Jimmy's First Time

During her senior year, three months after her eighteenth birthday, Mary found herself and her cheer leading team mates Ann and Jane goofing around in the locker room snapping each other with towels when Lynn, a renegade among the group, came in from the shower with her big "D" cup tits bouncing for all to see and admire. She plopped down on the bench right across from them with her legs spread wide so they could see she was shaved clean. This was the 60's and girls didn't shave their pussies. They wore a full bush as a badge of honor showing they had developed into a woman. Another thing girls didn't do was talk about having sex. They were supposed to be demure and virtuous. If they had sex they kept it to themselves and hoped their lovers would be discreet enough to do the same. Not Lynn! She bragged about having had this guy or that guy, the size of their peckers, what all they had done and where they did it. Some of these escapades were tantalizing but most of them just sounded gross. She talked about sucking guy's cocks, licking their balls, riming them and being fucked in the ass. Mary had never understood why a guy would want to fuck a girl's ass when two inches away her vagina must have been ready, willing and able to accept what he had to offer.

Mary had been with only one boy. His name was Jack and it wasn't an experience she cared to remember let alone share. They had dated for a couple months doing the normal dating things such as going to movies, dances, playing miniature golf, bowling and some light petting.

One particular evening after they had been to a dance to celebrate her eighteenth birthday, Jack drove to a secluded area and after parking the car he slid the bench seat as far back as it would go and the two of them began their usual make out session. Up until now, she had enjoyed these sessions but tonight would be different. Jack soon had his hand under Mary's sweater and was fondling her breast through her bra. It felt good and although she wanted him to stop her curiosity got the better of her and she allowed him to unhook her bra and play with her breasts au natural. He soon had her sweater pulled up over her breasts and was sucking on first one nipple then the other. That sent shock waves through her making her pussy wet and her clit swell and tingle.

Before she knew what was happening he had his hand under her skirt and was pulling her panties to the side giving himself access to her little virgin pussy. He began sliding his middle finger up and down her moist gash which really felt good especially when he slid it across her sensitive, swollen clit. When he attempted to push his finger into her vagina she grabbed his hand and stopped him. He asked her what was wrong and she told him she was a virgin and didn't want to go that far. He said "OK then how about a hand job". Not wanting to be considered a tease, she reluctantly agreed. He opened his zipper and pulled out his cock. He took hold of Mary's hand, helped her place it around his cock and demonstrated how she should move it to get him off. Slowly Mary began to slide her hand up and down as he had instructed. In less than two minutes, he stiffened, his cock began to pulsate and he blew his load all over her hand. He grabbed a towel from the back seat and handed it to Mary to clean her hand then used it to clean himself. She asked if she had done it right and he said "you did just fine".

The following weekend, they were back at the same area and while fingering her slit, he suddenly, before she could stop him, shoved his middle finger into her to its hilt. She felt a sharp pain as it broke through her hymen. The pain only lasted for a minute before what he was doing began to feel good again. She had never expected to lose her cherry this way and was angry that he had done this to her after she had asked him not to the week before. The next thing she knew he was sliding her panties down her legs and pulled them off.

He unbuckled his belt, unbuttoned and unzipped his pants and pulled them and his briefs down to his knees. Then he pulled her butt across the seat so that she was lying on her back, crawled between her legs and began to rub the head of his cock up and down her wet gash. When he tried to push inside she stopped him again and asked if he had protection. He opened the glove box and pulled out a cylindrical package with three gold coin shaped objects inside. He opened it and took out one of the coin shaped objects, removed the gold foil wrapping and there was the first condom Mary had ever seen. He placed it on the end of his cock and rolled it down covering his entire penis with some left over. After moistening it with her juices he again began pressing himself against her opening. As she relaxed he slid inside. Three alternating insertions and extractions later he was fully planted inside her vagina. He pumped rapidly for only a couple of minutes before grunting like a pig, shooting his load and collapsing all his weight on top of her. He never brought Mary anywhere near an orgasm and apparently didn't care.

