First time Nipplegasms and Anal for [M]y [F]avorite MILF

My apologies if this is long, but its been a while since I was able to be with my fuck buddy.

Early last year (2019) I started having a pretty hot and heavy relationship with a co-worker. Lena was a Sales Rep for my last company, and I was leading a team of Technical resources that supported them. We hooked up early in the year, and we never stopped. Sales Conferences, trade shows, and even business trips to visit customers. She lives in Boston, and I am in Florida, so it was at least a once a month type thing, and sometimes twice a month. We always made sure to have a night to ourselves, in whatever town we were in, and fucked our brains out. She is a gorgeous woman. Tall, huge tits, sexy curves, and a tremendous, luscious ass. From the beginning this was a primal sex thing. No matter how often we hooked up, the drive and the fire is always there. She is easily the best sex of my life. Such a giver and always open to explore, we have had so much fun. Neither of us are spring chickens, both in our 40s, but when we are together we fuck like teenagers. Its totally intoxicating, and I am 100% addicted to her. It hasn’t gone past sex, because she has kids, and a real life and so do I. But, what she give me is a total escape. An escape into a sex bubble of pure debauchery.

Fast Forward to 2020 and we are still going strong. She took a new job with another company, and it turned out that she was covering accounts in the same territory. So although we weren’t working together, we could still find reasons to be in the same town. I saw her in February and it was awesome, as usual, but then Covid hit. 1st I get laid off, and I was lucky to find another job. Once I was onboard, my company put a travel ban on, and we all worked from home. Lena and I were put on hold. We still Sexted and did some Zoom calls, but it wasn’t the same. We waited for it to blow over, but it never did. After 6months, we were both going bonkers, we were debating driving half way and meeting somewhere in the middle. An alert I had set up on a travel site, sent me a notice on flight deals. I mentioned it to her, and since I was working from home, I could work from anywhere. I said I would fly to Boston, and she offered to get us a hotel. I let her know that she didn’t need to do that, but she was insistent. To get the best deal I had to fly on Sunday, and then return on Thursday. We were super excited to get spend so much time together. We both took Monday off, so we had all day, and then had to work through the other days, but we were stoked.

Finally, the it was time to go. I headed to the airport, mask and all, and I flew to Boston. 2 hours later, Lena met me up at the airport, and we melted into a kiss. I wanted to take her right then and there, but we decided to get to the hotel. Lena had picked a hotel about 30 mins from the airport, and in the opposite direction of where she lived. We didn’t want any distractions. Along the way, we talked about how much we missed each other, and how happy we were to be together. She had checked in earlier in the day, and did some cleaning just to be sure all surfaces were clean. So, once we arrived we went right into the room. Stripping out of our clothes, we were naked in no time. We spent the rest of the evening getting re-acquainted with each other. I spent an hour going down on her and just pleasuring her to multiple orgasms. She fucked my brains out, and then after a fun shower, she returned the favor with an hour long mouth hug for me. The long day, and the excitement overwhelmed us (me) and we fell asleep. Knowing that we had more days together, took the urgency off and lifted the pressure to perform. We were finally able to just be our naked selves.

The sun broke through the window, and Monday morning was here, this was to be a day of firsts. My morning wood was raging. She reached over and commented about it being her favorite alarm cock. Lena gave me a few strokes and then turned to face away from me. Her hand pulled me closer into a spooning position. The light from the window shown down on her, and I had to snuggle up close and feel her all over. I spent some time, just touching her, and enjoying her curves. The whole time she was pushing her ass into my cock, and I knew what she really wanted. My hand worked my way down to her clit, and her pussy was soaking wet. I couldn’t wait anymore. I pulled her to me and kissed her. Then I needed to feel her on top of me. When she rides me, its either a frantic, bucking out of this world romp. Or, my particular favorite, is the slow sensual grind. She has this amazing clamping move that she does, that is excruciatingly erotic. My hands are free to feel her heavy tits and she often leans over to kiss me, or let me suck on her nipples.

Lena threw her leg over me, and she eased herself onto my cock. I was happy for the sex we had the night before, so she could take her time, and I could last as long as we needed. She put her hands on my chest, looked at me and smiled. A satisfying grin came over her, as she closed her eyes. I love watching her fuck me. She sat on my cock, and just let me fill her up. After a while she began her slow mo twerk. I was in heaven. My hands found her hips and I kneaded the softness. I reached around to her ass and grabbed two big handfuls. Slowly her movement went from front to back, to a circular motion. Her pussy bathed my cock in warm wetness. I slid my hands up her back, and she leaned forward. Her eyes still closed, my mouth found her right breast. I took her nipple in my mouth and sucked it gently. My reward was a full mouth of soft flesh with a hard nipple right in the middle of it. I licked her, and pulled her closer to me. I realized she stopped moving. Her moans told me she was enjoying my mouth, and so I kept going. Normally, I like to pay equal attention to her breasts, but for some reason I needed to stay where I was. My tongue flicked and caressed her, as my mouth kept a constant suction. By this time, I had sort of sat up, and she had wrapped her hands around my head, holding me to her chest. I pulled the pillows behind me, and I was able to stay connected to her. I picked up the pace on my flicks and I could hear her moans get louder. Her breath was steadily rising and her pussy squeezed my cock, like a vice. I had her whole nipple in my mouth, and I could feel the areola just past my lips. For some unknown reason, I decided to use my teeth in a soft biting motion. Never opening my mouth, or losing suction, but open and closed pressure with my teeth, matched the timing of my tongue. Her hands pulled me tighter to her chest and she let out a slow but loud moan. At almost the same time, her pussy started pulsing and a rush of hot liquid soaked my cock. I could feel her moisture trickle down to my balls, as I felt a stinging stream roll down each testicle. She got louder, and then took a huge breath in. She hugged me close, the pushed me back looking at me with a shocked expression. Her beautiful smile took over, and she kissed me deep. Pulling back, she said “oh my gawd, I just came so hard. Your mouth put a jolt of lighting from my nipple right to my clit” I smiled back. “I noticed. My cock and balls are totally flooded” She laughed and rolled off of me. She went to the restroom, and came back with warm wash cloth and wiped me off. We giggled as I pulled her down to me, and we laid in an embrace.

