Kate fluffed up the pillow under my head — “Are you comfy? Make sure! That way you can concentrate on what’s important.” She sized me up head to toe as she said this. She had seen me face to face naked like this very much at all. Usually she was behind me and there would be no eye contact. This was so different — to see her facial expressions as she was talking to me.

“You have a handsome penis Andy. It’s a nice size and it has a beautiful shape. The glans has the most perfectly curved contours. It’s really nice!”

My penis was soft and pointing sideways on my belly. I wasn’t very impressed with myself, but I savored each and every compliment that Kate bestowed upon me. I watched her reach for the tube of lube and unscrew the purple cap.

“Andy this lube is the best for what I want to do to you. It’s super slippery. It’ll help keep you comfy so that you are not uneasy or distracted and you can focus on the good feelings. The physical sensations are important, but I also want you to think about your emotional state as we do this and our connection to each other. You need to tell me things. It will help you understand them and make you feel them more intensely if you put them into words. Okay?”

I nodded as I watched her allow the clear glistening goo from the lube tube to slowly creep down her upright index finger from the tip down to the base. I sighed quietly as I watched her preparing it for my bottom.

“You’re going to be tempted to turn your gaze away, but you have to look at me. We’re going to start now.”

I saw her hand go down and disappear between my splayed legs. I gazed at Kate’s calm face and felt the cool lubricant contact my anus. She then started to gently and slowly smear it around in tight circles with her fingertip before bringing it to rest in the dimple of my opening.

“I can feel that the muscles of your anus are soft. Stay relaxed for me Andy. Keep your bottom relaxed.”

She said it in a near whisper and I could feel her steadily increase the pressure. My anus gave way quickly and I could feel her keep going and push all the way into me. My mouth opened at the gentle slithering feeling of her advancing finger slowly passing through my anus. I looked at her as the sensation transitioned to a deeper subtle fullness. Her mouth opened slightly as she stared into my eyes, studying my face for my reaction and clues to how it was affecting me.

“Is it okay Andy? Is it feeling okay for you?”

I swallowed and nodded, “Yes. It feels different this time. Maybe because I’m on my back?”

“Maybe. With you on your back, my finger curls forward towards the front of your rectum and so I may be touching parts of you in a different way. Do you like it?”

“It feels like your finger is more connected to me. Like it’s making me connected to you. I like that. It’s hard to describe.”

“It can be hard to put these things into words, but I think I know just what you mean. I’m going to keep doing this and move my finger gently and slowly. Tell me if you feel anything new or different, okay?”

Looking at Kate’s beautiful face at the same time as I was feeling her finger slowly maneuvering inside me was so intense. I would close my eyes for a few seconds to give my brain a reprieve. Her finger felt so gentle, warm and slick as she slowly moved it in and then partway out, twisting it slowly at the same time. It produced a kind of tickle in my anal passage that while pleasant was always close to being too much for me. As she gazed at me, she seemed to sense this.

“Is it okay Andy?”

I didn’t want her to stop, so I nodded, “Yes. But maybe a little bit slower?”

“Of course,” she whispered. “You tell me how you like it.”

The tempo of her finger motions slowed and I sighed as I felt relief at being better able to calm my mind and keep my composure. Kate glanced down between my legs and then back up at me with a smile and eyes widened, “Oh Andy! That seemed to help. I could immediately feel the tension in your anus melting. It’s so good that you are learning what you need, what works for you, and to communicate it to me. Good job!”

I cold feel my nervousness easing further and became aware that my penis, which had been completely soft and flaccid and flopped to one side, had swelled slightly and slowly twisted and flipped so that it was now oriented upward across my pubic area. It was not an erection, but it was a definite change. I was sure that Aunt Kate saw this too, but she didn’t say anything yet, she just kept the same steady motion of her finger in my bottom. She glanced down to my penis and anal area every so often, but mostly, she studied my face intensely, studying my every breath, every blink of my eyes and any subtle changes in my facial expression. Sometimes I could tell her face would mirror mine. When a pass of her finger felt especially nice, I would open my mouth as I felt it. She would do the same and then close her lips into a smile.

“Is my finger giving you some nice sensations Andy? Are you liking it?”

I nodded. “Yes.” I hesitated to say any more, but I knew that she wanted more from me.

“Have you accepted in your mind how sexual and erotic this is? What we are doing?”

I could only nod at first, but knowing that would not satisfy her, I spoke, “Yes. Aunt Kate.”

She moved up the bed so that our faces were closer, but still keeping her finger well positioned in me and without any interruption of her steady rhythm inside my bottom.

“I know it is for me, Andy. Very much so. Being here like this with you. Looking at your adorable handsome face. Taking in the sight of your naked body. Your handsome penis. You having your legs spread for me to expose your bottom and to let me penetrate you like this. Giving me access to this most private part of your body. Hearing, feeling and seeing you react to what I’m doing to you. Feeling the smooth tightness of your anus around my finger and feeling with my fingertip the warm silkiness inside your rectum as it swirls around deep within you.”

It was a bit shocking to hear Kate say all of this to me so bluntly. Her words rapidly gave me a full aching erection. She saw this and then looking back up at me, spoke again with a more serious tone, “Good. I think we are on the same page. I see your strong erection. Are you feeling an urge to masturbate?”

I was, but I had never masturbated without complete privacy. Doing it in front of my aunt seemed out of the question.

“A little,” was all I could utter.