When his breathing returned to normal he gave her a quick kiss, pulled out, removed the condom, through it out the window, pulled up his pants and handed her panties to her. Still in shock over what had just happened, she put them on, re-hooked and adjusted her bra and straightened the rest of her cloths as he drove her home. When they got there, he reached across her, opened the door and gave her a peck on the cheek. He told her he had a great night and would call her. The sorry bastard didn't even walk her to her door. He never called and they never went out again.

What happened that night was nothing like what Mary had envisioned her first time would be. It certainly was not loving or tender and she decided to never allow a boy to touch her again.

Being very upset about her experience Mary needed to talk to someone about it. The only person she felt the least bit comfortable telling about that night was her lifelong friend and cousin, Bettie. Bettie listened patiently then lovingly held Mary in her arms and told her how sorry she was that her first time had been so horrible. She then confessed that her first time had been very similar but that her second boy friend had been entirely different making her realize that not all guys were ass holes. He had been so sweet, had taken his time, hadn't rushed her into anything and when she did decide she wanted to make love with him it had been a wonderful and loving encounter that she would always remember fondly.

Mary had a picture in her mind of how love making should be and after her talk with Bettie, she began to think that maybe she would give it another try some day but under her own terms and with the person of her choice.

There was a boy named Jimmy who she had swooned over since they first met in biology class their freshman year in high school. Jimmy was two months older than Mary and he was taller and bigger. He had been the number one pass receiver on their high school varsity football team and was in great shape. He stood six foot four inches tall and weighed about 195 pounds. He had thick wavy, coal black hair that never appeared to be out of place and dark olive skin. He was a straight "A" student whereas Mary struggled to maintain a "B" average. He was also extremely handsome but very shy around girls.

Some of Mary's girl friends had been told by their boyfriends on the football team that Jimmy's nick name was horse. Not because of his running ability which was legendary but because of the size of his manhood. It was rumored to be seven inches long when hanging softly between his legs as observed by his team mates in the shower room. From those rumors, Mary guessed that boys must check each other out as much as girls do. Jack, her only other so called boyfriend with whom she had lost her virginity only sported what she judged to be five inches when fully erect. It had been enough to satisfy him but had done nothing for her. It was also rumored that Jimmy's package had never been properly introduced to a pussy which because of his shyness she certainly believed.

Mary was very pretty and had a fantastic body which was in great shape as well. She stood five feet six inches tall and weighed 125 pounds with a 36 inch bust, 24 inch waist and 32 inch hips. She had shoulder length auburn hair that appeared more red than brown and usually kept up in a pony tail. She had dreamed of going out with Jimmy since their first meeting but no matter how much she flirted with him he never took the hint to ask her for a date.

Mary had one talent at which she excelled. That talent was music and especially the piano which because of her mother's insistence, she had practiced almost daily since the age of five.

Finally one Friday at lunch in the later part of their senior year she happened to mention her piano playing talent to Jimmy and he said he would love to be able to play but had never had the opportunity to learn. Mary suggested he come to her house and let her show him some basics. To her great surprise he agreed to come and give it a try.

She usually rode the school bus but today Jimmy was going to drive them in his slightly used but very well maintained red convertible. He very gentlemanly opened the door for her and she sat onto the buttery soft black leather seat and slid over to be next to where he would be sitting. He slid in next to her but unlike most guys never put his arm around her. Being a warm day, the top was down and the sun felt wonderful as they drove with the wind flowing around them.

When they entered her house she suggested some lemonade which he gladly accepted. Mary poured each of them a tall glass and as they drank they moved to the room with the piano.

Assuming the rumors to be true and Jimmy to be a virgin, she decided to go slowly to be sure he enjoyed his first time as much as she was sure she would and to be sure he would be back for more if things went well. She began by sliding up next to him on the piano bench so their thighs were touching and they could feel each other's skin. She was wearing a white pleated mini skirt and he had on a pair of shorts that hit mid thigh giving her a great view of his hairy, muscular legs. She let her knee gently graze his as she worked the petals while playing a slightly complicated number to demonstrate her talent. Afterwards she played a very simple piece then took his hand and placed it on the keys to show him how to finger them. She slid her finger tips softly over the back of his hand and then dropped her hand to his thigh and gently squeezed just enough for him to notice. Glancing down, she could plainly see a swelling down half the length of the right leg of his shorts.

