Hillary: the Summer of '92

From Benjamin Dornier's Journal

Tuesday, August 4, 1992

It feels funny writing this because it has been quite a while since I've found time to do any journaling. There have been almost daily meetings at school related to my new job and I continue to spend my weekends at the seashore with my family. Despite fears that my wife would somehow discern my relationship with Hillary, my lovely young student and lover, that hasn't happened. And my relationship with Hillary doesn't seem to have impacted my doing my "husbandly" duties, either. In fact, several times my wife's commented that this summer's separation seems to have done wonders for our love life. I'm not sure how I'm doing it, but apparently I'm managing. At least for now. And in seventeen days - but who's counting - my relationship with Hillary won't be a problem any more because she'll be heading off to college.

Hillary and I continue to see each other daily. After her parents came home, she had to stop spending the night, something both of us hated to give up. But their return didn't stop her from staying at my house until the wee hours of the morning. It did help that I gave her a glowing mid-course report on her performance in the summer school class that brought us together. The positive report wasn't a gift, either, she truly earned it. In fact, she'd almost taken over as discussion leader and had actually spent some time after class helping a couple of her classmates with their work, something she'd have never even dreamed of doing when she started the class. I am very impressed by the changes I've seen in her as a person and I've told her so numerous times, much to her embarrassment.

She got her period the last week in July, which bugged her, maybe more than it bugged me. "I hate this," she fumed after she told me what was happening. "We...we don't have that much time until August 21st and I have to go and get my damn period."

"Well, if I understand these things," I pointed out, "If you're regular, this means you won't be getting it again until the last week in August, right?"

"Yeah, so?" she retorted.

"Then you won't be getting it the last week we have, will you?"

That observation got me a fierce hug.

It was interesting that we still managed to have a great time together the week of her period, even though we couldn't make love. We talked about a lot of things, watched TV, made dinner, and generally acted like a comfortable married couple. I found it both enjoyable and troubling because I was worried that she might feel there was more of a chance for something more serious to develop between us. And I have to admit I was feeling far too comfortable with our relationship, too. It was really odd. On Fridays, when I was headed for the coast to be with my family, I found myself looking forward to the weekends as much as I ever had, if not more. And on Sunday night, when I was headed back home, I looked forward to seeing Hillary just as much. Maybe she wasn't the only one in danger of getting too attached.

Anyhow, Hillary surprised me again this evening. We were in bed. She was lying on her belly next to me while I trailed my fingers up and down over her lovely body, something I knew she loved. She was murmuring softly with delight while I did it. The sounds she was making were sounds I'd come to love hearing. And the skin I was touching was skin I'd come to love touching.

"Ben..." she said softly. She was lying with her head turned away from me and didn't look at me when she spoke.

"Yes?"

"There...there's something I want to ask you about," she said, sounding a bit tentative.

"You can ask me anything," I replied, continuing my caresses. "You know that."

"Ah...well...um...yeah, I know, but this...I'm afraid you'll think..."

"You're afraid I'll think what?" I asked. "Don't be afraid. If you have a question, go ahead and ask."

"Well..." She paused again. "Did you ever...with your wife...did you and she ever, um, ah, do it in the...um...rear?"

I have to admit that her question caused my partially hard penis to become a lot harder almost instantly. "You want to know if my wife and I have ever had anal sex, is that it?" I asked.

"Um...ah...yeah," she replied.

"No, we haven't," I said.

"Is that because you think it's...anal sex...you think it's perverted to do that?" she asked, her voice almost a whisper.

"Not at all," I said quickly. "I don't think anal sex is perverted at all. I have to admit we tried to do it, but it just didn't work for us, so we stopped trying."

"Oh," she said. "You really mean that, you don't think it's sick or perverted or anything?"

"Not at all," I told her. "Thousands, maybe hundreds of thousands, of people who engage in anal sex."

"Really?" she said. She turned her head and looked at me for the first time since our conversation started.

"Really," I said. "I think more people talk about it than do it, but a whole lot of people do it, too." I bent down and kissed her shoulder. "Why the question about anal sex?" I hoped I knew what her answer would be and found myself holding my breath while I waited for her answer.

