Chapter 01: The First Night
I dated many women in college but only two stand out. The first was Gina and if you follow my stories you will notice that her name comes up regularly. Gina was two years behind me and we met when she was a freshman. She was beautiful, raven-haired, voluptuous, and built for luxurious pleasure. Her smile was magical and she used it to devastating effect. She had lovely legs, a slightly generous ass and hips, nice heavy breasts, and a stunning face. She was the perfect princess who wanted to be treated like a whore in bed.
She didn't start that way. She started as the perfect princess who thought she would wait until marriage to have sex, and thought the very idea of oral sex was disgusting. She was a virgin when we met but she learned fast. Eventually she became addicted to sex and went far beyond my means to provide for her. It's sad really. She equated sex with intimacy and love, so anytime she was feeling emotionally needy or in any way frustrated or unsatisfied she channeled those needs into the need for sex. While it was exciting at first it was ultimately very unhealthy. The sex never fulfilled her need for intimacy and so the need increased, a spiraling cycle which eventually ended in ruin.
On the road to this destruction of our relationship we had some great times. At one point when we were well into our sexual relationship we reached a bit of a plateau. We had taught each other quite a bit by being very honest and sharing with our activities, but at a certain point it became a bit boring and we needed a change. Neither of us was experienced enough to know what we wanted to do, but I had a naughty streak a mile wide and I knew from experience that where I lead, she would follow.
I suggested that we have "in charge" nights where one or the other of us would be completely at the other's whim. I am a very polite guy and always afraid of pushing a woman farther than she wants to go, so I rarely pushed for anything truly unusual. Still, I had the desire and the suspicion that she would play along with quite a bit.
She agreed to the plan but was a bit confused about how it would work. Like I said, her imagination was not up to her willingness. I suggested that I go first to give her a taste of what it meant. I promised not to push too far, but made sure she realized that the event would be all about the "master's" desires and satisfaction and that nothing should be taken as an insult or a lack of consideration. This would be a subordinate thing, and what the person in charge says, goes. It wasn't a submission/domination thing so much as a luxury for the person in charge. At least that's how I thought of it.
She agreed that I would go first and we set a date, a Friday night when we knew we would have nothing else distracting us. It was to be at my dorm room and she would come over shortly after dinner.
As the date approached I was nervous. What would I ask for? How would I conduct myself? I didn't want to be aggressive and forceful because that just isn't appealing to me, but I didn't want to just settle for an extended backrub and blowjob either. I wanted to push our envelope a bit without scaring her. It occurred to me that we might want to have lists of things we absolutely would not do, but I didn't think that would be an issue for this coming Friday.
I eventually came up with some good ideas and arranged the required props for the evening. It wasn't much but I thought it would help to loosen us up a bit and get more comfortable communicating during the act.
Friday came quickly and I was ready. A quick shower after dinner and I was in my dorm room waiting for her to arrive. It was very difficult to keep from fidgeting terribly as I waited. I did some homework – poorly – to pass the time, knowing that Gina was commonly late.
When she knocked on the door I jumped a bit even though I expected it. I let her in quickly and locked the door behind her. I took her jacket and hung it in the closet, kissed her hello, and made sure she was still on the same page.
"Are you still OK with all this?"
"Absolutely. I've been wondering all week what you have planned. I'm ready to give you everything you want, baby."
"Good. Come in."
We came into the larger part of the room, all of 14 feet long and 8 feet wide with the "foyer" area just constricted by the large closet. In the main area was my loft high above the floor holding my bed near the 9-foot ceiling, a desk, dresser and chair provided by the university, and a huge pillow I had brought with me from home. I sat in the chair and motioned for Gina to stand near the pillow. I already had music going, mainly to cover our noises, and candles burning to set the mood.
"Take your clothes off."
She smiled and did as she was told. First came the sweater and bra, as she knew I loved a topless woman in denim. She touched her breasts a little and giggled, performing for me. Then she kicked off her sandals and stripped off her pants and panties. Standing naked in front of me, she waited.
"Stand close to me, right in front of the chair, and don't move unless I tell you to after that."