He finished the piece and waited for more instructions. After having him practice that same number a few times she told him that was enough for his first lesson and asked if he would like some homemade peach pie. He said sure and they headed off to the kitchen. She cut a slice for each of them and poured glasses of milk. As they ate she stared into his beautiful light blue eyes, told him how handsome he was and boldly asked if he thought she was pretty. He blushed and said "Mary, you are the most beautiful girl I have ever known." He said he really loved being with her and thanked her for the piano lesson. She thought to herself, if I have my way you are going to enjoy the next lesson much more than this one.

She pushed him a little by asking which he enjoyed more, the lesson or being with her. He blushed even redder and said being with her was the best part and that he had dreamed of going out with her since they first met. She asked why he had never asked her for a date and he said he thought since she was so beautiful and popular that she wouldn't be interested in him and that he would be humiliated when she turned him down. She told him that he was so wrong and how she had wished forever that he would ask her out.

Jimmy overcame his shyness enough to ask Mary to go to a movie with him that night. Of course she said yes.

He picked her up at 6:00 PM and they enjoyed the movie and snacks at the local drive-in restaurant afterward. Not wanting to lose the momentum, he asked her to go out Saturday night for miniature golf. Again, she gladly accepted. They continued to see each other for several weeks until finally she invited him to her house for another piano lesson.

It was Friday afternoon and she knew her parents would not be home before six thirty or after. Now that she was going to have Jimmy all to herself for at least three hours she intended to find out for herself if the locker room rumors were true.

The new lesson went well and again her hand on his thigh produced the very noticeable bulge in the leg of his shorts. This time after the lesson as a reward for doing so well, she suggested ice cream which he gladly accepted. After finishing the snack she invited him to the den to watch some TV.

She snuggled up close to him on the sofa and again placed her hand on his thigh. Immediately the bulge returned to the leg of his shorts and knowing how shy he was she took the initiative and reached for his arm to place it around her shoulders. He was so shy he would barely touch her so she took his hand and pulled it to her breast. Her breasts weren't large. They were a nice firm "B" cup and perky. She really didn't need a bra to hold them up and was intentionally not wearing one today.

She folded his fingers around her breast and soon he got the idea that he was to gently squeeze and caress it. As he did, the swelling in the leg of his shorts extended until it was hitting her hand. She obliged it by lifting her hand and allowing the head and first three inches to slide underneath then lowered her hand onto it and began a gentle massage. He jumped a little and she demurely looked up at him and said "Oh! Did I hurt you?" Blushing again he looked into her beautiful pale green eyes and told her no, that she just surprised him. She asked him if what she was doing felt good and if he wanted her to stop. He said it felt great and he definitely didn't want her to stop.

She smiled up at him and asked if he liked the way her breast felt. He said "oh my yes", that it was very soft and firm and asked if what he was doing felt good. She assured him that he was doing just fine and asked if he had ever felt one before. Of course he said no. She then asked if he would like to see it and he blushed even brighter and shook his head yes.

She told him she would make him a deal and show him both of them if he would show her his cock. He stuttered an affirmative answer and she began unbuttoning her blouse. After the third button, reveling a limited view of her cleavage she asked when he was going to start taking off his shorts. He seemed to return to reality, apologized and reached for his belt buckle. By the time Mary had unbuttoned the last button of her blouse he had his shorts off but seemed very nervous about removing his boxers which sported a giant tent in front along with a large wet spot. To assist him she said "OK Jimmy, on the count of three, I will open my blouse and you pull down your boxers." He agreed and on the count of three her blouse disappeared leaving her naked from the waist up.

