MaryAnn Loses Her Virginity

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A rite of passage, more fun than a Bat Mitzvah.
4.9k words
4.39
70.8k
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Part 8 of the 15 part series

Updated 09/11/2022
Created 07/04/2007
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Maryann Loses Her Virginity In A Rite Of Passage, Only More Exciting

This might just be the night. By tomorrow morning MaryAnn would be twenty. If things worked out she would no longer be the "last remaining virgin" of the class of '86. Her transformation shouldn't be difficult to pull off. MaryAnn was petite, blond, and beautiful. Her size 32 C breasts atop a small frame stopped conversations when she entered a room. In addition she was intelligent, well read, and talented.

She considered losing her virginity to be akin to a quinceanerafor young, Hispanic girls or a bat mitzvah for young, Jewish ones. It would be a rite of passage. with some major differences. It didn't figure to be quite public, and ought to be a lot more exciting.

Having a sexual rite of passage as late as 20 was unusual, but MaryAnn had a great reason for postponing her deflowering. She had promised her mom, and she didn't take those promises lightly.

Six years earlier she and her mom had one of their woman-to-woman talks. Their talks were was easier than most because the two Flaherty women were always close and always frank. Mom Flaherty, sometimes called Sarah Flaherty, was an archetypical Navy officer's wife. Dad, Flaherty, sometimes called Admiral Flaherty, had graduated from Annapolis and worked hard to become boss of lots of ships plus their captains and crews.

That left Mom to do most of the rearing of their only child, and she did a good job of it. MaryAnn later reflected that it was ironic that her mom had ended up such a liberal thinker after graduating from Stanford, then living as a proper Navy wife. She was a good mother and friend, even from the perspective of a kid.

In the memorable 14-year-old talk, Mom reminded MaryAnn that admirals' kids had to be more circumspect than other kids. Even the word "circumspect" didn't give the youngster pause. MaryAnn had always been expected to use the best word for the occasion. As Mom hoped, and as it happened, words would become her life.

As she prepared for her big night out MaryAnn recalled the earlier talk. Her mom said, "MaryAnn, I realize this is a changing world and you'll have opportunities to do things girls of my generation would not have even thought of. Most of these are great. You want to be a writer and folks are now writing with machines. Computer programs can eliminate much of the drudgery of writing and let you concentrate on being effective.

"I won't go into the old 'when I was your age I used to . . . ' bit. I was not deprived at all and didn't walk uphill both ways to school, but some things were different and you will have harder choices to make.

"To start with I know that most kids your age experiment with sex. The odds are that most will actually do it before they graduate from high school, quite a few before they get to high school. I want to ask you to abstain until you are twenty, even if you have a lot of peer pressure. Let me say you'll be voluntarily giving up something that can be exciting beyond belief. The problem is that in the eyes of everybody, including those who do it, it is wrong. Further it is poorly practiced by kids who have been told all their lives that it is wrong.

It isn't. Likely if we were Tahitians we wouldn't be having this talk, but we're Americans and, for better or worse, we must live as Americans. Please keep all that in mind as you go through your teens."

MaryAnn wasn't surprised that her mother refused make sex a sin or to downplay the enjoyment of it. Her own biggest secret ever was that she once surreptitiously watched her mom and dad doing it. It was also the one that excited her the most.

She was just coming into puberty. Her titties were big enough for a training bra (training for what?). She was growing a bit of pubic hair and her mother had alerted her to menstruation. What she was still lacking was an understanding of what a big deal sexual intercourse was. She got an opportunity to find out one summer in a rustic cabin the Maine woods, one of those places where the rooms were separated by partitions that didn't reach the ceiling. Her mom and dad rented the place to "get away from it all."

MaryAnn had made a friend with a girl in another cabin about a half mile away. One afternoon MaryAnn persuaded her folks to let her spend the whole day at her friend's cabin. She later realized that they would be delighted to spend time in the bedroom without having to be quiet.

As happens often with kids, MaryAnn and her summer friend had a fight, the reason long forgotten. She walked home and came into the cabin. Immediately she heard noises from her folks' bedroom. Not intending to snoop but just wanting to pout MaryAnn went to her own room.

The conversation she heard through the walls was different, even the tone.

"Oh god, Jake touch me there. Yes, yes you magnificent bastard right there."

