Misc. Erotica MILF Apartments

I stood before her door and looked at my phone, watching the time until it ticked over to 6:30 pm exactly. Then I knocked twice and waited. I heard Milly approach the door on the other side and heard her flip the lock one, twice, three times. Then turn the door handle three times before she pulled it open.

She stood before me hunched over, her tall frame bent, long brown hair hiding most of her features. Her eyes roamed over me from head to toe before she gave a final nod as if I passed her inspection.

“You showered,” she said, not a question but a statement, “and have followed my directions perfectly. Leave the tools in the hallway.”

“Ok,” I said, a touch amused at her odd manner.

I set the tool bag down in the hall and stepped in when she held the door open. As she went through her ritual of turning the nob and lock three times, I took in her small place.

It was decorated almost precisely as I’d imagined, with spare furnishings and minimal color. Everything was in perfect condition, and the surfaces shone as if everything was wiped down daily.

When the door was finally locked, I turned to her, “Where is the problem you needed me to fix?”

Instead of replying, she stood there for a long moment and stared at me, her fingers twisting together nervously before her stomach. Then she ducked her head, shaking it slightly and walked over to a chair. She seemed to have lost her nerve about something, and she sat for a moment while I stood awkwardly, before she began to speak, her words hesitant.

“I… overheard Gia and Elizabeth speaking the other day about how… useful you’ve been to them… I… wondered if you could provide me with the same… fixing.”

I stood there, stunned for a long moment, unsure what to say. She hid her face from me, and I couldn’t see her expression, but I saw the tension in her shoulders, like a person who expects a heavy blow to fall on them at any moment.

“I figured you might not want to, so I thought I’d entice you with money. A thousand dollars is sitting beside the door in an envelope. Please just take it and go, this was all a mistake, you find me hideous and a freak. I’m sorry.”

For the first time, real emotion bled through her words. I could feel the deep ache of sadness and loneliness in her. It was a twin to what I’d been wallowing for the past four years or more. The anxiety, embarrassment, lack of comfort around others, all of it was so familiar to me that for the first time, I saw a path forward with her.

If not for my time with Ava and Brooke the night before, I might not have been looking for the signs, but I saw them now. Milly’s cheeks were flush, and I could just make out the hardness of her large nipples pressing against her loose top.

I could see the desire plain in her, but also the fear of rejection and self-loathing. She didn’t think she was attractive and had made her belief a reality with her bad haircut and baggy unkempt clothing and posture. With all of that masking the woman beneath, I could still see the brilliance within her, just waiting to be revealed like an uncut gemstone.

Stepping forward until I stood right before her, she was forced to tilt her head back to look up at me, her thick glasses and frames somewhat hiding the pale blue beauty of her eyes. She was a frightened dove, desperate for connection and intimacy but terrified of it at the same time. The confidence and certainty I felt in how to guide her to what I knew she wanted, was a heady feeling, and I found I loved it.

“You think I don’t find you unattractive?” I asked, and when she went to open her mouth to speak, I shook my head, and she slowly closed her mouth, staring up at me with wide eyes.

“I don’t want your money,” I did in truth, but I wouldn’t take it for this, “and if I chose to be with you as I was with Elizabeth and Gia, then it’s because I want to, and because you want to, and nothing else is important.” I reached down and ran a gentle finger down her cheek, she flinched away at first then shuddered as she accepted the touch, closing her eyes to savor it. “And I thought you were beautiful from the moment I first laid eyes on you.”

“Ha!” She scoffed, shaking her head, no and pulling back.

“I think you’re sexy even now,” I said, my eyes roaming down her body, letting her see me appreciate the body she tried to hide beneath her baggy clothes.

“You don’t,” she said, but her voice was breathless, her eyes wide, and I could see the hope in her that she was wrong and the fear of it as well.

My eyes locked to hers, and I reached down and unhooked my belt. She drew in a deep breath and held it. She stared at my hands as they slowly undid each button of my jeans and finally released her breath slowly, as I pulled my hard cock free and out into the open air. Staring at it with wide eyes, her breathing ragged and deep, Milly reached up with one hand tentatively and then dropped it to her lap.

“Touch it,” I said, my tone not commanding but soft and comforting, seductive.

She glanced up to my eyes, then back down to my rigid boner and reached up with her hand again, slowly and tentatively. When her gentle fingers ran down the side, I gave a shiver of pleasure at the cool touch. She started and grinned, looking up at me again, her smile widening when she saw the joy on my face.

Then she seemed to remember herself, and her face flushed scarlet red, and she looked down. Her hand closing around my cock, fingers flexing experimentally. It reassured me that even through her shyness and embarrassment, she never released her hold on my dick.

I stood there, still and quiet, as the woman relaxed. Slowly her head shifting back up to peek at my cock as her fingers flexed on its shaft. Then she ran her fingers up its length experimentally. I let out a soft sigh of pleasure, and she looked up with a small grin, then back down to my dick. Her other hand joined the first as she explored its length. As the second stretched past, Milly relaxed bit by bit, her fascination pushing aside her shyness, anxiety, or whatever it was that she struggled against.

“Wrap your fingers around it… gently…” my voice was a gentle whisper, yet still, Milly startled when the silence was broken. She curled her fingers around the shaft of my cock and bit her bottom lip, “Now stroke up and down the shaft slowly… careful not to pull the skin… yes, just like that.”

I moaned out in pleasure, and Milly shivered in joy, a tight smile forming on her lips as she continued to stroke my cock slowly. She stared at the bead of clear precum that oozed out the tip and pooled just beneath. Beginning slowly and tentatively, she grew more comfortable with the motions and, in a minute, was stroking my dick with soft, sure hands.

I took the time to check her out. Behind the curtain of dark hair, she was quite pretty, with big eyes and thick, luscious lips. Her body was covered with bulky clothing, but from what I could tell, she had some incredible curves.

All I wanted to do was to shove my dick forward, aching for the sweet feeling of her hot wet mouth. I knew that was the last thing I should do, though. Milly relaxed more and more each second, but I could see that the slightest thing could frighten her, causing her to throw her defenses back up. Instead, I stood still, letting the pleasure she was giving, wash over me.

“That feels very good,” I said, my voice quivering slightly as I felt my orgasm approaching.

“It feels so strange… the skin is so soft and smooth… but it's so hard beneath… and it’s… bigger than I thought it would be.” She bit her bottom lip, and I could see she wanted to taste it, but her anxiety rushed in to stop her.

“If you keep doing that, I’m going to cum,” I said as her hand continued to stroke me, causing my toes to curl as the pleasure built and built.

“It feels that good?” She asked in surprise, a pleased little smile on her face as she looked up at me.

“Oh yesssss…. Cumming…!”

She jerked back in surprise as the first jet of pearlescent splooge hit her baggy top, but she never stoked stroking, her fingers tightening, milking my cum out even harder as it shot out again and again.

“Oh!” She said as the cum shot forth.

I was shuddering, my knees trembling, body afire with pleasure as the finally blasts struck her. Milly’s eyes were wide and her breathing ragged as she looked down at her top, running a finger through the cum that drenched it. My cock throbbed in her hand as I saw her bring a finger up to her lips and reaching out tongue tasted my cum.

She jerked back immediately with a grimace in distaste that caused me to chuckle.

“That does not taste good,” she said shaking her head, her eyes never left my cock though, and she gave a little start of surprise when it twitched, “It’s like it’s alive…” she said to herself biting her bottom lip and pressing her thighs together tightly.​