He pulled down on his boxers but the waist band caught on his raging hard cock. Mary tossed her blouse onto a nearby chair then reached for the waist band of his boxers and pulled it towards her releasing his monster to spring up and slap against his six pack abdomen. He pulled his boxers the rest of the way down and tossed them onto the chair to join Mary's blouse. His eyes were riveted to her chest and hers to the beautiful prize that popped out in front of him pointing directly up at her face. At least part of the rumors had been correct. It was at least 10 inches long and as big around as her wrist. The head was brownish purple and leaking pre cum with a large clear pearl drop at the tip followed by a stream running down the underside of his cock half way to his balls. There were large pulsating veins the size of a pencil running around its full length from the base to the back of the crown.

Mary stood mesmerized; staring at it with her mouth open for what seemed like a very long time but in reality could only have been a few seconds before returning to her senses. Jimmy's eyes never left her breasts. He appeared to be focused on the quarter size light pink areolas and the slightly darker nipples which were the size of two pencil erasers joined together. When she asked him what he thought of her breasts he said they were the most beautiful he had ever seen. She asked him how many he had seen and he confessed that hers were his first other than those in his dad's girly magazines.

She told him that of the three cocks she had seen his was the largest and most beautiful and asked if she could touch it. He said sure and when she did he quickly turned to the side as his cock began to jerk uncontrollably and shot five long strings of pearly white cum in an arch four feet across the room splashing onto the floor. Mary was amazed at the force with which his ejaculate traveled.

He began to apologize for making a mess and she told him that she had heard the first time a guy is touched by a girl he often has an orgasm and that it was nothing to be embarrassed about. She asked him to take off his shirt so she could feel his bare chest against her breasts. He did as she asked and she stood on her tip toes, put her arms around his neck and kissed him with all the passion she could muster. His thick chest hair tickled her nipples making them harden. He felt them poking into his chest and smiled to himself as he wrapped his strong arms around her and pulled her tightly to him crushing her soft, warm breasts against his chest. She told him to sit down while she went to get something to clean him and the floor.

While she was in the bathroom getting a towel and wash cloth she removed her sopping wet panties and skirt feeling that Jimmy would be more comfortable being naked if she were as well. She returned to find him obediently sitting on the sofa with his soft cock lying across his left thigh. She gently cleaned off his cock with the warm wet wash cloth then laid it between his legs. She gave him a show by allowing him to watch her cute little butt wiggle as she crossed the room and spread her beautiful legs while bending down to clean his cum off the floor. She could see in the mirror on the wall that he was focused on her naked pussy so she took a little more time than needed to get the job done. When she turned around his eyes zeroed in on her furry little auburn haired triangle whose apex pointed in the direction of his main interest.

After discarding the dirty cloth and towel, she returned to the sofa and plopped herself down onto Jimmy's lap facing him with her knees on either side of him. She pressed her breasts against his hairy chest, wrapped her arms around his neck and placed a firm wet kiss on his lips. They spent the next few minutes making out allowing their tongues to play together and their hands to caress each other's exposed skin. Mary pulled back to look in his beautiful light blue eyes and found him smiling but having the look of a deer caught in the head lights. She asked if he was all right and he said he had never been better. She could feel his beautiful cock swelling against her pussy lips and knew he could feel her juices leaking onto it.

His tongue began to lick his lips and his breathing became a bit rapid. She told him that he looked as if he would like to eat her. He said "you do look good enough to eat." She then asked if anyone had ever told him about oral sex. He said he had heard about it but didn't know how to do it or if girls actually liked it or thought it was gross. Mary crawled off his lap, pressed his knees apart, placed one of the throw pillows on the floor between his feet and knelt between his legs. She ever so slowly slid her hands up his thighs. Reaching his crotch, she began hefting and rolling his balls with one hand and took hold of his beautiful cock with the other. She held it upright as she flattened her tongue and licked him from balls to crown. He was profusely leaking pre-cum again and it tasted wonderfully sweet and salty. She kissed up one side and down the other while flicking her tongue back and forth. After licking all around its head, she fed it and two inches of the shaft into her mouth and began bobbing her head up and down while lapping at the sensitive underside below the tip with her tongue.