Fan Letters 14

Hey, Hey…  Hailey here with XXX fan letters 14; a new set of spicy encounters to share with all of you!

Sofia from Louisville tells us about her photo shoot gift to her husband and Chase from Cody writes to us about smashing his neighbor MILF when she couldn’t pay up for his babysitting services.

I’ve been married to my third husband for 14 years. But I think this one is my forever guy. As the old saying goes, I am aging like a fine wine. You might not believe it, but I’m 56 years young. While I don’t feel like an old broad, I don’t think I look it either. I have a thin frame, a tiny bum, with massive HHH tits. I’ve had a few boob jobs over the years, but I like my big rack, and so does my man. He’s 58 and successfully manages a small business in our town. He had a conference to attend in Santa Barbara, California. I tagged along so we could tack on a few days for a mini-vacation. We have a great sex life, but with our anniversary coming up, I thought I would gift him a sexy calendar of me! I hired a boudoir photographer and asked him to meet me at our rental home on Thursday at 10 am. My husband would be gone all day for the convention, and those guys always do dinner afterward.

When the photographer showed up, he stared at me awkwardly. Then, he asked for my ID. I laughed, and he smirked but didn’t waver from his request. He said, “I know you’re over 18, but I want to see how old you are because you don’t look like you’re 56!” I handed him my ID, and we settled that matter. Then, I changed into a sexy new outfit I got for this photo shoot. It’s lacy, black, crotchless, and there are cutouts for my boobs to be on display. I styled it with a pair of black stilettos, too. I felt so sexy and started posing for the camera. It was a lot of fun letting the camera lens shutter away while I strutted around. I got these photos back a few weeks later and had plenty of time to order my special anniversary gift. If he likes this, I might kick it up a notch for next year’s gift – maybe shoot a video!

I’ve never been what you’d call a “kid person.” I can get along with them, but they’re not my thing most of the time. But when the MILF down the street asked me to watch her kids for the night, well, I really couldn’t say no. She’s a hard-working single mom who had dinner date plans.

The night itself was uneventful. The kids had their dinner and played games while I sat back, working on a paper due the next day, and I was well on the way to making a few bucks. It wasn’t like I had any prospects of anything actually happening; she was out of my league—a stunning blonde with what looked like a great body.

It was past midnight, and the kids were already in bed, so I went to her guest room and laid down. I started drifting to sleep when the door from the garage swung open loudly. I assume she went looking when she didn’t find me in the living room because she quietly opened the door to the guest room I was occupying a few minutes later. She whispered, “Hey, are you awake?” I rolled over and said, “Yeah. I got tired, so I came in here to lay down.” I could tell she had been crying. Even crying, she was beautiful. Tall, fair-skinned, and with eyes that seared into the soul. Her blonde hair bounced off shoulders that stood proud and supported an ample chest that looked at every moment like it just wanted to spring from its enclosure. I shook my head clear and stayed on the couch, trying to let the back hide my obvious boner.

I asked her what was wrong, but she just waved me off, distractedly going through her purse as she asked me how the night went. I was hoping she would just pay me and exit the room since I was naked under the sheets. (I don’t like to sleep with clothes on.)

Finally, as I waited for my payment, she looked up from her purse and declared that she didn’t have any cash. My first reaction was just to tell her to owe me. But just as I was about to tell that, she approached me bedside and pulled the blanket off my bare chest. Then, she slowly moved her hand down over the blanket to feel my growing dick. It didn’t take me long to shut down every voice in my head: the one telling me to go home, the one reminding me she was a neighbor, the one pointing out that her kids were asleep in their rooms. When a MILF makes a move, you don’t question it.

In one quick swipe, she yanked the blanket off me, and my cock sprung to full salute. I just shrugged my shoulders and gave me an optimistic look. She grabbed my girth and dropped her mouth down around it. Licking the shaft, tonguing the tip, and inhaling it with her mouth work. At times, her mouth did ALL the work, which is different because girls my age usually need to use their hands to give decent head. It’s great being with such an experienced babe.

Wide-eyed, I started pulling her dress off, making her smile as my hands caressed her body. Unclasping her bra was like releasing two fat balloons that had been suppressed. When I finally saw her melons drop right before me, they were twice the size I thought they’d be when she forced them into such tight clothes. I let my fingers trace over the edges of her panties, hungrily awaiting to devour what was underneath.

Before I knew it, she climbed on top of me and planted a big, juicy smooch on my lips. It was hot! As we were making out, she moved her hand down between her legs to grasp my cock. She gave it a few swift pumps and slapped it against her opening. Her controlling approach really turned me on. I felt a few more strokes before she dropped her body down on me slowly. It felt like something close to forever before I finally felt her grinding down on my balls, my dick twitching and teasing with each move.

She was in full control of every part of my body and knew it. Her face leaned in and kissed me roughly as she slithered her body over mine. She was experienced in ways I couldn’t have imagined, finding every spot and playing with me like a toy. I must have hit the edge at least three or four times before she turned around, placing her hands behind her, on my chest, to ride my dick in reverse cowgirl position. I pounded away at her moist pussy, but didn’t want her to orgasm too fast.

I rolled her to the side so I could be the big spoon to her little spoon. The way her insides clenched around my shaft drove me wild. I fucked her harder and harder until she was squealing with excitement. I wanted to fuck her doggy style since that’s my favorite position. Arranging myself behind her, I had the best view of the wet pussy and her little brown button. I grabbed her waist and thrust myself in and out with intention.

Normally, I would’ve finished in a minute or two, but all the edging kept me going far longer. She begged me for my juice, forcing me to bang her harder and faster. Yet it still felt like she was toying with me instead of the other way around. After what must have been my longest time lasting ever, I finally laid her down and dumped my seed onto her gorgeous face.

I made it home, but everything was a blur. I kept questioning whether that encounter was a dream or a reality. Then, she texted me asking if I could babysit again that weekend. HELL YES, and I’ll take my payment in sex.

Thanks to Sofia and Chase for contributing to XXX fan letters 14. If you have a steamy, sex story that’s worth telling, send it to us and you may see your story here! Here are more fan letters: