First time ANAL and more [FM]

Him:30
Me:25
Wow what a night
Backstory: a guy, I’ll name him mark, have been talking since day one of Covid shut down (we met on a dating app). We finally met up in august (to be safe from Covid and make sure we were both quarantined and not infected)
At around 3-4 months in, we start talking about having sex, anal never came into the talk. From august to now we have been having bomb ass sex!!! And I always told him I’m open to trying new things!!! As long as there’s communication before hand of what to do instead of surprise toys or acts. We decided to start slowly: create safe words, then we started talking about anal. I told him I’m up for it but I feel more comfortable about talking about it texting wise and less in person. I didn’t wanna text about it for only a split second and then go BAM into it. I needed him to understand the rundown of how it should go down, communication!!!!!!!!!! We finally agreed we would try it in the near future (sooner than later cuz he turns me on and he makes me feel very comfortable). I buy plugs and one helllll of a sexy tail plug.

<<SEXY NIGHT >>
I was prepared for the day and knew it was coming!
I put my backpack together with the plugs in there and had on my sexy tingerie underneath my dull clothes and headed over at noon. Every time I go over I never wanna bam straight into sex, I like waiting a lil and build up the momentum especially if it’s special like building up to your first anal sex! I got there and we instantly watched a Disney movie (we’re both Disney lovers).

<<Normal sex starts here>>
There’s always that moment where netflixing will take its toll and turns into chilling! Low dirty talk while watching turns into massages. My neck hurt all day so he decided to give me a back massage, he slowly took my bra off and panties off (we both watch Netflix in his bed while wearing undies). I knew where this was headed, we tend to always give massages as a hint hint to sexy time. I was laying on my stomach, having such a tiny figure and feeling his biiiig man hands rub oil all over my back, he brought out one of those gorgeous back massagers/vibrator on my back, I knew what he was also trying to do~relaxing me knowing he wanted me to bring out the tail for me to wear and get used to for god knows how long until I was ready for the real thing. This was my first time having anything to do with anal, but I was sooo prepared and wasn’t scared or embarrassed because god dammit this is the most mature person I’ve ever met! I went out the room to get the plug tail and positioned myself on all fours on the bed with my elbows supporting me and raising my ass to his view. I’m happy it was dark because I’m still timid of by ass hole presentation but I feel that’ll go away!!!! I clenched the sheets hard and moved my head between my arms ready! He bent down telling me to breathe in and out and just relax. He took his sweet time with me and he made it special for me! He rubbed my back some more and told me if I was ready and I whimpered and curled my toes and nodded “yes daddy”. I felt the cold lube drip on my ass, I reached back for his leg to let him know I still needed his guidance, rest assured he held my hand for a bit but had to let go to spred my cheeks open and insert the cold metal plug into me, he was so sweet for taking his time, I moaned basically the whole time he was trying to insert it. It took about 20 seconds for him to put it in. I was so proud of my slutty self for being brave to own up to my dirty side. The wild slut was starting to come out of me. I knew in a lil while I was no longer gonna have my ass virginity (unless you call a toy doing the virginity ticket then…) he let me stay there for a bit to get comfy. He let me then relax back in his arms to finish the movie with the tail still in, I fucking love the tail. When the movie ended he decided it was time to be double pentertrated. I scooted next to the edge of the bed while he put on a condom (I have a weird contraception period, I’m still safe from babies phew) but I didn’t want him to be all bloody, he honestly doesn’t mind but for me~ please put it on. He inserted himself slowly into me with the tail in me and by god holy shit it feels tighter for him and me!!!!! He fucked me good while I was in pencil position and him on top, we went at it for about 10ish minutes until he brought me to doggy positioned and pounded the hell out of me! He loooves when I talk dirty to him and he litterally rabbit paced fucked me! I told him how fucking big his cock was! How I was becoming an anal slut for him! How much I love my cunt being full! He plowed into me and told me he was gonna cum! He plunged about 3 big times before he blew his load into the condom in my pussy! I felt sooo fucking dirty and loved it! The innocent lil girl was starting to drift away from me, slowly! And I knew what was next!

