Dear Diary 05

A few entries later, I found probably the greatest oops of my sexual life so far. It read: NXRI – Christmas 1987

Paul – Christmas 1987

I have been dating Paul for a few months now, and things seemed to have been going pretty well between us. A country boy from Oregon, I found Paul to be a lost and lonely boy more than an attractive man when I first met him. 

His sense of humor, ability to listen and be attentive won me over eventually and we started spending more time together. We became friends first, lovers later. He was dating someone else when we met in one of our mutual classes, where we always sat next to each other, at first discussing the lessons, later on going out to lunch or to a movie and eventually, when he broke up with his girlfriend, one thing led to another and, well, after a party one evening, we ended up in bed. 

Paul turned out to be a gentle lover, just as attentive in bed as he was in conversation. He liked kinky stuff like light bondage and blindfold. I trusted him immensely and never felt threatened. 

I liked making love to Paul, especially when it turned into a hard fucking, and he lost himself in a moment completely, oblivious to anything around him, even myself. He would pound away furiously, unable to stop, probably even if the building was coming down. 

Paul always seemed to be fascinated by anal sex, although he had never done it, and I had no experience in it, either. I began noticing that a great majority of the porn movies he was bringing to my place were turning out to involve anal sex, some movies were on that particular subject exclusively. We talked about it and decided that we would try it some day. 

That some day actually turned out to be the evening of our talk. Of course, I sort of expected that to happen, but still, I was caught by surprise to a point and a bit worried. I kept thinking of Paul and the time just before he is ready to cum. I couldn’t see him go berserk on my ass like that and not hurt me. 

Paul promised solemnly that he would be careful and would not do anything that would be uncomfortable to me. He even offered that I could take the vibrator we were sometimes using to spice up sex and try it on him. 

We started off slowly, kissing and petting, Paul giving me oral sex and making me cum. It all started off very nice. After I had clamed down, he turned me over and started kissing my back, scratching it lightly with his nails, working his way down to my ass, spreading the cheeks and licking my little hole. 

The feeling was odd, not very pleasurable, but the idea of what we were about to do was certainly very appealing and I found myself enjoying the action more than I expected I would. 

Using KY jelly, he squirted some inside my ass and lubed his finger, gently and carefully inserting it inside of me. Again, the feeling was odd, beyond anything I had ever experienced, but it didn’t hurt so I didn’t stop him. 

I noticed that Paul’s dick stood in a hard salute to me since the moment I agreed to try anal sex and I didn’t have to do anything else to keep him that way. He was too eager to get to the action to be able to let himself be teased any longer. 

As we got to the intercourse part, however, Paul pushing his dick inside my virgin ass with less patience than he had ever displayed before, I started hurting more than I expected and after a few moans and cautions to please go slow, he finally buried his entire dick inside his desired destination. 

Now that it was finally in, I couldn’t bear to think of it moving in and out, I most certainly didn’t want him losing his mind and fucking me hard like he normally did and to Paul’s great disappointment, I pulled away and we stopped. 

He was kissing me later and reassuring me that it’s okay, but the disappointment on his face was evident. We tried to have sex in a normal way, but he couldn’t perform. I felt awful. I offered we should try again, but he declined of which I was grateful for. Even though I had his dick in my ass for less than a minute, I could still feel the discomfort which it had caused me. 

We fell asleep that night, unsatisfied and both disappointed. Paul avoided spending the night in my place for a few days afterwards. 

Christmas was just around the corner and Paul had left Chicago for home to spend a few days with his family, returning on Christmas Eve, determined to spend it with me, feeling sorry over my decision not to go to Oregon with him and absolutely refusing to go home to my family. I’ve been away from home for three years now and I am not ready to go back, yet. As annoying as the topic of Christmas was to me, I loved him for being so sweet and attentive. 

“santa Clause!” I heard him yell even before he opened the door and I was genuinely happy that he had returned in time to spend Christmas with me. I was down more than I had expected to be. The celebratory atmosphere of the festive season had gotten to me and I hated to see numerous shoppers running back and forth, carrying huge bags filled with presents, Christmas trees on every corner, Christmas music in every store, restaurant and even elevators. I was ready to scream!

He entered and we fell into an embrace, kissing passionately as if he had been gone for months, not less than a week. I noticed a small bag with images of little Santas dancing around a Christmas tree, accompanied by the necessary gift bag filling paper, undoubtedly containing my present. 

“Later,” said Paul. “First, we’re going out to dinner.” 

We splurged that evening, aware that restaurants were closing early that evening. We ate in Greek town and then walked some thirty blocks to my place, enjoying the unseasonably mild night, making the romantic evening perfect. We stopped at our friend’s dorm room, had a few drinks with people we knew from classes and finally headed to my little apartment, determined to spend the night in lovemaking, warming ourselves up by occasional stops to kiss and slip our hands inside each other’s coats, touching, rubbing, squeezing and giggling like kids. Life was good and I was happy. 

When we entered the apartment, Paul took off my coat and with great ceremony presented me with the bag, which he had brought with him and I had to admit that I was absolutely dying with curiosity. Given that we were both students, poor as church mice, any kind of present was deeply appreciated. 