"You are a beautiful woman, you know that? I want to stick my face in your cunt."

"Yes, oh god yes, lick my cunt then fuck me. Goddamn you fuck me.

Mom had always used the best words for the occasion, but such language! Her dad only cussed when a Democrat was elected, and her mom never cussed although MaryAnn was sure she wanted to do it when someone mentioned Nixon in her presence.

A curious girl like MaryAnn just couldn't resist. She peeked through the cracks and hoped her folks were just too engrossed to look up.

They were. Both were lying on the bed naked, clothes thrown about the room as if they may had been playing at undressing. Now Mommy Sarah Flaherty lay there with her legs spread. Daddy (then) Commander Flaherty grabbed her legs put them over her shoulder and put his face in her crotch. It looked to MaryAnn as if he was going to crawl in.

Then her, staid mother and her professional, no-nonsense, father threshed about the bed having more fun than MaryAnn ever did swimming. Finally the admiral got on top. MaryAnn got the first glimpse of an adult penis. This was of course not only a grown-up dick, it was erect. My god it was huge. She didn't think he could get all that in her mom. It must have been five or six inches long.

But she soon realized if her dad didn't put it in, her mom would chase him down and sit on him. This was the sex she had been wondering about. He not only got it in. She raised her ass and met it on each thrust. Soon they were both grunting, screaming (nobody within half a mile), moaning and groaning, until her dad held her mom tight, gave a few quick strokes and they both lay sill.

The things Mom had left out of her talk on the birds and bees!

Mercifully her folks were not quiet. And that gave MaryAnn a chance to escape. Before she left she heard her mom say, "Jake, let's do it again just as fast as we can. God I love to get fucked by you."

"Did they teach you to talk like that at that West Coast finishing school called Stanford?"

"Up yours sailor. Now get a boner or I'll forget I'm a lady and married to a fucking gentleman.

The things a little girl can learn by eavesdropping! There was probably more but she had to get out of there. MaryAnn slipped out the window and high tailed it back to her friends house. Their tiff would have to wait until she told her friend the exciting thing she'd just seen.

But in the heart-to-heart talk, her mom continued. She paused, took a deep breath, and added, "Please don't think I'm contradicting myself darling, but I am also going to put you on the pill."

"But Mom, you just said you trusted me. " said MaryAnn.

"Of course I do but I also know that you're human. I'd be silly to rely on a lecture to shut off all possibility of your doing what you are biologically urged to do, especially in today's world. If something happens you'll at least be protected from what's likely to be the biggest consequence of that act." Years later MaryAnn gave much the same talk to her own daughter, except that she realized a world that was still changing, and set the age at 18.

The lecture had its effect. MaryAnn made it through junior high without even flirting with the idea of sex. High school was a little tougher. The closest she came was on graduation night when she and Jimbo made out under the pier.

Jimbo was a hunk and exactly the sort of guy MaryAnn should avoid if she wanted to keep her promise. That fall he would be on his way to Notre Dame on a football scholarship. She had been accepted by several of the top schools including her mom's alma mater, Stanford. She passed it up to go to the big school just up the road in Los Angeles.

That afternoon she had marched across the football of a local junior college, wearing the white cap with a gold tassel denoting honor society. Add all that to her looks and she would be a prize for Jimbo if he could capture it.

He certainly tried and MaryAnn did little to stop him for a while. When he kissed her she felt his tongue on her lips and she opened her mouth. Their passion grew as they kissed. He dropped one hand to her breast and fondled it through her blouse, The other went to her butt and he pulled her tight against them. Then he pulled her skirt up, her panties down and fondled her bare ass. God she wanted to go all the way and might have except Jimbo wasn't as sophisticated as he seemed.

Just before MaryAnn lost control, Jimbo did. As the kisses got hotter he pulled her tighter. She felt his erection pressing against her. Almost as if by instinct she moved against it. He muttered, "Oh god. Oh my god. Jesus." He started shaking, then he was quiet.

When they came up on the boardwalk from under the pier MaryAnn pretended she didn't notice the wet spot on his pants. She didn't feel guilty for going so far and she didn't feel virtuous for stopping short of "all the way." But she was looking forward to her twentieth birthday more anticipation than ever.

