My first milf

The first older woman I ever had sex with was my mother's (now former) best friend, Sandy. Sandy was essentially an aunt that I was not related to. The first time I met her, I was 4 years old. She was a fixture in my life. My parents helped her start her haircutting business and our families would frequently vacation together. That brings me to the first time I hooked up with Sandy.

About 2 months after my 18th birthday, the winter before I graduated from college, my parents and Sandy's family went on a vacation to the Bahamas together. The way the rooms were booked, my brother and I were in one room between my parents and then Sandy and her husband were in the room to the other side of ours.

The 2nd day we were on vacation, I got a terrible sunburn. I was of legal drinking age in the bahamas and already accepted to college so my parents really didnt care...until I passed out on the beach and got burnt to shit. haha

So, the 3rd day, while everyone else was at the pools and beach, I had to stay in the room, put aloe on myself hourly, and take a medication that was prescribed to me by the hotel doctor. That afternoon, around 1-2pm, I was sitting in the tub with lukewarm water trying to heal my skin when I heard the key and main door open. Sandy called out "John, are you here?" I said, "yeah, in the bathroom, whats up?"
She said, "I came up to take a small nap so your mother asked if I'd check on you on the way to my room. Can I come in?" I said, "I'm naked." The door opened anyway. I covered myself with both hands and she kind of laughed and talked for a minute or two. Then she said, "I think you need to put aloe on again, dont you? Do you want help?" I said, "No, I think I have it figured out. There's one area on my back that you could help with though. Let me get my shorts on and come out."
She said, "Just stand up and turn around" and she covered her eyes. I did as she asked.

I was so hard so I had both hands on my dick but was unaware of my surroundings. After I turned, I felt her hands on my back with the cold aloe. It felt great feeling her hands on me which kept me hard but I was doing my best to keep it cool. She said, "All done, turn around." I said, "Sandy, I really can't. I can't." She laughed a bit and said, "Why, because of your erection?" I said, "What?!" She goes, "you idiot, look to your right." I looked and remembered the large mirror in the bathroom and just laughed. Then she said, "turn around." I slowly turned and she said, "Let me see." Again, I said, "What?!" She said, "Come on. Let me see." I slowly removed my hands and watched her smirk.

She took my right hand in her hand and placed it on her left breast as she placed her right hand on my dick and softly tugged it. She said, "We don't have a lot of time. I told Joe I was taking a 45 minute nap and then we're supposed to meet your parents at the bar. Want to have some fun?" I said, "Are you serious?" She said, "Let's see how serious I am." After she said that, she pulled her bikini cups off her tits and got down on her knees and put my dick in her mouth. She gave me the best blowjob I've ever received. She swallowed all my cum and smiled at me. She stood back up, kissed me on the lips and said, "This was just the start. Wait til I give you your graduation present in a few months."

In the interest of moving the story along, the rest of my senior year happened, I graduated, and was only a few weeks from going away to school. Sandy and I hadnt spoken about what happened since it happened but at the haircut I had scheduled before I went to school, she said, "hey, do you have a second?" I said, "Yeah, whats up?" She looked at her next client and said, "I'll be two minutes. I have something in my car for him." We walked outside and she handed me an envelope and said, "Open this when you're alone and let me know what you think."

I got in my car, drove away, and when I was in my driveway, opened the envelope. I was shocked. There were four photos and a letter in the envelope. The photos were of her in black lingerie. The whole set up, lace bra, panties, garter, heels, everything - in various poses. They were so hot. The letter had a whole plan mapped out for a hookup including a booked hotel room, a promise to wear the outfit from the photos, and what she wanted to do with me during our hook up. She explicitly wrote that she wanted to suck my cock repeatedly, get on all fours and let me fuck her in both holes, she wanted me cum all over her face, on her tits, and especially in her, and the letter also stated that she would completely understand if I said no but that she'd be devastated given how she has lusted over this. I called her the next day and told her I couldn't wait. The plan was set.

Two days later, it happened. I met her at a hotel about 30 minutes from my house. I was supposed to arrive at 3 but showed up at 230 because I was so excited. As I arrived, I saw her walking into the hotel and called her. She said, "I said 3pm. I am still getting ready. Here's our room number, see you in 30 minutes." Longest half hour of my life.

I walked in and took the elevator to our floor. I was so nervous as I arrived at the door. It was slightly ajar and I briskly walked in and locked the door behind me. I looked up and saw her. I will never forget that view. She was standing in the center of the room, in the outfit from the photos, with her make up perfectly done, and I was ready to faint. We walked to each other and made out passionately. My hands explored her body as hers stayed on my chest. Instinct took over and as I kissed her neck I slowly turned her around so her back was to me. I kissed her shoulders and neck as I peeked at the mirror in front of us. I groped her tits while kissing her and then worked them down her torso and into her panties. She draped her head over my shoulder and I stared at the mirror as I fingered her. She was soaking wet I could feel her hand rubbing my crotch outside my pants She turned her head towards my face and we kissed again and she whispered, "bed" to me so I walked her to the bed and we laid down together. I unlatched her garter and slid her panties down. She was freshly waxed with a fantastic innie. I kissed my way down her body and ate her pussy until she climaxed. I kissed her body all the way back up to her face and kissed her lips again and whispered to her "Your turn."

we rolled over as we kissed and she said, "Did you like my outfit?" I said, "Ill never forget it." She smiled at me and went down on me. I came so hard in her throat. We made out again for a few minutes before I finally entered her. She was on top. She bent over and whispered to me "I want you to cum in me. I want it slow and long this time. You can fuck me like a whore next round." She winked at me and lifted her body back up and slowly moved her hips in unison with me. We both had incredible orgasms. After we came, we took a little break, got some water, and made out again. We were standing naked in the room and she said, "how do you want me this time?" I ran my hand up her back and gently grabbed her neck and guided her into a bending position in front of the mirror. She placed her hands on the desk and said, "Ok baby, and where are you going to cum this time?" I was 18 and watched a lot of porn, I knew where i wanted to cum. I didnt answer verbally though, i just grazed her cheek with my hand as we made eye contact in the mirror and she smiled and said, "sure thing baby." I started fucking her and watched her facial expressions in the mirror. When it was getting close, I said, "I'm ready" and she flew to her knees right before I blasted on her face. After I came, she took it in her hand and put it in her mouth to get the remnants. She looked up at me smiled. I grabbed her hands and helped her up. She kissed me again and said, "Be right back, I need to wipe all this off."

She came back out of the bathroom a few minutes later and said, "Now what?" I said, "Let's go again." She smiled and jumped on the bed with me. I fucked her four more times that afternoon.

When we were finally finished and getting dressed, she said, "This was so much better than I expected. Thanks baby." I said, "I am never going to forget today. I cannot believe this." She said, "I hope not. that would break my heart. Have fun at school hun, hopefully I'll get to see you over the holidays." She kissed me one more time and I watched her walk out the door.

This has been long but the last loose end is why she's my mother's former best friend. Remember that envelope with the letters and pictures? Yeah, my mother found that envelope a few years later when my parents were cleaning out my room before selling the house I grew up in. She went ballistic. I explained to my mother that it had happened like six years before she found the envelope and it shouldnt end their friendship. My mother did not agree. Hell, she didn't talk to me for about 3 months after that discovery.

I regret nothing.

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