<<intermission and break>>
??
Once the movie was done I was starting to get uncomfortable with the plug in my ass. About 10 minutes later I didn’t feel comfortable taking it out on my own, asked him to help and he didn’t even blink, and helped me without being grossed out. I cleaned the toy then we both took a breather and I studied for my classes and he played video games and then we ate from door dash. Ehhh about an 2 1/2 hours later I left from the couch and sat next to his feet, the floor felt better than the couch, my neck was killing me and nothing could help the pain. About 7 minutes later he got up and swayed me to get up, he scooped me up like I was a princess, which i always fall head over heels for!!!!! Prince move!!!!. He carried me to his bedroom, 10 step away….

<<ANAL SEX PREP>>

I knew this was going to be the chapter of the day where it was gonna happen! It was like…..4 o’clockish??? (Who knew what time it was, we were having so much fun) we decided to cuddle again but clothes on (both cold). We watched a mature movie this time….it wasn’t even 30 minutes into the movie and we couldn’t control the heat between us! We kept talking dirty of how proud I was with having the toy in my ass! He praised me like the good lil anal slut I was becoming!He asked if I was ready and I nodded “yes sir”. He got up off the bed and took off his shirt and layed down a huge shower towel below me. He talked dirty for me which helps me get in the mood. He knew the plan, talk dirty, coach me, and massage me to relax my muscles and anxiety! He rubbed my back while i was on all fours crouching with my elbows once again supporting me, with my my ass for display. This time no condom! I told him if he was sure each time we talked about it while texting and he had accepted to not being grossed out~ (huuuuge props for a guy who’s just sooo mature!!!!!). So him whipping out his bare cock wasn’t a surprise and I was ready for the next step…..

<<ANAL SEX TIME>>

By the time I told him I was ready, he immediately turned off the movie (he doesn’t do that when normal fucking) I assume because so he can hear me say RED (safe word). And to fully hear commands and communicate throughly. It doesn’t help when there’s access noise while trying to do somthing that causes anxiety. (I suggest being in a quiet room helps with lowering stress for anal sex readiness)
The moment has come, he told me if I was ready and I said “yes daddy”. He lubed up my ass hole and I felt a finger go in gently, he massages my ass cheeks and I could hear the sloshing of the oil he was putting on his dick. I immediately ran my hand back to try and find his hand for guidance and comfort but knew it was on my ass and one on his dick. He lowered down and told me that “everything will be ok, just take it”. He knew I wasn’t ready for the dirty talk yet, just comfort and coaching me I was doing great. He enters in and his head wasn’t even all the way in and I opened my mouth to shudder but no noise came out. He told me once again to relax, breathe in!!!!! His voice was like warm chocolate, it was comforting and beautiful! He had a lil bit of a hard time going inside my virgin ass but he kept trying. I then told him to go in and come out, go in and out, in and go out, go in etc….it worked. He went in and I muffled my face in the bed and grabbed the sheets sooo hard. I scooted away and got him to come out~ not even the whole head was in, I layed there ina pencil pose, he asked if I was ok and I kept thinking to myself “give this a real try!!!!!!!!!! This isn’t the best you can do!!”. I positioned myself back on all fours this time, full doggy position, no hiding my face. He once again entered, success, I was expecting myself to cry, but no! I kept asking “how much went in now?”, I felt proud when he told me The head was all the way in, 2/5 in, half way! I was then 3/4 in! He went gently in and out in and out to get further into my ass! I couldn’t believe I was doing it! I was no longer a timid girl! I was ready to meet the base of his dick! It felt like forever. And I was afraid I would be….”full” if you know what I mean. He finally made it to the base and I felt alright! I had a tear in the corner of my eye not from the pain~ but 6 years of boring sex from exes and I have now committed myself to the most slutty actions I was happy and proud! He let me stay there for a moment until I told him to start moving. He started moving a lil too fast for comfort and I told him to sloooow it down. He obliged and carefully came in and out, not too much moving in and out~ this is still my first time. I then began to really start moaning. My small 36c tits started flapping around and I felt like such a slut! I kept telling him how big his cock was in my tight ass! He reached below and massages my pussy and brought out the vibrator for both of our delight! I couldn’t focus on that when his dick was railing my ass! I positioned it behind his balls and I could hear him moan. He moaned telling me he liked my tight ass! “It’s sooo right! It’s sooo good! I like fucking your lil asshole”. I liked the dirty talk about my ass hole! Better than regular sex talk! We didn’t re-lube his dick because the amour had sufficed the whole time! He plunged into me the way he did but a lil faster but with small lengths. I felt myself sweat way more than usual sex and I didn’t do any of the work! I kept going downward dog pose and back to doggy position where his chin would rest on my shoulder and I could feel his cheek on mine and he would kiss my cheek and whisper and moan in my ear from behind. I looked behind me and I could see a sling of light bouncing off our skin and could see the oil glistening off our bodies that were touching! It felt like a movie scene! It was fucking hot! After a while my ass was getting sore and I knew it would be hard for him to cum since he had already came earlier, this was more of an experiment of trying anal! Not to get to orgasm reach~ that’ll be next time or the time after that, When my ass hole is actually comfortable with his width and won’t get hurt. He was still inside me until I told him I was prepared for him to come out! The only thing I was severely worried about was him coming out and farting and maybe somthing else would come out, I prepared my ass hole to close up once I felt the tip come out…I couldn’t nor wanted to clench my asshole while his whole width was inside me~ it hurts! He finally came out and he was ready with a towel, i was saved by my preparation that the evacuation went smoothly. He ran into the bathroom and showered in the dark (he always does that)…I don’t blame him, I wouldn’t wanna…ya know. I followed along
behind him and showered and cleaned ourselves!