At the big school up in the big city, she pledged for and joined the journalism sorority, Theta Sigma Phi, lived off campus and had the freedom to do as she wished. Retaining her virginity was perhaps more of a challenge except for three things. She had learned how to defuse a boy's ardor with her hand. MaryAnn lived with the knowledge she was known as "Handjob Mary," but the guys knew they could expect no more than to fondle and her titties and touch her pussy. Within those constraints she was a terrific date.

Her compromise seemed to work for everybody concerned. Once the word was out that "Hand Job Mary" wouldn't fuck but if a guy promised he wouldn't cum in her mouth she would even give a pretty good blow job. In exchange she made sure the guys knew she could be partially undressed but nothing but fingers went to her pussy, then not inside her vagina. Within those strictures some of those guys gave her a thrill equal to what she gave herself.

And she wasn't sure she really missed out on anything. She heard the horror stories from her sorority sisters of what they experienced the first time. All had done it with guys about their own age. Several had told her of how a boy got too excited and got off before even really starting. Tales of wet bellies prevailed. While the idea of sex was still exciting, premature ejaculation by a guy promised to be merely embarrassing and messy.

She amended her plans. When she turned 20 she would try to find a middle aged guy, about 40. She vowed that her first time wouldn't be with a kid her own age. Ever since she had seen her mom and dad going at it when she was a little girl she knew sex could be exciting. Anything that could induce her mom to say "OOOH GOD JAKE FUCK ME HARD" had to be exciting. She looked forward more than ever to the summer vacation following her junior year. Her twentieth birthday was coming up in late July.

As always MaryAnn's free time in San Diego revolved around things Navy. Her dad was still on active duty and based in the town, although he was on temporary duty in Washington at that time. Her high school friend, Jodie, was also a navy brat and had married a sailor.

Jodie invited MaryAnn to a party on July 19th, the day before her birthday. Mac, Jodie's husband was an aviation mechanic attached with a fighter squadron on one of the local aircraft carriers. Jodie told her, "We're having an informal squadron party in a swell beach house. There'll be all sorts of guys there. In fact they asked me to bring along any free chicks I could find. Interested?"

MaryAnn would be twenty at midnight, actually 9 p.m. because she had been born in Norfolk. Of course she was interested. Only one problem: that old decorum bit. Her dad was big boss man of damn near every sailor and officer in the area.

"Uh don't forget who I am. I want to have fun and don't want to embarrass daddy."

"Don't worry about it a bit," said, Jodie. "You'd be surprised at who shows up at these things. They are really very good at not seeing embarrassing things. Anyhow, you are the perpetual virgin. Aren't you?"

"So far," said MaryAnn. "Anyhow I would love to come. Just don't tell anybody who I am. Let me be MaryAnn Jones for the evening."

She dressed appropriately for the party, Her clothes weren't quite as revealing as she wished, considering the plans she was laying. On the other hand they were more practical. Everything could be shed easily if the occasion demanded. She looked in the mirror and unbuttoned her blouse two buttons, smiled, popped a pill in her mouth, and said, "Nite Mom, I'm off to the party."

Her mom said, "Happy birthday darling, have fun, and be careful." Then she gave her a meaningful hug. MaryAnn reflected that it seemed more meaningful than usual. Was her mom also thinking about her birthday and her promise? Was she resigned? regretful? curious?

On the way Jodie and Mac briefed her on the party. The ages would range from late teens to early forties, those in their forties would likely be mid-grade officers or senior enlisted guys. Either would do as long as they were intelligent. She couldn't stand dolts. Navy men would outnumber navy women by about five to one. Counting the civilian guests, virtually all women, there would be a few more men than women, but pretty close to a balance.

The unofficial rules were that anything went as long as both parties agreed. The guys were given to understand that the limits would be set irrevocably by the girls. The organizers were more circumspect than the leaders of the ill fated Tailhook convention in Las Vegas would be a few years down the road.

The party was just getting started when they arrived, a little before nine. Although she didn't usually drink, MaryAnn had a glass of Chablis. It took the edge of her nervousness, and she hoped she would have cause to be nervous tonight.

Right off the bat one of the unaccompanied guys spotted her. "Hey, you came to add a touch of beauty to the joint," he asked?

She felt relieved that it was an older guy. If something happened she wasn't interested in a fumble thumbs dude pawing her. "Beauty is as beauty does," replied MaryAnn. She thought but didn't add, "and for you, you handsome stud, this beauty might do a lot." She sometimes had fun with things she might have said.

