[F]35 post first normal nude and it leads to [M]42 taking my Anal Virginity (Pt 2)

I heard him call from the bathroom, “head to the bedroom at the end of the hall and we can just play there.” So I jumped up off the couch and walked past the bathroom doing my best stripper walk impression and wandered into his bedroom, that had a large King size bed in it. I looked on the nightstand beside the bed and smiled, there was a good sized bottle of Astroglide on it. I then pulled the covers and hopped up on the bed with my butt up in the air and face down on a pillow making sure he got a good view of my dripping wet pussy and tight virgin ass as he walked into the room. Almost as soon as my head hit the pillow, I heard “Damn! Looks good enough to eat!” I let out a loud giggle at the comment and immediately felt him climb up on the bed and his hand grab the cheeks of my butt and spread them apart. Then I felt his tongue dive straight into my pink pussy hole. His tongue felt so broad and it felt like I was milking it. He slid his hand under my pussy and between my legs and found my hard clit very quickly. Not long after this treatment and him alternating between tongue fucking my pussy and licking and sucking my clit I started to orgasm with his tongue in my pussy. After I finished riding the waves of my orgasm I felt him slide his tongue from my pussy and up my perineum to my butthole. The only other person to do this was my best friend who did this occasionally when we played. I felt his warm tongue licking my butthole teasing it and making it very wet.

As he was doing this he continued to play with my clit and then I felt pressure, he was trying to stick his tongue in my butt! I tried my best to relax and grabbed the sheet by my knee in anticipation and I pushed back against his tongue and “Pop”, his tongue slid in. Of course his tongue was much wider than my finger or his but this felt different, the wetness and texture made it almost enjoyable. He did this for a few seconds and withdrew his tongue and asked “How’d that feel!?”. I was panting, it was so intense yet felt so good I told him. He flipped me over on my back and crawled up and kissed me, and I tasted my butt on him. It wasn’t too bad, a little sweet but tasted like my pussy also.
I felt the head of his now hard dick resting against my pussy lips just a little above the entrance. “Are you still clean?” I asked. He assured me he was and had been tested recently due to giving plasma and nothing had came back. “Ok baby, you can fuck me with no condom then.”

I reached down between us and lined the head up with my pussyhole and wrapped my legs around him and pulled him into me. Like I said before he wasn’t as long as my fiance but he had more girth so it felt like he filled me up more. Without much effort he bottomed out in me and started stroking inside my pussy and I was using my Kegel muscles to try to help him along. God this attention felt so good, he picked up pace and was fucking me pretty hard when he mentioned that he was about to cum. That trick with the muscles always helps, I thought to myself. I locked my heels around his waist and pulled him in tight clenching my pussy around his thick dick, pulling his face down towards mine and whispered “Well then cum in me, daddy!”. He let out a long groan and I felt his dick spasm and his balls contract and warm spurt of after warm spurt of cum fill my pussy. After he was done he kissed me again sticking his tongue down my throat and rolled off of me.

I rolled over and put my head on his chest hearing his heartbeat 100 miles a minute and asked “Having fun?”. He laughed and said “Oh yeah!” and mentioned that he had jacked off to my pics earlier that morning a couple of times before and after messaging me. We chatted a little and I was playfully stroking his dick and caressing his balls trying to get him hard again, worrying that if we didn’t attempt anal soon I was gonna chicken out. Once he was reasonably hard, I asked if he was ready to take my anal virginity and he smiled and that he was only if I was. With a big sigh I rolled over to his nightstand and grabbed the bottle of Astroglide opened it and cover his dick in it. Once he was fully hard I asked how he wanted to do this assuming he’d want to do it doggie style but he surprised me and hold me that in his experience that on my side with my back to him was the easiest. So I took a handful of the lube and tried to cover my butthole in it and pretty easily slip a finger in with so much lube.
“Ok baby, lets try.” I said as I presented my butt to him. He lined up behind me angling his dick up towards my butthole and pushed. He wasn’t quite in line and was more hitting the area between my pussy and butthole so I opened my legs a little and used my hand to guide his head in the right direction. I could feel the head of his dick lined up with my little brown pucker and then felt him starting to put pressure against it. I took a deep breath to relax and tried to push back against him to allow him to enter me. I could feel his head start to enter me, and it was more pressure than pain he placed a hand on my hip and added more pressure and I pushed back against him and “Pop”, his head was in and he was still pushing. “Stop! Please!?” I damn near screamed. I had to get used to this thick dick buried in my butt. He stopped and asked if I was ok, and I assured him I was I just needed to get used to it. He took his hand off of my hip and placed it on my boob and started playing with it. I focused on breathing and trying to relax and felt my butt relax around him. “Ok let’s try to continue” I assured and I felt him start rocking his hips slowly easing himself into my butt.
After a long and slow process I felt him bottom out in my butt, wow this was different, and well pleasurable. I felt so full, I can’t think of another way to describe it. I slid my hand back between my legs and started rubbing my clit. “Ok lets try this” I moaned and he slid out a little and back in and then again and again. He took the lube and squirted some on his dick and pushed back all the way into my butt. That seemed to help, after a bit he started lengthening his strokes and moaning along with breathing heavily. I could feel myself getting closer to an orgasm clenching around his dick. Moaning I said, “Hows it feel to be the first person to fuck my butt baby!?” “So.. fucking… tight” he moaned and slammed hard and deep into my ass. “OH MY GOD!” I screamed… “Do it again!?” I quickened the rubbing of my clit, even pinching it hoping I was gonna cum and maybe even bring him to orgasm. He grunted and pulled out a bit and plunged back into me. This time picking up more speed, I grimaced and clenched hard on him, and felt myself pushing him out now. He said that I needed to let him know if I needed to stop, and I almost screamed “Don’t you dare, fuck my butt… NOW!”. Once those words escaped my mouth he grabbed my hips and drove all of his dick into my butt now taking long hard strokes inside my butt. What felt like an eternity later but only seconds in reality I was wracked by an orgasm, greeting it with a scream. I felt him pulse inside me and then felt him plunge back in my butt one last time and stop as he filled my ass with cum.

That feeling was different and the massive empty feeling in my bowels when my butt pushed him free was odd at best. “Can I get a pic with my cum in your ass and pussy?” I rolled over on my tummy and pushed my ass in the air. “Go ahead, but only one.” I said. After he said he was done, I asked to see the pic and it was a pretty good pic with a white stream oozing out of my pussy and a small trickle running out of my butt and down my pussy lips and my poor little butthole looked red and swollen. We cuddled for a minute or three and then i got up went to the potty, cleaned myself up and went to the living room to get my clothes. Feeling a little more randy as normal I took my panties and wiped my crotch with the crotch of my panties and walked back to the room and threw my panties to him. “Those are for you, where is my money?” He pointed to the dresser where there was an envelope and I walked over grabbed it, counted it real quick and asked, “Was it worth it?” He quickly responded “Hell yes!” and got up, gave me a kiss and smacked my ass while I was getting dressed. I gingerly walked to the front door realizing how sore my butt was now and got in the car being greeted by a sharp pain as I sat down. I was a quick ride home and when I got there I ran a hot bath and soaked for a bit.
That was a fun experience all around, and have found out I enjoy anal now. I have started thinking about maybe trying a double penetration down the road. The last time I masturbated I also tried playing with my ass and I enjoyed it this time. Hoping the experience with anal will continue to get better as time goes on. Hope you guy enjoyed this very true story that happened this past week.

Source: reddit.com/r/gonewildstories/comments/cpagas/f35_post_first_normal_nude_and_it_leads_to_m42