Nan

My grandmother was such a remarkable person and after reading the stories in her notebooks, my respect for her has only increased. I still don't understand how such a confident, free and liberated spirit could produce a child so diametrically opposite in every aspect as my mother is to her. Maybe traits skip a generation but my money is on my controlling manipulative arsehole of a stepdad has a lot to answer for.

This story occurred a few months after her losing her virginity to a stranger in unusual circumstances. It is not in chronological order but it is important in explaining Nan's Journey of sexual discovery and the twists and turns along the way.

XXX

I had long ago lost interest in the flickering light coming from movie on the big screen behind me. We were parked in the drive-in as far away from the nearest car as possible. The roof of the Oldsmobile was locked down tight on that cool night. The cold air wasn't the reason the roof was down but it did help to cause the windows to fog up which conveniently obscured what was taking place inside to any casual observer glancing our way.

I was astride Dan's lap on the front seat of his car. My dress fanned out on the seat covering the fact that Dan had his pants pulled down and I was riding his hard cock. I lifted myself up on my knees and plunged my body back down to impale myself again, and again. I was enjoying the sensation of being penetrated in a slow rhythmic motion and was in no rush to stop. Dan would be a long time coming this time. I had already sucked him off earlier and it was now time for him to pleasure me the way I wanted. I loved the sensation of that cock plundering my pussy as we ground our pelvis together at the end of each thrust.

Dan was the latest in a growing list of fit young men to sample the pleasures of my body. I lost my virginity to a stranger in unusual circumstances and then ended up being spit roasted by two frat boys in their fraternity basement almost immediately after. It shouldn't have happened as I was not brought up to be that sort of girl. I don't have any regrets about losing my virginity. It opened my eyes to a world of pleasure that I hadn't even known existed. In retrospect I should have been more circumspect with the boys. I was on a sexual high and just wanted to experience more.

Word spread like wildfire across campus that I was a girl that put out. As a consequence, I was inundated by offers to take me on dates. Nearly all of those dates were a one-time thing that ended abruptly if I didn't put out or more disappointingly for me, ended just as abruptly if I did put out. They all exploded so fast that I didn't even get the chance to become aroused before they would shoot their load leaving me thoroughly dissatisfied. At least two of the guys I knew were virgins so they had some excuse but I suspect some others were also virgins given their lack of staying power.

Dan and I had sex once before but never considered him as my boyfriend, He was just a guy that I wanted to have sex with. He wanted sex, I wanted sex and we had a mutual understanding that saved us the hassles of fumbling around with someone inexperienced. He was significantly better than most of my other partners. It didn't seem right that while I had acquired a reputation for being the campus slut, he had acquired a reputation of being the campus stud. I was treated with shock and distain while he was lauded for doing exactly the same thing. I didn't care what other people thought of me and I would live my life the way I wanted, as if nothing was wrong. If anyone was going to make an issue about my behaviour then I would cut their small mindedness out of my life and be the better for having done so.

Fortunately, my two roommates Barbara and Elizabeth were not like that. They were definitely shocked when I first described to them how I lost my virginity. Their insulated and conservative upbringing had not really prepared them for the realities of the world. I had been just like them until it happened to me. The scandalous shock on their faces when I told the story couldn't completely conceal the heightened sense of arousal washing across their faces.

When I retold the story and it was the same for every one of my subsequent sexual adventures. They would wait in our shared room and ambush me as soon as I got home from a date. They wanted to know every tiny intimate detail no matter how small and insignificant. To be honest I think they got a great deal more pleasure from living vicariously through my sexual exploits than I did. Both were clearly interested in sex but were too timid to try it for themselves. Often times my re-telling of a sexual encounter took much longer than the actual deed did. Their constant need for ever more detail made me guilty of the occasional embellishment. At least I understood what the muffled sounds emanating from the girls' beds late in the night were all about. When I first moved in, those noises had me confused because they would stop as soon as I made any sound.

At least I wouldn't need to re-tell my story tonight. Babs was away for the whole weekend visiting her boyfriend's home for some family event. Beth was in the backseat of the same car and the main cause of my arousal. Beth lay at a slightly awkward angle across the back seat with her dress bunched up around her waist and her panties hanging loosely on one leg. Tom, the guy she was with, was kneeling in the seat-well and had his pants pulled open and was trying to position the tip of his cock in the wet hot centre of her spread legs. I was about to watch my friend lose her virginity and the vision was such a turn on.

I never thought that Beth would go anywhere close to doing what she was about to do, given how timid and conservative she had been with Tom at the start of the evening. Dan and I had organised to meet up and see a movie at the drive-in before I knew that Babs was going to be away. I felt bad about leaving Beth all alone so asked if she would like to come with us. Dan was ok with that, and said he had a friend who could come to keep Beth company. It didn't occur to me at the time that Dan's friend would expect Beth to be agreeable to sex.

