In the following weeks, Myles grew bolder, sneaking into my room almost every night. I'd begun taking a nap shortly after dinner so that I'd be bright-eyed and alert when he arrived a few hours later.

On a hot night in August, I noticed he wore a sly smile while climbing through my window. I sat up in bed, wearing a pink nightie I'd bought especially for him. Through my own smile, I said, "You're looking quite devious tonight."

"Me? Never!" Myles was quick to close the distance between us. Tilting my head back, I eagerly accepted his kiss. "Have I mentioned how much I love seeing you in that lingerie?" he murmured against my lips.

"A time or two."

"Glad I got my point across." Standing up to his full height, he withdrew a small book he'd tucked into the back of his jeans. "I brought you something."

My eyes widened at the cover art. "Myles! Where did you get that?"

"I've had it a few years now." He pulled his shirt over his head, drawing my attention from the book to his bare chest. "I thought you might enjoy it."

Taking the book from him, I tentatively opened it, as if afraid something would jump out at me. It was full of black-and-white erotic photographs, most of them so explicit that they brought a blush to my cheeks. I guessed many were taken in the sixties, but some were far older. I marveled at the various sex acts and positions.

Once Myles was naked, he joined me in bed. Lying at my side, he seemed to delight in my reactions as I turned the pages. "I really like that one." He tapped a photo of a man performing oral sex on a gorgeous blonde. The man's tongue was extended, just millimeters from her swollen clitoris. I found myself closely studying the woman's pussy and wondering if mine looked similar. I was too shy to ask Myles.

The photos on the next pages made me gasp. In the first one, a brunette with a cute bob hairstyle was photographed in profile. She knelt before a man with an enormous cock, her gaze almost worshipful. In the second picture, she'd taken his entire length in her mouth. "My God!" I exclaimed. "She missed her calling as a sword swallower!"

My remark caused Myles to crack up laughing, and I couldn't resist joining in. But my giggles turned into low moans when he leaned to kiss my neck and fondle my nipples. "Does looking at these dirty pictures excite you?" he whispered. My stare remained fixed on the racy images as I nodded. "It excites me, too."

"I can tell," I said wryly. His cock seemed to be growing harder by the second.

Sliding a hand along my inner thigh, Myles inched closer to my damp panties. All those obscene photos served to intensify the pleasure of his touch. As he slipped his fingers into my skimpy underwear, my breaths came faster. But despite my heightened arousal, I was still shocked by one of the last photographs in the book.

I sensed that Myles had been waiting to see my response to it. While massaging my clit, he asked, "What do you think of that one, Colleen?"

With a shameful fascination, I stared at the photograph. It featured a woman on her hands and knees, with her bottom lifted in the air. A man knelt behind her, and he'd worked the tip of his cock into her ass. Studying the woman's profile, I couldn't tell if her expression was one of abject lust or excruciating pain.

"I think it looks very uncomfortable. For the woman, that is."

"Wasn't vaginal sex uncomfortable for you the first time?" he asked softly.

"Extremely." Though I knew where this conversation was headed, I wasn't yet sure if I wanted to steer it in another direction.

"But now you love it, don't you?" Myles didn't give me a chance to respond before planting a tender kiss on my mouth. "It would be a first for both of us. Something new we could experience together."

Curiosity and apprehension warred within me as I contemplated his words. "I'm afraid it would hurt too much," I finally said.

"If it's too painful, then we'll stop immediately," he promised. "The last thing I want to do is hurt you. And of course, I understand if you'd rather not." He began stroking his hard dick while gazing at me. "But who knows? You might find that you enjoy it."

It was at times like these that I wished Myles weren't so damn persuasive. Again, I stared at the picture, and the woman's intense expression. Did she actually enjoy being taken that way?

Before I could lose my nerve, I said, "Okay, we'll try it." The words spilled from my lips in a rush.

Myles flashed a big smile, obviously pleased by my decision. Though his kiss was tender, I could sense the eager anticipation in it. "We'll need some Vaseline," he told me, "and it's probably a good idea to put a towel down."

Swallowing hard, I struggled not to change my mind. "There's Vaseline in the bathroom medicine cabinet, and you can grab a towel from the hallway linen closet."

Once Myles had gone to retrieve the items, I stripped out of my lingerie. He quickly returned, still wearing that reassuring smile. The sight of his erection let me know just how excited he was for this, and I wondered if it had always been a fantasy of his. I couldn't imagine him asking Dana to try it.

As I waited for him to spread the towel out on the bed, I reminded myself that he'd never forced me to do anything I wasn't comfortable with. Even when he was fucking me hard, I knew he'd stop the instant I told him to. My trust in him was the reason I was now willing to indulge his request.

