I met Olivia in medical school. We were both young, enthusiastic, and ready to conquer the world. For the first 2 years, we were in the same group of 10, following our mentor wherever he went. We listened to his talks and examined the same patients. In the 3rd year, after writing a manuscript together, Olivia and I clicked and started dating.
Even though both of us were already in our 20s, before that time we were too busy studying and thinking about our careers to engage in serious relationships. As a result, our initial experiences in intimacy were not very successful. We both knew the theory, but neither had a complete sexual encounter before.
Our first try at an intimate kiss ended up with her biting my tongue. In our second attempt, the kiss was hardly pleasant, but at least without hurting one another. We liked each other too much to give up, and one evening, we tried again. We French kissed, and my palm cupped her covered breast. I got so excited that I came in my pants within seconds. She realized what had happened and reassured me it was OK, but I used the first opportunity to run home.
Over the next month, we overcame most hurdles, and 2 months after our first date, we managed to successfully complete sexual intercourse, with both of us reaching a reasonable climax. We celebrated it in a bar and got drunk. We returned to our apartment and had another session. At that time, the act was much more pleasurable. We kissed each other, pledged to love each other for eternity, and slept for 24 hours, missing our class...
...
In the following weeks, we couldn't keep our hands from each other. Every opportunity we had, we dedicated ourselves to sexual fun. Not all encounters remained in my memory. However, some firsts were engraved there forever.
The first time I saw Olivia's breasts. Caressing them above her clothes was initially exciting since I felt the softness and knew others were not allowed to do it. However, she was very shy and wore padded bras. When she first removed her bra, and I noticed the gorgeous D-cup mammaries with dark pink nipples, I was stunned. Since that day, they have become my favorite toys.
My first time licking her cunt was another memorable event. Initially, she refused to let my face near her vulva, scared that I'd hate the shape or smell. Once, we were tipsy, and she was partly out of it. I took a good look, sniffed her juices, and even licked her into an earth-shattering orgasm.
Olivia's loss of her virginity was more traumatic than we thought. I read beforehand that most hymens were membranes with holes in them. So, when we were ready for it, somewhat drunk and highly charged, I shoved my penis into her pussy, hoping for minimal pain, which would disappear once the constant friction aroused her again. Unfortunately, she bled profusely, burst into an uncontrollable cry, and vowed it was our last intercourse. Her resistance lasted one week before our horniness took over, and that time the experience turned out much better.
Our first doggy style was not meant to be. Our plan was a routine missionary, but Olivia had a nagging muscle pain in her calf that improved when it was flexed. I jokingly offered a doggy position. She was highly aroused and agreed, warning me she'd kill me if I inserted my tool in the wrong hole. This position was a wonderful success and remained one of our favorites.
Porno movies taught us that titfucking was supposed to be especially pleasurable when done with a partner with large tits. Olivia's were definitely in the category of above average. Our try was, how shall I say it, MUCH BELOW PAR! The lack of experience may have played a role, but her creamy boobs did not generate enough friction, and I became frustrated, eventually cumming vaginally.
For my 29th birthday, Olivia made me a chocolate cake, and we drank a lot. She chuckled, "Honey, next year, you may be too old to enjoy, so this is your only chance to have me any way you choose." Without thinking twice, I blurted, "I want you anally." I fantasized about her cute bubble butt several times before, but never dared mention it to her. She attempted to change my mind, offering me to use her other 2 holes as many times as I wanted for the next 24 hours. I declined, and then left her to watch a soccer game on TV. She came crawling an hour later, saying she'd do it on certain conditions: I was to use an abundant amount of KY jelly, do it very slowly, and if her pain was too much, no more tries. I agreed. I read 2 articles and even saw an instructional video on anal sex for beginners. I started by ensuring she drank 2 glasses of her favorite white wine and became very horny: I kissed the side of her neck, kneaded her titties, and licked her clitoris. I placed her on all 4 with her legs apart, moved behind her, and continued tweaking her nipples as my erect pecker tickled her vaginal entrance. Then I slowly inserted my pole into her pussy, and at the same time, my fingers began smearing jelly onto her crack, poking lightly on and around her puckered hole. She tried to relax her sphincter, and my forefinger slid inside easily. Instinctively, the sphincter contracted on it, but gradually it relaxed again. I moved my finger circularly, enlarging the opening, eventually slipping a second finger in. With my prick drilling her cunt and my left hand massaging her breast, she tolerated it quite well and even countered my movements. Then I removed my fingers and slowly inserted a medium-sized anal dildo. She liked it and moaned loudly. I moved it in and out, now and then changing directions - Slightly right and then left inside her. After a long moment, I removed the artificial tool and began penetrating with my member at a snail's pace. When she first felt it invading her backside, she gasped, but it went in without a hitch and no major pain. Within seconds of fucking her tight anus, she was begging me to do it faster. I intensified my strokes and used my fingers to rub her G spot and excite her clitty. We climaxed almost simultaneously. Once we were done, she ran to the bathroom. When she was back, she kissed me, "Darling, you were amazing. You were patient, and my orgasm was one of the best ever. If you are in the mood for a similar thing in the future, just give me a sign... I really liked it."
Later, we enjoyed sex so much more: Doing it on the floor, on the kitchen table, on the washing machine, and even in a public park. The sky seemed to be our limit.
In our fourth year, we started talking about our fantasies. We agreed that each would fulfill the other one's wish on his/her birthday.
...
Olivia's was first. She blushed and blurted she wanted to be dominated, manhandled, tied, and even punished, assuming there was no severe pain involved.
Her birthday happened to fall on a Friday. I arrived home earlier. When she returned from class and opened the front door, there was a note: 'Put on the blindfold you see on the table, and undress. I want you in your birthday suit. Once you are done, announce loudly your readiness. Mistakes won't be tolerated, and a harsh punishment will follow. Your Master.'
From behind the door I was hiding, I could hear her giggle. A couple of minutes had passed and I heard her voice, "Sir, I am ready for you." I approached, checked that the blindfold was placed right, and she could see nothing. I didn't say a word. Next, I grabbed her hand, led her to our room, tied both hands behind her back, and stood her near the bed's edge facing in my direction.
Subsequently, I removed my shoes, went to the living room, and walked around. I began whispering loudly, knowing she could hear my voice but not what I was saying. She called me, "Noah, the deal was YOU would be the boss. No other participants allowed."
