Sid And Melissa

At eighteen, Melissa was hardly sexually experienced. This was a small college town in a state in which abortion was not legal. A girl of her age couldn't just walk into the family doctor's office and say, "Hey, I really want to fuck! Put me on birth control pills." When she started college in the fall in the big city, she was sure she'd be able to get on the pill.

Her first, "lover", if you could even call him that, had been an upper classman at the university in town. They'd really only had sex once; he'd gotten her drunk. He had used a condom and the stories about condoms breaking and girls getting pregnant terrified her. She hadn't let him do it again. Neither of them had been particularly talented at oral sex. He had used his fingers...and other things on her. She'd let him put his cock in her mouth but she didn't really know what to do and he had become impatient and started fucking her mouth; he had cum and she had gagged and choked and hated the taste and the slimy feel.

Over the summer while her college boy friend Roger was away, she had met Sid. He was cute, and a bit of a bad boy, she thought, or at least very unlike the coat and tie college boys she was used to. He also went to college but not at the same prestigious one her boy friend did. He had been in the Army and now worked for a security, private investigation and bail bonding company while going to school full time. He had stopped to help her when her stupid car broke down. As he worked under the hood, she could not help notice his strongly muscled arms and shoulders. His blond hair was tousled, not plastered down as was the current fashion. He had a cute, tight little ass. He had invited her for coffee after he'd gotten the car started and she had accepted.

She had been prepared for her parents not to like him, since he probably wasn't from a "good family" and was unlikely to ever become a doctor or lawyer. He was actually very well spoken and obviously bright. He just didn't buy into all of the fake airs and show that boys who went to THE university did. He was just Sid, with an easy smile and friendly eyes but an underlying seriousness that said, "don't fuck with me".

To her surprise, her mom and dad had warmed up to Sid quickly. Her dad had served in combat in another war; in a time when most kids were fighting to avoid the draft, Sid had volunteered at seventeen and served in the war as a door gunner on a helicopter. Her dad respected that and appreciated Sid's maturity and his quick wit. She was almost jealous that her dad and Sid had quickly grown to be such good friends. Her mother just thought he was adorable. Melissa was sure that her mother would have fucked Sid given half a chance, in spite of the age difference.

Melissa was quite sure that Sid was very sexually experienced, certainly more so than she was. She had enjoyed making out with him; he had wonderful hands and was an exceptional kisser. He had worked his fingers down there and expertly made her cum. Her boyfriend had never succeeded in that department; she had faked it and he had believed the canard. She would usually finish herself off back in her own bed in her parents' home.

Over a two week period their sexual exploration had become more intense. To her surprise, Sid had not pushed her to fuck. Tonight, she knew she wanted to but also knew she was terrified of getting pregnant. They had reached that stage in their activities where it was time. Her white cotton panties were somewhere, but certainly not where they belonged. For the first time she had chosen not to wear a girdle which provided young women of the time with a difficult to remove barrier. He had made love to her young pussy with his lips and tongue. Melissa had experienced an intense orgasm and then a second smaller one. She would take his cock in her mouth and try to do better than she had in the past. Sid sat back down on the couch in his small apartment. He kissed her softly and she tasted her own steamy little cunt in his mouth. It excited her. Melissa was naked from the waist down. Her furry little pussy glistened in the soft light. She felt delightfully grown up...wanton and sexy, even slutty.

"You're not on the pill, are you Melissa?"

"No?" She replied, almost questioning.

"We can't really go any farther, babe. I'm not crazy about rubbers and they're pretty unreliable anyway. They make a foam, but it's nasty and messy and not much more reliable than condoms...and I hate the taste."

"I'm sorry..."

"Don't be! I understand." He said, and then again began to kiss and fondle her.

She would give him a blow job; she'd let him cum in her mouth, even let him fuck her mouth if he needed to so that he could cum. He had gently repositioned her; he was behind her now, softly stroking her small breasts, removing her blouse and bra. She could feel his hard cock against the cleft of her ass. She wanted to so much...wanted it inside her. And then, his lips were moving down her back as he kissed and nipped his way toward her full, yet firm young ass. He was giving her globes tender love bites.

