on rare occasions did I get to experience the wanton exhilaration of a woman in lust. I slipped my finger under the crotch of her panties and another burst of sexual desire shot through Rachel's body.

I was touching her "there" and she did not shy. It eased my conscience just a bit knowing she was welcoming my touch to her treasure. Yes indeed, I considered her young pussy a real treasure. It was soft as cotton. I left her pussy momentarily to strip her of her panties. I had yet to seriously concentrate on her clit. When I put my finger to her clit, her back arched as our kiss broke and she groaned a most passionate groan of animal lust. I began to scrub her clit with two fingers, causing her to lift her ass and widen her thighs.

"Please, Bill, take it now! " She begged. "I need your dick in me."

I had no intention of stopping, fulfilling her plea. I wanted her to be sopping wet when the time finally came. Knowing, the more lubrication the better. My wife and I had early on used Vaseline often. And, there was one other thing I needed for me.

I started at her breasts, suckling on each nipple for a long moment before moving down her belly. A few minutes earlier, as my hand slipped between her legs, her bush had felt ample enough. Now, as my nose eased through it I deemed it to my liking. I pushed her legs wide.

"Are you going to kiss it?" She whispered.

"Do you mind?"

"Heavens no. I was hoping you would. I've read so much...............

Her knees naturally bent and lifted as I pushed my hands under her buttocks.

"Oh God!" She moaned when my tongue touched her clit.

I breathed in deeply to imprint her feminine odor on my brain. This was going to be a delicate venture. I did not want her to come, but to be at the very peak of wanton desire. I teased and taunted her clit until her mutterings and moans seemed delirious. She was now indeed sopping wet, my face and chin attesting to it.

"It's time Rachel. Relax as best you can and guide it in." I said lovingly as I moved to mount her, taking care to keep my weight off of her.

Rachel reacted quite naturally as she acquired my cock and placed it to her. I pushed into her very slowly as her body stilled under me and seemed to tense.

"Relax sugar." I coached. "Let your body relax and most of all let your pussy relax."

"I'm trying to." Her voice trembled in reply. "I wasn't expecting it to be so big."

I planned on telling her later that I wasn't all that big - 6 inches at best - but thick - and there were bigger out there.

"I know." I whispered lovingly. "We're almost there."

She whimpered slightly and it was done. I was fully into her. I pushed deeper causing her to gasp, then:

"Is that it?" She queried with surprise.

"That's it Rachel." I assured her. "Not that bad after all. Now, we'll go easy and break it in a little. If you feel so inclined, push back when you feel comfortable. But tell me if you begin to hurt."

"Break in my pussy! That's funny Bill." She giggled.

I began to pump into her slowly. After a few moments she began to push back.

"That feels real good!" She said. "Can we go a little faster?"

"We can do anything you want. Just tell me what you desire." I replied, as I began to pick up the rhythm.

"Where do I put my legs for best penetration?" She queried.

"Unwrap them from around me." I directed. "Pull them back as far as you can and keep them as wide as you can. You're moving your ass just fine. It's very arousing."

Momstheboss
Momstheboss
3,101 Followers