<<More sexy stuff>>

We once again relaxed in bed with lights out. And the bathroom light on as a “night light”.
I told him once more of how happy I was to actually commit to trying anal! He was happy and a few moments later, the next thing I knew~ he was sitting upright on the bed and I was infront of him and he had his plugged in vibrator massaging my pussy, I directed him where the clit was (dark and he can’t see from behind me) I kept screaming when he hit it and keep moving so much because it feel sooo damn good! He finally had enough of me running away from pleasure that he tangled my legs into his so that they couldn’t move, he places a men’s tie wrapped to make a gag so I couldn’t make loud noises. He bear hugged my front with one arm so I couldn’t move my arms or my upper body, and he controlled the vibratory with the other hand, amazing skills he has! Even though I couldn’t pronunciate with the tie in my mouth he knew my directions with “go right, go up, down, left”. I screamed each time he hit it. He had once again told me to take it! This time no running away! I honestly gave my best effort to accept my fate and just accept the pleasure! He finally gave it one last go and made it on my clit. I had started screaming immediately and less than 9 seconds later I could feel myself coming. This huuuge shock of pleasure ripping and feeling it come out. I told him I was cumming and he told me to keep going, keep going, cum for daddy! I finally came and I started crying! Never has he let me down with pleasuring me! 6 years of boring and unpleasurable sex and I found the guy who can make me cum from his dick and the toy! I cleaned myself off once more and then we layed down naked and had a cat nap until it was time for me to go at 10pm. I told him don’t bother getting up since he was half asleep. He kept telling me he would walk me out but I said no it’s fine. I kissed him good night and drove home and now writing this.
I drove home just thinking that my ass virginity wasn’t there anymore! I was a whole new women! There was no longer an excuse to wait to try anal! I had done it! And I couldn’t wait to try it again! We keep things veeeery interesting in the bedroom~ sexy clothing, skirts, lingerie, toys, collers, leash, now butt plugs! I know my future hopefully with will have more soft Bdsm like toys and actions!

Edit* this was last nights adventure* 10/14/20

Source: reddit.com/r/gonewildstories/comments/jbvt88/first_time_anal_and_more_fm