His tongue was working its way up and down the cleft of her butt cheeks. He was spreading her ass open with his hands, she assumed to gain access again to her plump pussy lips. And then to her shock, his tongue found its intended target and was running in slow circles around the edges of that tight muscle which guarded that dirty place. And then that amazing tongue was inside and she started to move and then, there was a finger in there and then---no! That's awful! It's nasty, I shouldn't allow him to do that...but it feels so good...

"What are you doing!" She almost shouted, pulling away from him.

"Well, I was having a delightful time making love to your cute little ass hole with my mouth."

"You like that?"

"Quite a lot, actually, and since I did notice that your sweet little butt was responding appropriately, so did you."

He wanted to have anal sex with her! Only men did that to each other...strange men. Her hole was very tight and his cock was the biggest one she'd ever...well only the second one, actually, but it was bigger than her boyfriend's was. Her best friend's boyfriend had tried it with her and she had said it hurt a lot and she hated it and it had been messy and gross.

"Have you ever done in that way before, with a girl I mean..."

"Certainly not with a guy, but yes, a few times. First, back in high school; 'teenage birth control' where I grew up. Then there was a girl in Thailand when I was on R&R who introduced me to the finer points. And one other time with another girl who had the same problem you have, she didn't want to get pregnant and wasn't on the pill." He replied, almost clinically.

"But it hurts...it's dirty and messy...its..."

"It can hurt at first, I'm told, less if you are relaxed, you are well lubricated, the guy is patient and let's you get used to it."

"Look, Melissa, it's safe, pregnancy-wise. Most women, again I'm told, will never really get into it. A lot do it to avoid getting pregnant and make their boyfriend happy—at least that was my high school experience. Those that get into it and even prefer it are in a small minority. Girls that end up enjoying it, ah, practice opening themselves up with their fingers and other things. They, ah, clean themselves out back there before trying it, even use an enema. I'm sorry. I was just testing the waters, so to speak."

"Were you going to try to put your prick inside there?"

"Not tonight. You're not ready by a long shot...and maybe you never will be. But be honest, you liked my tongue back there---didn't you?"

"Yes, sort of." She said, embarrassed to admit that she had.

"Hey! It's getting late. I need to get you back home. Here are your panties...unless you want to let me keep them in my hope chest."

"Okay."

"Huh?"

"You can keep them."

Back in her own bed at home, Melissa was pleased that she didn't need the usual finger fuck to get herself off. Sid had handled that issue very nicely. Her ass...he wanted to put it in her dirty little ass. As she thought about it, her fingers drifted there. Without thinking, she soon had two fingers in there. It was just too small and tight. Owe! Damned fingernails. Her hairbrush had a round handle. Shit, that hurts! Lubrication...what to use. She had KY which she occasionally used to insert a tampon when she knew her period was about to start. It was in her medicine cabinet. She coated the handle of the hair brush and tentatively pushed it inside her hole. Oh, gross! It's got shit on it! Oh well, it's my shit and he said maybe an enema...Okay, that's not so bad. But her hairbrush handle was barely half as big around as Sid's cock. Something bigger, she thought. She ran to her bathroom. The shampoo bottle in the shower! It had a slightly tapered shape. More KY...okay, shove it carefully in there. Not bad, not bad...it burned a little and she stopped. It was hardly half way in, certainly not in far enough to stretch her tender little hole as much as it would be stretched by...his cock.

It's so damned full! It's also cold and hard. A cock would feel better there, wouldn't it? It was so nasty. She looked down in amazement as her little shitter stretched obscenely in response to the invasion. She began to move it in and out. Her fingers worked their magic on her little nub. The orgasm snuck up on her and she cried out. Oh, shit, I hope mom and dad didn't hear that!

"Everything okay in there honey?" Her mother called from the door as Melissa quickly hid the evidence of her perversion under the pillow.

"I'm fine, mom, I just stubbed my toe. You can come in, if you like."

Her mother came in, dressed in her traditional floor length flannel gown and sat on the edge of the bed. Melissa's mom was forty six but still by any estimation an attractive woman.