"Well...um...when you...when you...ah...play with me down there, between my legs and all...I...um...noticed it feels really neat when you rub my...uh...anus...with your fingers," she explained.

"Oh," I said. My fingers continued their journey over her silky flesh and I hoped she couldn't feel them trembling. My erection felt as if it had gotten as hard as it could possibly get without exploding.

"And...I...I heard people talking about...you know...anal sex. One of my friends claims she did it and she says it feels fantastic. Anyhow...you're so gentle and all...I thought...um...maybe...you and I...we could..." she laid there, eyes wide as saucers, gazing at me.

"Hillary, are you saying you'd like us to try having anal sex?" I asked, wanting to be sure I wasn't hearing what I wanted to hear.

She nodded. "Yeah...I...I think I...I'd kinda like to try...if...if you want to," she whispered. "Do...do you want to?"

"I want to do anything that makes you happy," I told her. "But you need to know we have to be careful. I don't want to hurt you."

"Does...does it hurt?" she asked, sounding scared and showing a little fear in her eyes.

"It doesn't have to," I told her. "But we'll need to be careful. The last thing I want is to hurt you. It shouldn't hurt if we use enough lubrication and you're relaxed enough."

"Oh," she said, but the fear didn't totally disappear from her eyes.

"Hillary, I promise I won't do anything that hurts you," I told her. "I'd never do that."

"OK," she said. This time she didn't look even the least bit scared. "So we can't do it tonight, then?"

I grinned and shook my head. "No, not tonight. I'll stop at the pharmacy and get the things we need for tomorrow night." I paused. "If you really want to do this."

"I...I do," she said. "We can make love the regular way tonight, though, can't we?"

I chuckled. "Of course we can." I'd never stopped trailing my fingers over her body and kept doing so. "Spread your legs a little," I told her, and she did. My caresses moved to the inside of those gorgeous columns of flesh. I shifted position and spent a considerable amount of time working on her feet, then I moved up to her calves. It didn't take long before she was making the soft moaning sounds of arousal again. I allowed my caresses to move slowly up her legs, to the backs of her knees. "Oh, God, does that ever feel good!" she groaned. "I love the way you touch me."

"I love touching you," I told her. My caresses moved still further upward, to the baby-soft skin of her inner thighs. I've always loved caressing women - at least the few I've made love with - on their inner thighs. The skin there is so soft and sensitive, and it seemed even more so with Hillary. The longer I caressed her there, the more visibly aroused she became. Her hips were rocking gently and she was gasping and making nonsense sounds as my fingers drifted lightly over her ever-so-soft skin.

As my caresses moved closer to her vaginal area, which I could already see was glistening with the juices of her arousal, I had an idea, one I thought might give my young lover a special thrill. My fingers traced over the area where her legs and body joined, dangerously close to her labia, but not touching them. She groaned and the motions of her hips got more pronounced. I let my fingers drift up, over one buttock, across her lower back, then down over her other buttock, back to the junction area on the other side of her body.

"Oh, Jesus, you're making me crazy!" she moaned.

I trailed a single finger around the verge of her labia, downward, and rubbed it gently over her engorged clit. "Oh, God! Oh, yes!" she whimpered.

She was dripping wet and her lubricant covered my finger. I slid it up between her labia and her body rose, as if it couldn't bear to lose contact with my finger. Through her need-slick gap my finger moved, then it slid onto the little gap of skin covering between her vagina and anus.

"Ohhhhh!" she moaned and her hips jolted, when I teased her tiny nether bud with my lubricant-coated finger.

"Unnnhhh!" she moaned when I slid my finger back down to her vagina and gathered more lubricant. "Ohhhh! Oh, God!" she whimpered when I resumed teasing her anus. I circled the tiny bud, then rubbed my finger over it and my actions produced wild responses from Hillary.