They introduced themselves. MaryAnn stayed with her pseudonym of Jones. And her new friend told her his name was Chuck O'Toole. Mr. O'Toole asked Miss Jones to dance, several times in fact, each time a little closer. It was clear they liked each other and MaryAnn was certain he would make a move.

Now the question became how would she respond. Although she was an admiral's daughter she realized she couldn't be too circumspect, given her goals.

But there were limits. After a the third dance Charlie pulled her very tight and brushed his lips across hers. "Please, Charlie, I don't want to make a spectacle of myself. People are looking."

"How's about we take a walk outside. The Pacific is beautiful tonight with the moon, stars, and passing ships. A lovely gal like you would make it perfect. And I'd really like to kiss her."

This was it. The offer. MaryAnn looked him in the eye and replied, "I think I'd love a walk on the beach, and all that goes with it."

Outside she asked him, "What do you do in the squadron?"

"I'm the chief in charge of the jet aircraft maintenance. They call me the fucking master chief, and I can prove that's an apt nickname."

This was the sort of brashness that could have torpedoed the whole thing but it hit MaryAnn's funny bone. She laughed, a real laugh that came from the belly.

She said, "I'll have you know that Mom and my literature prof both insist I use the word that describes the situation best. That was one fucking good answer."

And she knew she had passed another check point on the way to her adventure.

So apparently did Charlie. As they were laughing it seemed natural for him to pull her to him. She turned her face towards him. He kissed her, a nice sweet kiss. Then she felt his tongue on her mouth and opened hers. The sweet kiss became a hot Frenchie. His hands moved down, tentatively, to her ass. She knew she could set stop it right then and there. She didn't. She moved in closer, so close she could feel his erection. She took care to not rub against it. That didn't work well with Jimbo. She wanted to keep Chuck's interest.

He worked his other hand inside her blouse and fondled her titty through her thin bra. Again no resistance. Finally they broke away, "Oh Christ MaryAnn. I wanted to do that the moment I laid eyes on you."

"Anything more," asked MaryAnn. "And be sure to use the words that describe the situation."

"I want to fuck you MaryAnn."

"Chuck, I have something important to say."

Oh hell was this an excuse to get out of it? "What," asked Charles.

"I'm a virgin."

Chuck later reflected that this was the strangest seduction he was ever involved in. "Virgin, at your age? Isn't it time to go past that stage of your life."

Her answer was simple, and complete, "Yes it is. I don't want to still be a virgin tomorrow morning. Like to be involved in the deflowering?"

For a change the 40-year-old chief lost his cool. He missed his opportunity to seal the deal right there with a simple "yes." but he said, "Uh you sure."

MaryAnn covered his mistake. She wasn't going to let this opportunity pass. "Yes, positive. I promised Mom I'd wait until I was twenty. It wasn't easy being the only girl in my group to be so inexperienced, but I did it. Today is my birthday. At midnight I'll be twenty. In fact I am already. I was born in the Naval hospital in Portsmouth and it is three hours ahead of us."

As she talked MaryAnn unbuttoned her blouse all the way. Then she unhooked the clasp on her bra and it fell away. The moonlight glistened off her breasts. She was going for broke, and enjoying every bit of it.

Charles again took her in his arms and again fondled her titties. This time it was skin on skin. She held him tight and slipped her hands under his shirt. This was getting serious.

Finally she took the lead. "Can we go somewhere, a motel maybe?"

"Oh god yes, let's sneak out of here."

Back inside, blouse again buttoned up, MaryAnn, told Josie, "I have a ride home. I'll catch ya later."

"You go girl. Hey, let yourself go and enjoy whatever happens." Then Josie giggled and gave her long-time friend a hug.

Chuck was nervous. Sure he had all sorts of experience, but this was something else. He just couldn't find a motel. MaryAnn took care of that also. Take the Taylor Street ramp off I-8 and you'll find a nice place up there on the left.

After what seemed to be an inordinate period they finally found the motel, and went inside. Now it was his turn to take charge. She had just passed area of her expertise. He took her in the arms, kissed her again, and asked, "Nervous?"

"A little but I've been waiting seventy three hundred and five days for this. Let's make the best of it. Okay?"

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