"Did you and Sid have a good time?"

"Sure, mom."

"I really like him. He's not like most of the phonies over at THE university." Her mother paused, trying to collect her thoughts.

"Honey, we need to sit down and have that mother-daughter talk that I know makes you uncomfortable. You're eighteen now, you'll be going off to college in a just a few days."

"Oh mom!"

"Don't oh mom me. Look, I had sex for the first time when I was almost exactly your age. It wasn't anything to write home about and I was scared to death---particularly about getting pregnant. Tomorrow morning after I take your brother to day camp I made an appointment for you with Dr. Caruthers. Things happen and passions flame. I want you to start taking birth control pills---just in case. I wish they'd had them when I was your age! Then again, we found creative ways to deal with things, often discovering that the alternatives could be a hell of a lot of fun."

"Mom, do you and dad still..."

"Oh please! Now I'm going to make you really uncomfortable. Look, you know I don't have periods anymore---so I can't get pregnant. No more messy jelly and uncomfortable diaphragms, no pill that make me fat, no inconvenient times of the month. You dad and I fuck more now than we did when we were your age. And without the fear factor of an unwanted pregnancy, it's more fun than ever." Her mother paused. "Have you?"

She could not remember ever hearing her mother say, fuck. "Yes and no. Once with Roger, with a rubber, I was scared to death, he came almost immediately...it wasn't very good."

"I'm sorry hon, but just for the record, my first time was every bit as dismal. It wasn't until I met your dad that I found out what it was supposed to be like---and I've been addicted ever since."

"Before the pill, how did you keep from getting..."

Her mother's boldness shocked Melissa. "I learned to suck cock. I owe your dad for that one. I was totally incompetent the first time or two but he was patient and I came to enjoy it a great deal---still do!"

And then to her further surprise, Melissa's mom gave her daughter a short dissertation on the finer points of exceptional cock sucking.

"And then, of course, Melissa, your pussy and mouth are not the only places that a nice prick can find a happy home in." Her mother said, almost lasciviously.

"You and dad..."

"My first and only—and at least once a week to this day! It's real useful when you have your period. At first, I didn't love it but I didn't hate it either. Again, your dad was very patient. By the time I was twenty, I had grown to enjoy being boned up the shitter more than I might have admitted at the time. Now that I'm post menopausal, we usually have to use a little lube anyway, even the regular way. You father usually lubes both my holes and we just go whichever way strikes our fancy...usually both, cunt first, then my butt. And then of course there is your father's talented tongue...Have you done it that way, yet?"

"No, but I..."

"Want to try it?"

"I guess."

"Practice, cleanliness, the right lube and the right man." Her mother said and then gave Melissa more specific guidance.

Melissa said goodnight to her mother and gave her a big hug. "Thanks mom, you're the greatest."

The next day the two women visited the family doctor. Melissa left with her first little round tray of pills---pills that Dr. Caruthers warned her would not be effective for at least a week. While waiting for the prescription at the drug store, Melissa's mother also picked up a dozen disposable enemas. "Half for you, half for me." Her mom said with a twinkle in her eye.

To her further surprise, Melissa's mom made one more stop on the way home, parking in front of a sleazy looking store that obviously sold items of erotic interest. Melissa was further shocked when she discovered that her mother and the woman who owned the store were obviously on a first name basis. Melissa had no idea what such stores sold. A half an hour later she left with an ample sampling of their wares.

Her mother had selected an anal lube, her favorite and in fact had ended up getting a bottle for each of them. Melissa now owned her first official vibrator. She also possessed an instructional manual, entitled simply, "Sucking Cock". The piece de la resistance was a small wooden box containing an assortment of ever larger butt plugs.

"I have that same set, Melissa, well actually I also have a larger set. Sometimes I'll shove the biggest one up my ass---well lubed, of course---and go visit your father at his law office wearing a loose skirt and no panties. I'll just wink at his secretary as I breeze by---hell she knows damned well what's going on. I'll put one foot up on his desk and shake my fanny in his face. He'll work that bugger in and out for a while and then use his tongue. Then he'll just butt fuck me like some crazed animal until we both cum. Then the delightfully dirty bastard will suck his own cum out of my little shitter. The first time a man shoots his cream in your rectum, you're going to come unglued, baby. He likes me to play with and lick his ass too. As a matter of fact I've got a strap-on now, and sometimes...oops! Too much information!"