Dan and Tom picked us up at our dorm and drove to the outskirts of town where the drive-in was located. Both the boys had been drinking and had a bottle of hard liquor they were sharing. Dan handed me the bottle and I took a large swig. We were all underage but the fraternity boys never seemed to have any trouble getting their hands on any alcohol they wanted. It was another wicked adult pleasure that I now enjoyed that would have horrified my conservative family back home.

I passed the bottle back to Beth in the back of the car and she took a small sip. The action caused her to cough and splutter and almost sprayed the lot over the interior before finally managing to swallow it in a coughing fit. It was clear from her reaction that Beth had never tasted alcohol before and she was trying to keep up with me and not make a poor impression. The boys laughed at her but eventually relented and gave her a cup and a bottle of coke to mix the drink after which there was no repeated coughing fits.

After arriving at our secluded spot at the drive-in, Dan hooked up the speaker. He then slid himself across the bench seat to my side. We started making out just after the advertisements finished and the movie started playing. Tom and Beth on the back seat were on opposite sides of the car watching the movie and continuing to pass the drink back and forwards between them. About fifteen minutes into the movie, Dan pulled open the top of my dress, exposing my creamy white breasts for all to see before beginning to maul them with his hands and mouth. My exposed breasts and hard little nipples definitely grabbed Tom and Beth's attention. They pretended to watch the movie every time I caught them looking at what Dan was doing to me. My actions provided the catalyst for Tom to make a move on Beth. He slid over to the opposite side of the car and pulled Beth into a passionate kiss. When they eventually broke to come up for air, Beth locked eyes with me. She had a frightened apprehensive look so I just smiled and nodded at her to give her encouragement. My actions seem to work and her body language relaxed. She took another swig but this time it was straight from the bottle. Tom launched himself into another kiss and Beth seemed to relax into his arms.

Happy that things were starting to progress well for my friend, I concentrated all my efforts on the hard hot cock I held in my hand. When I finally managed to release Dan's cock from his pants, I immediately started to stroke it from root to tip with a gentle caress of my fingertips. I knew Dan was getting close to exploding, by the way his body tensed up when I wrapped my fingers around the shaft just below the mushroom head. His cock was the thickest I had ever seen and my fingers were only just able to touch if I gave his cock a firm squeeze. In doing so I managed to bring him closer to his release. Not wanting a mess to clean up I slid my face down and placed my mouth over the bulbus head and bobbed my face up and down over his shaft. I had to really stretch my mouth open to stop my teeth from scrapping along his sensitive skin. There was no way I could keep this action up for long without getting a sore jaw but I didn't have to worry as Dan spasmed and started to flood my mouth with his hot sticky cum. I didn't mind the slightly salty taste and swallowed it straight down without spilling a drop. As I sucked the last trickle from the small hole at the tip of his cock, I climbed back up next to him. I then gave him a taste of his own cum with my wet sloppy kisses.

I was proud of how good I had got at giving blowjobs. The skill had served me well when I didn't want to go all the way with a guy or he refused to wear a condom. Tonight, the blowjob was just an aperitif in the lead up to the main meal.

My head was now above seat level, I could see into the back and observe how things were progressing between Tom and Beth. Since I last spied them, the couple had moved on, Tom's hand disappeared up underneath Beth's dress with the other firmly attached to one of her small breasts. They were still locked in an impassioned kiss and Beth seemed comfortable which allowed me to continue to concentrate on my own desire. I sat back on the seat next to Dan and lifted myself up enough to slip my panties all the way off from beneath my dress and I shoved them in my bag at the same time as retrieving one of the condoms I had stashed there.

Dan and I were content to snuggle up together and watch the movie for a while. I held his limp dick in my hand gently playing with it with light strokes of my fingers. Dan reciprocated and ran his hand up under my dress till his fingers found what they were searching for. I spread my legs wide to allow him full access to my opening. I was loving the feeling he was generating as his fingers ran up and down. After about ten minutes of this soft gentle massage my growing arousal was clearly evident and it was having a positive effect on Dan's cock which was well on its way back to full size and stiffness. Happy with my handywork I grabbed the condom and proceeded to roll it down his shaft. I flipped over into a kneeling position with a leg either side of Dan's lap facing the back of the car. I grabbed his cock by the shaft and positioned the tip at my entrance and with one slow luxurious motion lowered myself down imprisoning it in my snug little lubricated hole. I couldn't help but to let out a low satisfied moan which caught Beth's attention. Our eyes made contact and I gave her a smug satisfied smile as I slowly started to ride Dan's cock. It seemed to reassure her and give her enough confidence to continue what she was doing.

Beth had not been idle in the back seat, judging from the level of undress. Her dress top was open exposing her breasts, the skirt was bunched above her waist and her panties were half off. Tom had his pants open and his cock out and was in the process of trying to find her slit below her soft fuzz covered mound. Our eyes never broke contact as Tom continued to struggle to place his cock at her opening. When it finally happened, Beth flinched and got that frightened deer in the spotlight look again. Undeterred by Beth's reaction, Tom made another attempt to get his cock inside her. The attempt resulted in another failure except this time she let out a small cry of pain.