Lying on my back, with my head resting on the pillow, I took several deep, calming breaths. Myles slid his palms over my bare skin, and his touch served to relax me even more. Soon, I was moaning from the pleasure of his strong hands working the tension from my muscles. When he eased on top of me, I readily slipped my arms around him.

Myles took his time planting kisses on my mouth and neck. Lingering over my breasts, he sucked each nipple until my hips began rocking with clear arousal. As he moved lower, I ran my fingers through his hair. The moment I felt his warm breath against my pussy, I spread my legs wider. My clit was already swollen from his fingers, and it instantly responded to his tongue.

"Yes! Just like that, Myles!" As he eagerly licked and sucked that sensitive bud of flesh, I tugged at my nipples. Looking down at him, I was struck by the fervent lust in his eyes; it still astonished me that he took such pleasure in this act. In the past, I'd been made to believe that so many things were dirty or wrong, and it was Myles who showed me otherwise.

It didn't take long for him to coax forth my first orgasm. By this point, he was intimately familiar with my body and what pleased it most. I made no attempt to subdue my shudders and cries, for he had managed to strip me of all self-consciousness. With him, I was truly free.

When my trembling finally subsided, Myles guided my legs upward. I placed my palms against the backs of my thighs to hold myself open and spread wide for him. Though my nervousness grew as my orgasmic bliss waned, I still felt plenty relaxed. Myles gave my clit a final, teasing lick before sliding his tongue lower. I thought he might work it into my cunt, the way he'd done many times before, but instead, he continued moving downward.

A startled shriek escaped me when he swept his tongue between my buttocks. "Myles, what are you doing?!" Not even his book of obscene photos included such a filthy act!

Rather than stop, Myles began licking and kissing my tight hole. "How does that feel, baby?" he murmured.

To my amazement, it felt incredible! I had no idea that part of my body was so sensitive to stimulation. "It feels good," I finally confessed.

"I'm glad, because I love doing it." Our eyes locked as he continued pleasuring me in such an illicit way. I knew it thrilled him to make me admit I enjoyed something so taboo. My tight flesh was so receptive to his tongue! Though my pussy wasn't the current focus of his attention, it remained sopping wet.

Once Myles had gotten me so excited that I couldn't suppress my needy cries, he retrieved the small jar of Vaseline. I watched as he gathered some on his finger and spread it over his skin. When he brought that lubricated finger to my anus, I nodded to let him know I was ready. Slowly, he eased it inside me, meeting no resistance.

"Does that feel okay?" he asked quietly.

"Yes," I replied, sounding a little short of breath. "It doesn't hurt."

Myles began gently circling his finger, as if to open me wider. Again, I was surprised by the pleasurable sensation of his touch. As my arousal intensified, my moans grew almost continual.

"I'm going to add another finger now," he said.

The moment he did so, I felt a lot more pressure, and I had to remind myself not to tense up. I kept waiting for the pressure to morph into pain, but my body accepted both fingers far more easily than I'd expected. I wondered if it was because he'd made such an effort to relax me beforehand. Both of us were breathing faster while he gently worked his fingers deeper into my ass.

Finally, he whispered, "Are you ready, sweetheart?"

"Yes," I whispered back.

A shiver went through me at the feel of him applying the petroleum jelly to my stretched hole. He also smeared some on the head of his cock. With my legs still lifted and spread, I felt as wanton as one of the women in that book of erotic photos.

Kneeling before me, Myles positioned himself so that his tip was nestled against the opening he'd enthusiastically explored with his mouth and fingers. He moved with utmost care, doing all he could to avoid hurting me. Once more, I felt intense pressure. As he worked his cockhead farther inside my ass, a twinge of pain made me gasp. Immediately, he paused, his stare meeting mine. "Do you want to stop?" His soothing tone served to ease my anxiety, and I shook my head.

"Keep going," I told him.

Myles inched deeper, and I noticed his jaw tighten from the painstaking effort to be gentle. His gaze moved from my face to his cock, and then back to my face again. "Talk to me, baby," he urged.

"Ah, it's..." I struggled to describe what I was experiencing. "It hurts a little, but... I don't want you to stop."

"Are you sure?"

I nodded, and as Myles continued, I discovered that a subtle but unmistakable pleasure was building within me. It mingled with my ebbing pain, leaving me to wonder which sensation would triumph.

It turned out that pleasure won the battle. My cries grew louder, and I was reminded of the woman in the photo. Did my expression mirror the one I'd seen on her face? I now understood how she could appear both wounded and enraptured.

At one point, my muscles involuntarily bore down, as if to force Myles out of me. Instead, it enabled him to slide farther inside until he bottomed out. "I'm all the way inside you, Colleen!" 

My face was flushed and damp with sweat, and I noticed Myles was sweating, too. Gazing up at him, I laughed in sheer relief. "How does it feel having your cock in my ass?"