Paul dragged me to bed where we sat down and I was finally allowed to look into the gift bag. I pulled out two presents. 

“The green one first, Nik.” Said Paul and smiled mischievously. “The red one later. That’s actually for both of us, maybe even more for me than you, but that one later, okay?”

I tore the green wrapping of a small box, my heart racing as I realized that it must have been containing jewelry, definitely way beyond Paul’s modest means. I was grateful already. I slowly opened the box and a beautiful golden pendant of a ram standing on its hind legs and kicking the front ones up high made me gasp. 

“Oh, Paul!” I yelped, with great embarrassment realizing that I was just about to cry. 

“I realize that this would be more appropriate for a birthday present, but I saw it and liked it, and thought you’d like it, too.”

The symbol of my star sign was absolutely gorgeous. I felt a pang of shame over my modest gift for Paul, a sweater I had knitted myself, which was still tucked somewhere in my closet, unwrapped. 

“You like it?” he asked worriedly.

“Are you kidding? I love it!” I said and hugged him. Life indeed seemed to be good. 

“Now the second one!” he said, fidgeting on the bed like a little kid. 

I looked at the small package wrapped in the red paper, bigger than the first one. I tore the paper off with trembling hands, still completely impressed over the pendant and almost screamed in surprise.

“What is this?” I asked, knowing exactly what it was. 

“It’s desensitizing cream, Nik. “ I closed my eyes. When Paul put his mind to something, there was nothing to persuade him otherwise. “We can try again, you know. It won’t hurt, Nik. Please?”

I gave in. How could I not? Paul make sure I was happy this particular Christmas, the least I could do is make him happy, too. 

We undressed slowly. Paul taking my clothes off and kissing every newly unclothed part of my body. I did the same for him. He made me cum with his tongue and fingers. I made him hard with mines. We fucked for a while with Paul very carefully not going too far as he didn’t want to cum too soon and fall asleep. This was the moment in which he wanted to do it. If the moment was lost, it might never happen, or if it did, it wouldn’t feel as right as at this particular time. 

Paul unscrewed the tube and used a generous amount of the cream to lube me up. I believe he put in three or four times more than required. He didn’t want to hurt me and at the same time was so eager to do what he fantasized about for so long, common sense went out the window for both of us. 

“How does it feel?” he asked and I giggled. 

“How do you think half of that tube feels in my ass?” Paul didn’t laugh. He was too concentrated on what he was doing. 

He pushed his finger inside my ass, and I didn’t even feel it. He pushed a second one in, again I felt nothing. We tried it with a vibrator and this proved to be just as easy as the fingers, so with great hopes, Paul finally positioned himself behind me, kneeling on the bed and pushed his dick inside my ass. 

I felt that, but still only just. It didn’t hurt at all, it wasn’t uncomfortable, and he wrapped his arm around my hips, with his fingers now carefully cleaned with a washcloth softly rubbing against my clitty. 

He made me cum like that. Hearing his moans and groans, his heavy breathing and feeling his expert fingers on my bud was a blissful pleasure. He made me cum again and then again. 

Some thirty minutes later, my legs stiff with the pressure of Paul’s heavy pounding against me, my stomach began cramping from the invasion deep inside my gut. He was very careful to clean his fingers but we had both completely forgotten that without use of a condom, he had desensitized himself as well as me and it had taken him close to an hour of labor to make himself cum. He enjoyed it throughout, he said later. We were both covered in sweat despite the chill in the room, and the bed was in a complete disarray. 

Pillows and comforter had fallen off a long time ago. The sheet was pulled off the corners and was now half hanging off the bed, the two of us fucking like two rabbits on the naked mattress. 

After a while, when I couldn’t stand him touch my clitty anymore, certain that he had left bruises all over my hips and shoulders, having clung to them desperately, he had finally let out that last groan of pleasure, which told me that he had cum. I couldn’t feel his dick throbbing or squirting. 

“Fuck, Nikkie! That was good!” he said and all I could do was moan agreement. I vaguely remember him pulling the comforter off the floor and throwing it over us, and then we were both asleep. 

As I am writing this, it’s the evening after our little escapade. I can barely walk. I spend half of the day in bed, the other half in the bathroom, sitting on the toilette, crying with pain that I felt from the previous night. 

How could I have been so stupid? Why would I let him do that to me? To top it off, without a condom. I’m not sure that the use of a rubber would prevent his feeling to evaporate, but now I think anything would have been better than what had happened. 

Never again! 

------

I laughed out loud as I finished reading. Never again, indeed! Of course I still have anal sex, but I have to admit that it had taken me years before I let myself do it again. Certainly not with Paul. 

Poor Paul! He felt so guilty; I thought he would never make love to me again. Eventually, we slept together, but it never seemed to be as good as it used to be. We never tried anal sex again. A few months later, with exams taking all our time we gradually grew apart and one day he came to my place, looking sad and ashamed, admitting to dating someone else for a few months. 

We broke up and I wasn’t surprised when I saw him at a party a few days later with his new love. A guy. That’s where his strong fascination with anal sex came from. I just hope his experience was better than mine.