While she was in the restroom, I noticed that the bag of sex toys she brings was open, and she had arranged them on the night stand. Along with bottles of lube and massage oils, she had a wand, a butt plug, a cock ring with a vibrator (my fav) and a life like dildo with balls on a suction cup. We jokingly call that Suction Guy. When we are apart, she’ll send me sexy pix of herself playing with it. When we are together, I like to fuck her with it, while she gives me one of her long sensual mouth hugs. The wand is her fav, as it always makes her cum. I like using it on her clit, while I fuck her, it never fails to give us both a charge. Now, the butt plug has been in the bag a while, but we have only used it once before. As our encounters grew, we always talked about different and new things we always wanted to try. She was an anal virgin, and had done next to zero ass play. I had done it before, but didn’t have any strong feelings about it either way. We figured a butt plug was a safe first step, and we would see where it goes. The main thing that attracted me to her in the first place are her massive juggs. She is a 42DD and there is so much cleavage I could get lost. But, since we started hooking up, I have become an ass man. Her ass is so round and yummy. Although it had been in her younger days, you can still feel the firmness of a field hockey athlete. Her ass won’t quit, and she is stupid thicc. I like to fuck her from behind while she lays on her stomach, but her ass won’t let me get too close. My cock is only so long.

We laid in the bed sharing pillow talk, and she explained that she had never cum from nipple play before. She was shocked, but happy. She lay on her back and as she was describing the sensations, I figured I’d play with her left breast as I hadn’t given it any attention. I pulled her to me and I took her left nipple in my mouth. She let me suck on it for a while, and then my hand found her ass. I pulled her more towards me, and she laid on her stomach as I moved to my knees. I grabbed some oils and I worked it into my hands and started to spread it over her back. She spread her legs, and put her hands under her head, and got comfortable for a massage. I rubbed her back and massaged her body, using the oils to let my hands glide all over her. Of course, I worked my way down to her ass. I roughly kneaded and squeezed her cheeks, but the oil only allowed for a playful grip. I slapped and smacked her ass, she loves how I spank her. I traded pain for pleasure and I could feel the heat coming from between her legs. I had straddled her left leg, and my knee was in her crotch. I tried to grind her with it a bit, but that wasn’t enough. My cock was rock hard, and I knew I wanted to fuck her.

I kept one hand on her ass, as the other reached for the lube. I was originally thinking about plugging her, and fuck her pussy. But when I reached for lube, a devilish idea came to me. I had been staring at her asshole while I had been massaging her, and I decided I wanted to take it. I poured some in my hand and stroked my cock with it. Next I put a good amount directly on her ass. I took the opportunity to smack her ass with my cock, and using the lube, to glide it between her cheeks. I leaned forward and said to her confidently “I am going to fuck your ass.” She whispered a husky “ok” and I took my cock in my hand. I put the head right on her opening and slowly drew some circles. I put a bit of pressure and I could feel her relax. More pressure and I could feel it give way, and sort of suck me inside. When I tried to enter, I wasn’t smooth enough and I sort of glided off to the side. Using my hand I re-positioned my cock, and went through the same pattern. Slight pressure with my head, and she was still relaxed. This time, I kept my hand in place, and guided it in a bit more. I felt the head pop through, and in one slow motion stroke. I was fully inside of her. I heard her gasp, and I tried to stay still. I asked if she was ok, and she gave a quiet “uh-huh” I put one hand on each side of her, and lowered myself onto her. I had my mouth by her ear, and I whispered to her. “My cock is in your ass” and I asked “how does it feel?” She didnt answer but let our a long “mmmmm” I slowly moved my hips, and gently thrust in and out of her ass. I was being as gentle until I felt her body really relax, and I picked up my pace. Not fast, and hard, but medium and purposeful. With each downward thrust, she moaned or gave a small grunt. Her ass was so tight on my cock, and I was worried I hadn’t used enough lube. I got close to her again, and I was washed with a warmth. I love being close to her, and now we hand nothing between us, and my chest was completely touching her back. I laid my head on hers and told her how good she felt. She asked if I was going to cum in her ass, but I said I didn’t know. She said “You can” and that was all I needed. I gave her a few more strokes, and my cock swelled up so big. I was going to cum, so I did what came naturally. I shoved my cock as deep as I could go. Loving the feeling of having her ass cheek caressing my whole shaft. My balls mashed hard against her. Then stillness and closeness. A pulse passed and my cock erupted inside of her ass. My balls shot ropes and ropes of sticky cum deep into her, and I came so hard and so good. Breathless, I laid on her and kissed her cheek. I could feel my cock getting soft, and I pulled myself out with the same plop I felt as I went in. She gave me a happy moan and turned to look at me. She smiled and I asked “shower?” She pushed back and we went to rinse off.

So much more playing and exploring were to come in the next few days. But she had given me her anal virginity, and I had given her the first of hopefully many more, nipplegasms.

Source: reddit.com/r/gonewildstories/comments/jqrj04/first_time_nipplegasms_and_anal_for_my_favorite