“Okay, we’ll wait until you’re ready. We can talk some more. I can’t wait to watch you touch yourself and I’m so eager to have you experience pleasuring yourself with my finger up your bottom at the same time. I’m pretty sure you’re going to really like it. Not just the physical sensations, but the whole idea of it.”

That was all the talking I needed to overcome my shyness. What Aunt Kate was saying in her breathy voice was intensely arousing me. I could feel how tight the skin of my penis was stretched from the strength of my erection.

“I think I’m ready Aunt Kate.” I felt I needed her okay to begin.

“Good Andy! Go ahead. Show me! I want to see you masturbate so badly!”

I put my right around my shaft and gasped slightly. I squeezed and then ran my fingers up to the head.

“Do you want something for lubrication Andy?”

I nodded and Aunt Kate reached for the purple capped tube she had been using on me.

“It’s really slippery, so I’m just going to squirt out a drop for you. Too slippery is no good.”

I held out my hand and Aunt Kate squeezed a clear drop that slowly descended to my palm with a long string behind it.

I spread the lubricant on my shaft and very self consciously encircled the shaft of my penis and start to move it up and down slowly. The pleasure was immediately more intense than I had ever experienced. I’m not sure if it was because of I was with Aunt Kate or because of what she was doing to me. There seemed to be a continuous axis of humming warm pleasure from my anus into my rectum and then from deep inside me out through the shaft of my penis to the head which was exquisitely sensitive. I groaned and closed my eyes.

“Oh God Aunt Kate! It feels so good!”

“I can tell Andy! I can tell by the cute little faces you’re making. And I can feel your little anus squeeze my finger with excitement every time your hand slides over the head of your penis! Can you feel that too! Keep going. Stroke yourself, but not too fast. Savor it.”

I did want it to last forever, but the temptation to pump my hand fast and hard was almost irresistible. I took my hand away for a moment to cool down, and then resumed more slowly. Now that Aunt Kate had brought it to my attention, I did feel my anus tighten around her finger each time my hand slid over the head of my penis. I had never noticed it before when masturbating, but the presence of her finger in me made me aware of every contraction. It was a little embarrassing that I couldn’t really control it unless I stopped stroking myself. It happened at the end of every stroke even if I tried not to let it happen. It was another instance of being with Aunt Kate of having to relinquish some control of my own body.

“Okay Andy, I’m going to try something different on you. I’m going to focus on your prostate gland with my finger tip. I think you’ll like how that feels, but it may feel quite different from what you’re used to at first. Here we go.”

I could feel her finger probing around and then a slowly building sensation deep within my pelvis. I could also feel new sensations in my penis and a sense I had to pee which quickly intensified.

“Aunt Kate, I have to pee! Can you please take your finger out!”

“It’s okay Andy. You’re not going to pee. Relax. That sensation will subside.”

In a few minutes, it did start to fade just as she said it would. It was replaced my a warm full pleasure that was coming from deep within me. From a place that I didn’t even know existed before now. In an instant, I was at the brink of cumming and had to completely let go of my penis to prevent the orgasm. My penis flopped onto my belly and oozed a small stream of fluid clearer and thinner than semen.

“Oh Andy! Did that feel good? Look! You’re oozing some precum. That’s so exciting to see. So sexy! You’re going to feel me put some pressure from the outside with my thumb against your perineum.”

I felt pressure behind my scrotum and then more pressure from her finger inside. It was like she was gripping me with her thumb and index finger. The pleasure intensified further. I gasped and involuntarily pushed my hips up off the bed, but her firm grip on my rectum and perineum, kept me still and steady.

“Easy! Your prostate is small, but I found it! I‘m going to work on it some more before I let you start to stroke yourself again.”

The slow rubbing and pressing boosted the pleasure I felt even more. It started to feel like I was going to have some kind of orgasm without even touching my penis. I was grunting and starting to gyrate my hips. Aunt Kate tightened her grip on me even more to keep me more or less in place.

“Does that feel nice Andy? That nice deep pressure inside your rectum! I can feel your little prostate gland getting firm and tight. Your body is getting ready for an orgasm. I want you to start stroking now. Go ahead!”

I eagerly resumed my strokes and started to cum very rapidly. I grunted and yelled, writhing and bucking my hips. Aunt Kate kept her hand in position as I squirmed and it felt like she kept her finger pushed up right against my prostate (now that I knew what that felt like!).

“Aunt Kate! I’m cumming! I’m cumming!. Oh God!!! Uhhh!”

“YES! YES! Cum for me Andy! Shoot out your semen! Oh god! I feel your tight little asshole pulsing and clamping around my finger! YES! Good boy!”

I thrust my hips up in the air and Kate pressed even harder into me. Every muscle in my body tightened and convulsed. I heard a wet fart escape me and vibrate as it passed around Kate’s finger. The semen shot out of me harder than I had thought possible. I could hear some hit the pillow next to me and some warm wetness on my right cheek and my chin with the first two spurts. The next three painted parallel streaks across my chest. The flow then subsided some, but continued and dribbled down my shaft, over my hand and soaked my scrotum and pubic area.

I laid back and slowly recovered my breath. Aunt Kate moved up and had a big grin on her face as she wiped the sweat soaked hair out of my face.

“Andy! That was wonderful! Look at all this semen! You even got it on your own face! What an explosive orgasm. You even farted as you were cumming! I love to see you lose control like that. I’m going to slowly slide my finger out of your bottom. My finger is partly numb from your anus clenching it so tightly as you were cumming. I loved feeling you squeeze me so tight like that! Just rest and bask in the glow. I’m going to get you cleaned