While my left hand was toying with Hillary's magnificent butt, I slid my right hand under her and began teasing her clit with the fingers of that hand. By now her hips were moving up and down so fast it was almost as if she was vibrating. Out of the corner of my eye I could see her hands tearing at the sheets and blankets on the bed. Then she stiffened and her body went into what looked a lot like a seizure.

"Ohhhh!! Oh, God! Ohhhhh!!! Oh, Godddd!!! Oh, yesssssss!!! Ohhhhhhhhh!!! Ohhhhhhhh!!!" she screamed.

I kept toying with both her bottom and her clit until moans quieted down, her body relaxed, and she sank onto the bed and laid there, gasping for breath.

"Oh, Jeezum! That was so awesome!" she murmured.

I slid my hand out from under her, stretched out on the bed next to her, put my arm around her, and planted a gentle kiss on her cheek. "Did you like that?" I asked.

"Oh, wow! God, it felt so wild to have you playing with my butt!" she exclaimed.

"It did seem as if you liked it," I responded.

"Liked it? Oh, wow! That was one of the best orgasms I ever had?" she replied. "Are we really going to do it that way?"

"We will if you want to," I said. "But I want to take it easy so I don't hurt you."

She rolled on her side, pressed against me, and kissed me. "I know you won't hurt me," she said after the kiss ended. She reached down between us and grabbed my erection. "What are we going to do about this?" she whispered.

I kissed her. "Well, I was thinking maybe we could find someplace to put it," I responded. I slid my hand down and teased her slippery vagina with my fingers. "Is there room in here?" I rubbed her clit with the tip of my index finger. She gasped and squirmed.

"Uh...huh," she murmured.

"You want to put it there or should I?" I asked.

"Me...um...I...I'll do it," she responded. She pushed me onto my back and straddled me. Then she lifted her hips, placed the tip of my erection at her opening, and lowered herself onto my swollen penis. "God, I just came and I feel like I'm gonna come already!" she exclaimed, looking surprised. Her hips started rocking slowly and the look of lust I loved seeing softened her features again.

"Come if you want to," I told her.

"Are...are you close, too?" she asked.

"Not yet," I told her. "But that's all right. Go ahead, baby, let go. Come for me."

"But...but I..." A look of confusion formed on her face and the movement of her hips grew more and more frantic. "Oh, God! I...Oh, God!...I can't wait! I gotta come! Oh, shit, I gotta...Ohhhhhhhhh!!! Ohhhhhhhhhhhh!!! Ohhhhhhhhhhhhhhhhh!!!" Her body went into wracking spasms and I felt her vaginal tunnel caressing my embedded shaft.

When her peak passed she fell forward, lying atop me with my arms around her, still breathing hard. "What...what about you?" she murmured. "You...you didn't..."

I rocked my hips upward, thrusting deep into her. "You don't mind if I do this, do you?" I asked.

"Oh, God, no! That feels so good!" she murmured in reply. "Don't stop! God! You know how much I like that!"

I grabbed her butt and kept rocking my erection up into her. The increasing intensity of the sounds she was making and the way her body was moving more and more urgently against mine told me she was getting close to another orgasm. I slid my hand over her bottom, picked up some lubricant from where our bodies were joined, then I probed gently at her anus.

"Oh...Oh, yessssss!" she moaned, her body jolting against mine. "Again! Oh, God. Ben! I'm gonna come again! Oh, shit, I am coming again!! Ohhhhhhhhhhhh!!! Ohhhhhhhhhhhhhh!!! Ohhhhhhhhhhhhhhhhh!!!"

"Me, too!" I groaned in reply as my insides uncoiled powerfully, sending a gusher of my fluids into her.

We laid in each other's arms, with her atop me, for quite a while after we finished, letting our bodies calm. Hillary giggled when my softening penis slid from her, but she didn't move off me. I hated the fact that, before too much longer, she'd have to go home. During the first weeks of our relationship I'd gotten too accustomed to having her lying next to me all night. I slept in the bed - and bedroom - that had become "ours". I knew I had gotten far too fond of my teenage lover. Was I in love with her? Probably, if it's possible for a man to be in love with two women. Because I was still in love with my wife.