I was getting pretty excited riding Dan's cock but more exciting for me was looking at my friend about to have sex for the first time. I knew I wasn't going to last. My thrusting and grinding were increasing in tempo and intensity. Judging from the noises Dan was making, he wasn't complaining about what I was doing to him. Meanwhile in the back seat, Tom was making another attempt to claim Beth's virginity. I could see that the way their bodies were positioned in the cramped space the angles were all wrong. This time Beth really cried out in pain as Tom tried to force his way in. It was just at that point my orgasm hit and I selfishly closed my eyes while I rode it to completion.

It was the sound of Beth crying out once more that brought me back down to reality. Beth was in a lot of pain with tears streaking down her face as Tom's inexperience was continuing to hurt her as he tried to force his way in. I snapped into action immediately and started to smack Tom over the back of his head to make him stop.

"Stop it! Can't you see you are really hurting her?"

My violent and unexpected attack on Tom from behind brought the proceedings to quick halt. Beth was able to extract herself from underneath Tom and started to pull her clothes back into position while she continued to blubber and sob uncontrollably in the corner as far away from Tom as she could get.

Dan's cock had fallen out of me and I didn't care if he had got off or not. I was more concerned about my friend and making sure Beth was ok. I got out of the car and forced Tom out of the back seat while I hopped in with Beth to hold her protectively in my arms while she cried on my shoulder.

"Take us home now!"

It was an order that Dan followed without question and unhooked the speaker and started the car. As we left the drive-in, I could see the filthy look he gave Tom for spoiling an otherwise thoroughly enjoyable evening. We drove back to the dorm building in total silence except for the quite weeping coming from Beth. By the time we arrived, Beth's sobs had subsided to an occasional whimper. We got out without a goodbye and went straight up to our room.

Once inside the safety of our shared room, Beth broke down again. Her uncontrolled blubbering tears streaked her face so I led her over to my bed and held her comfortingly in my arms as we sat together. It took a while for her crying to subside enough for her to speak coherently for me to understand what she was saying.

"I thought I could be like you. I wanted to try it and see for myself after I saw how much you enjoyed doing it with Dan. I guess I'm not like you and when he started it hurt so much, I knew I couldn't do it. I wanted him to stop but he kept on trying and it hurt even more."

"It's ok, it's not your fault. He should have stopped when he could see he was hurting you. Sex is meant to be fun and pleasurable for both people."

"You don't think I'm a freak?"

"No, you have just had a bad experience that's all. Next time it will be better and if it hurts tell him to stop."

"It hurt so bad. You don't think he damaged me, do you?"

"No, but if you like I could check."

Beth slipped out of her dress and lay down on the bed before removing her panties. I climbed up between her spread legs and had a clear view of her opening. It looked slightly red and inflamed and there was a bruise starting to develop on the inside of her thigh but otherwise I couldn't see any other damage.

"Did he break me?"

"I can't tell from this angle. Open yourself up and I will have a closer look."

Beth spread the lips of her labia wide using both hands while I peered in close for a better look. My face was so close her feminine sent was overpowering.

"I still can't tell I'm going to touch you now."

I ran my finger through her slit and started to insert it into her body. Beth's body bucked in response to my touch. Instead of flinching away like she had done with Tom, this time it was like she was trying to increase the contact with my fingers. My fingertip hit her barrier and after some gentle probing it appeared to be intact. I could have stopped my examination right then, as I knew she was still a virgin but I let my hand remain a little longer gently caressing the insides of her folds. The shudder running through her body told me that Beth was in no hurry for me to remove my hand either. I knew Beth liked to masturbate late at night when she thought no one was awake. She wasn't as silent as she thought she was. Knowing how much better it felt when someone else touched you sexually I continued to play inside her folds and located her pleasure button and put pressure on the little stiff nub in a way similar to what I liked being done to me.

Beth's body bucked violently on the bed in response to my ministrations. She let out a growl of pleasure. I had so much wanted Beth to have a great first sexual experience but it was not to be. At least I could give her a climax as some form of compensation. Beth's body shuddered and shook and nearly folded in half. There was no mistaking what was happening to her and as she flopped back down on the bed, I did something really wicked. I latched my mouth over her lower lips and started licking. Her reaction was instantaneous and she grabbed my head hard and held me so tightly between her legs that I couldn't have removed myself even if I wanted too. Beth's next orgasm was massive and I learnt that she was very vocal. I'm certain that all our neighbours knew exactly what was happening in our room. When Beth finally relaxed and released me from her death grip I got up and slipped my dress off and climbed into the bed next to her. We removed the remainder of our clothes and held each other tight. With our naked bodies pressed up against each other sharing our body heat, it wasn't long before we both drifted off to a blissful sleep.