She complied, making those 3 steps as sexy and slinky as she could. And believe me, she could. As she stood directly in front of me, her full breasts at my eye level, I reached out and gently caressed her body. I started where her collarbones met at the base of her neck and moved my hand down, slowly, until my fingers brushed her fluffy brown pubic hair. She shivered at my touch and cooed a little. I moved my hand up under her left breast and cupped it, letting my index finger stimulate her swelling nipple. I pinched it very lightly with finger and thumb, knowing that she liked a bit stronger stimulation here than many women. Her eyes closed and her smile deepened.
"Lick that nipple. Make it sexy." I said, dropping my hand to her hips.
She had never done that before and looked a bit surprised, but she did it. She lifted her heavy breast with her left hand and bent her head down to get her tongue in range. She gave fabulous head so she knew what to do with her mouth, and her natural instincts kicked in here. She flickered her tongue on the nipple a little, then dug in hard around the areola. My hand moved back and forth across her hips and bush, not touching her clit but stimulating the area. She was now taking the whole nipple into her mouth and sucking it hard, pulling it back out to make a popping sound, then biting it a little with bared teeth.
Like I said, she was a natural at giving head and just as good at making this look good. It gave me some ideas for the future, but for tonight I still had my plan.
"Stop. Turn around." She turned and showed me her generous ass. Her skin was exquisite and tight at that tender age of 18. I continued to brush my hand around her back, hips and thighs, only occasionally brushing her sensitive parts. Gina was always hungry for foreplay so I thought I'd giver her a little tonight, though not nearly as much as she usually received. She was a glutton for foreplay and I expected my upcoming night of servitude to her to be full of long, slow massages and oral favors.
I loved her ass. I go through phases of being a leg man, an ass man, a breast man, etc, and that night I was all about the ass. Hers was just a little generous but it gave her a wonderful curvy form. Her waist was high and small and her big tits swelled invitingly to give her a classic hourglass figure, like a pinup girl from days past. I lifted both hands to cup her ass cheeks and gently massaged them, occasionally running my fingers up her back and around front to her breasts. Gina loved absolutely any kind of attention so I'm sure she enjoyed the slow, luxurious ass massage I gave her.
I reached over to the small pile of accessories I had collected and opened a bottle of lubricant. I put a fair amount in my and hand and then started to use it in her butt crack. She cooed a little and squirmed as the slippery stuff coated her private parts. I continued my massage, but now I was running my fingers over her little pink asshole as well as her pussy.
I kept this up for quite a while, giving her just enough stimulation to get excited but nowhere near enough to approach orgasm. I was just giving her a different kind of foreplay. I was also getting accustomed to the feeling of me playing with her back door. I knew from experience that no matter what she protested, once faced with the prospect of trying something new she would almost always plunge right in.
"Go lay down on the pillow, face down with your ass in the air and legs spread," I commanded as I removed my hand and grabbed the bottle for more lubricant. She did as she was told and settled onto the monstrous 4-foot square pillow. Her pale white ass beckoned to me as I approached her.
I quickly disrobed and then went down on my knees behind her. With a new coating of lubricant I returned to my probing, but now her cheeks were spread and I had unfettered access. I started to probe a finger into her tight back door and was rewarded with a little sigh and some squirming. She was not averse to my attentions and allowed me to get my index finger inserted to the first knuckle. I let it sit there a while as I massaged her clit with my other hand, still keeping everything calm and slow.
I could feel her sphincter spasm a few times on my finger, and when they subsided I started to push deeper. I was slow and cautious because I didn't want to hurt her, but she had another idea. She pushed back hard on my finger and embedded it all the way inside her. I was surprised and very aroused and had a full erection by now.
I slowly retreated my finger and then pushed it back in with ease due to the lubricant. I put my middle finger out and entered her vagina, then slowly pumped both fingers into her holes. She was enjoying this deeply now, pushing back against me and giving happy little moaning sounds. I hadn't expected it to go this well but by now I was wondering if I could get my dick in there. I figured that would be something for later in the evening if at all so I put it off. Besides, I really wanted a blowjob and figured I wouldn't get one after I had that thing up her ass.