"Mom, is there anything you and dad..."

"Don't do? Yea, were not into scat or golden showers. Oh, well piss on each other in the shower---we still shower together in case you hadn't noticed but we don't drink it. A little mild bondage is fun and a little spanky, nothing approaching real BDSM. We've never had any desire to swing or bring other couples in to the scene. We have taken vacations at clothing optional beaches and still love doing it outside. A couple of times, we have brought another woman home. It excites your dad to watch another woman eat me---and vice versa. And I have to admit that watching your dad bone some little bitch---we tend to go for younger women, not much older than you are---gets me off. I know he's never cheated on me, nor have I on him. We're best friends and love each other to death; we have no secrets. Our sex life is very intense and the excitement has kept both of us from even thinking of straying for a very long time."

"What do you think of Sid, mom?"

"I like him a lot and not just because he is cute! He probably isn't going to end up being a doctor or lawyer, but he'll do just fine in life. Did you know that your dad hired him, or more accurately, his firm, to do some investigative work for one of his clients? You know how picky your dad can be. He'd been looking for a new PI since his former one, a very old friend, had a stroke and had to retire. First, your dad told me that Sid's firm did exceptional work: on time, discreet and thorough."

"He went down to their office to pay them and met the senior partner, a retired military guy. Well, it turns out that Sid doesn't exactly work for the firm, he's a partner with an ownership position. The senior partner retired from the Army and took the business over from his uncle who had decided to retire. Sid served with him, 'over there' and there is a definite bond between the two men, almost father-son, but something more. You know your dad, he and the senior partner struck up a friendship and ended up going to lunch together."

"You've seen your dad in court questioning a witness, so as you would expect, he probed. It turns out that Sid and the senior partner got shot down together in the same helicopter. They hit nose first and the two pilots were killed on impact. They rolled over and the crew chief was crushed to death. The senior partner, Mike Sampson, I believe, was a Major riding in the back on a command and control mission. He had a broken leg---compound fracture---and a punctured lung. Sid was pretty beat up but had escaped serious injury. Every attempt to get in and extract them was forced back by enemy fire. Nightfall came. So, Sid patched up Mike Sampson as well as he could, threw him over his shoulder and escaped and evaded through ten miles of jungle, finally getting to a safe extraction point two days later. The Major, Mike, put him in for the Medal of Honor. It was downgraded to a Distinguished Service Cross, the second highest award you can get. When Sampson got out of the hospital, they retired him on disability. He tracked Sid down and convinced him to move here. Sid enrolled in college and Mike offered him a partnership. Your dad now uses their firm for all of his work, including bail bonding."

"Look, Sid's got some rough edges and he works in an industry that can be pretty nasty. He's a tough kid that didn't grow up with much and spent some time on the mean streets. He's what, twenty-three? He's got a good job, he's a business owner from heaven's sake; he'll get his degree because it's important to him. He knows how to take care of himself, and while you're far too young to even be thinking about marriage, whatever happens when you go off to college, stay in contact with him."

Melissa's mom was almost done. "A long time ago when I thought I was some kind of debutante---well, actually, I was---I was sitting in a bar in NYC one night after attending one more meaningless society party with one more, living-off-daddy's-money, drunken date, when a young soldier, just back from the war, still in uniform with a chest full of medals walked in. The assholes I was with---fucking draft dodgers, every one of them, made jokes—loud enough that he couldn't help but here. All he did was smile, tell the bartender to buy our table a round and then ignore us. I went over to thank him, to the derision of my companions. When I looked into those deep blue, sad eyes, it was all over. My little pussy was dripping! Bluntly, I dragged him to a hotel across the street and fucked his brains out....and continued to do so for the next three days. And that's how I met your daddy. We got married two years later as he was finishing up college and getting ready for law school. My parents almost disowned me but finally came around. Today they love him to death."