"Like I've died and gone to heaven!" he groaned. "You're so tight all around me!"

I gingerly raised my legs, and Myles took hold of my calves. "You can start... you know..." I gave him a helpless look.

Lifting an eyebrow, he flashed a wicked grin. "You want me to start fucking you?"

"Uh-huh!" I nodded for extra emphasis.

His thrusts were slow and shallow, not at all like our normal lovemaking, but his jaw slackened from the intense pleasure of it. With each pump of his hips, the stimulation I experienced grew far more powerful. I let out a wail when he dared to drive himself inside me balls deep. Without fully registering what I was doing, I slipped a hand between my thighs to rub my clit.

"Fuck, yes!" Myles panted. "I need you to come for me, Colleen!"

It was then that I realized how close he already was. Normally, he had no trouble outlasting me, but as he'd pointed out before, this was a new experience for us both. Something about masturbating while Myles's dick was buried in my ass made me exquisitely aroused. Once again, pain and pleasure carried on a serpentine dance deep within my core, and I soon trembled from the need to climax.

Looking up at Myles, I saw that he appeared feverishly lot, with rivulets of sweat trickling down his skin. When I tried to clench my muscles around his cock, he actually whimpered.

"Colleen, please! I can't..." 

Finally, I surrendered to my orgasm, and as the first contractions seized me, I could only moan. It was almost too much, the way my body seemed hellbent on gripping Myles's dick. Even as a flash of pain lit up my insides, the spasms continued.

I heard his breath hitch in his chest just before he climaxed with a shudder. Though the groan that emerged from low in his throat sounded pained, I knew better. My own cries were dangerously loud, but I was helpless to stop them. I was shocked to feel Myles's cock pulsing within me as he came hard.

Afterward, he remained inside me for a little longer. Still breathing heavily, I smiled when he closed his eyes and placed a tender kiss on my calf. It was hard for me to believe I was the reason he now looked so utterly satisfied.

Despite the care Myles took in pulling out, I had to bite back a wince. We were both burning up, but that didn't stop him from lying on top of me and lowering his lips to mine. "I can't get over how amazing you are," he murmured while smoothing my hair back from my face.

I grinned up at him. "You're only saying that because you just fucked my ass."

He shook his head, his expression serious. "No. I'm saying that because you're the sexiest woman I've ever met."

His words sent a giddy rush of happiness through me, though I knew he must have felt the same way about Dana at one time.

Once we'd cleaned ourselves up, he rejoined me in bed. Both of us pointedly ignored the fact that it was almost one in the morning. "I think it's a good idea for me to sleep on this towel," I said. "Your semen doesn't come out of my ass nearly as fast as it does my pussy."

He gave me a remorseful look. "I'm sorry I didn't pull out, baby. I tried, but I was so close, and I feared hurting you if I withdrew too quickly."

"It's fine," I assured him with a smile. Lying in his arms, I realized that what we'd just shared felt incredibly intimate and special because I'd given him something he'd never before experienced. Though my ass was tender and would probably remain so for the next few days, I was glad Myles had convinced me to try anal sex. And I already knew I'd be willing to do it again.

"You know," he said in a relaxed, drowsy voice, "Labor Day is just a couple of weeks away."

"It'll be nice to have a long weekend," I replied while nestling deeper into his embrace.

"Dana and I are having a cookout that Sunday afternoon. We're inviting friends and coworkers, and she also wants to invite some neighbors."

I wondered if he felt me grow tense at this news. "She hasn't invited me." I was careful to keep my tone neutral.

"That's because I told her I would," Myles said. "I mentioned that you and I get home from work at around the same time, and I'd invite you next time our paths crossed."

Of course, our paths most often crossed in my bedroom. Grazing a fingertip over his chest, I asked, "Do you really think that's such a good idea?"

"Why wouldn't it be? I mean, don't you think it would seem suspicious if we avoided each other?"

I lifted my head to give him a measured stare. "No. People will just assume you don't like me."

Myles laughed at that. "I could never pretend I don't like you."

"That's what I'm afraid of!" The thought of someone figuring out we were sleeping together was enough to fill me with a nauseating dread.

"Hey, stop worrying. Everything will be fine," he said before giving me a quick kiss. "I want you to know me beyond the walls of this room, Colleen, but if you find you'd rather limit the time we spend together to these late-night trysts, then I'll understand."

I had to avert my gaze as I whispered, "You know I always want to spend time with you."

"Then at least make an appearance. Do it for me, okay?"

Yet again, he exercised his talent of persuasion, and I found myself nodding even as the knot of dread tightened in my stomach. Maybe Myles was convinced he'd be able to hide his feelings while we were around others, but could I trust myself to do the same?