Pegging my boyfriend on New Years [FM]

For New Years I(20f) offered ideas to my boyfriend(19m) on things to Improve on. One thing I recommended was trying to be more sexually open, not just active. He said he would work on that this new year. I followed up and told him he’s shy about his ass, and what better way to start than with something in his ass.

Our relationship is very trusting and caring and he actually said he would try it. We got boozed up to make him looser and less anxious. I bought this impressive 7 inch strap on from Amazon. It’s a black dildo, not too wide but pretty long, connected to a harness. I figured he could take the big dick and I wanted to see. My sweet sex demon was gonna let me in his ass. Now he’s had gay experiences before but he’s never before let me touch his ass.

At midnight we made out and got to work. He ravaged my clothes off and put his mouth to good use. It felt like he forgot our little mission for the night. I gave him some head while he laid down but after a few minutes I raised his legs and rimmed him. He jostled around surprised but then tried to settle after remembering our arrangement. Don’t worry about cleanliness though, he cleaned via my instructions earlier but I think his drunkenness made him forgetful.

So anyways I start tonguing his asshole which was nicely shaven and smooth, even fresh smelling. He was uncomfortable at first but settled in and was soon holding his legs up so I had easier access to his ass. I found he really enjoyed when I twisted my tongue while it was partly deep in his ass. He was even more pleased when I finally moved to fingers and had a couple curled in his butt while i sucked him off.

He got close to cumming a couple times, each time I edged him away which totally riled him up. I put him to the test because it looked like he wanted to destroy me but was taking the edge patiently. When I was satisfied with fingers I finally whipped out the black strap on. The look on his face was lust and curiosity but also a lot of timid ness to the point it looked he would stop. I quickly talked dirty hoping it would make him more horny and willing to take the dildo. I put it on and crawled sexily to him. It looked like the plan worked because he turned around on his hands and knees to take it.

The passivity coming from him was really unique and hot. He was all submissive and ready to actually let me fuck his ass. It gave me confidence and the balls to talk dirty to him, and kinky! I repeated the same words he’s used on me like “your tight fuckhole looks so hot and delicious”, “I can’t wait to see your tight asshold stretch from my big cock”, or “I’m gonna fuck your brains out little slut (with a hard slap on the ass)”.

He wriggled his ass at me which made me smile and surprisingly turned on. In any other circumstance except drunk he would never let this happen. I let the scene sink in that my boyfriend was being a little anal slut and I had the power to make him orgasm with my dick. I lubed him up with spit and lube and lathered it on my fake cock. I rocked my body and pointed the tip between his asscheeks, I just grazed his asshole and gooche like he does to me every time. When I really tried to penetrate him he took it like a champ. I watched in awe as his asshole gaped around the tip at tightened when it got over the head. I kept his asshole spread with my hands slowly pushed while watching intently.

It was so crazy to watch his ass expand and the dick slowly disappear in him. Even crazier is pulling out and seeing his ass literally stick to the shaft as you pull out. I got to about 5 inches and I felt resistance like it was hard to get the rest in. There was lube and all but I dunno, maybe he’s got a shallow ass or he’s too tight.

I started trying to fuck him but the rhythm is hard. I never really got the hang it of it but it was better in the end then the start. I slow fucked him for a few minutes, also adding a bunch more lube. He was moaning and grunting like a little bitch the whole time. I’d never heard him moan so genuinely and passionately. He was really gasping with a few good thrusts. It really turned me on to hear him so vulnerable and sexy. I watched and felt the dildo pull his body while I was in him, like his ass was so tight he kinda gripped the dildo.

I asked him what he wanted because I didn’t know what to do but awkwardly fuck him doggystyle. He just wanted more, and a little harder. I tried not to go to hard because the rest of the dildo was hard to get in him. However, all it took was a little warming up and elbow grease because the remaining 2 inch gap of cock slowly disappeared. With so much dick to work with I was really thrusting in, working my hips to get it in as hard as possible. Soon I was really slamming my pussy against his ass and I can say it was an absolute blast! I was impressed with my body and checked out my legs and stroke game.

I stayed in doggystlye the whole time until he said it was too much and he need to cum with a blowjob or vaginal sex. I’d rather him fuck me then lick near a clean but well fucked asshole. Without taking the strap on off we changed positions and he fucked me for just seconds before cumming like a geyser. Overall this was great fun and we will absolutely try again. I never got to see his face but next time I think he’ll be less anxious and we can do missionary. It was a clean experience thank god.

Source: reddit.com/r/gonewildstories/comments/korzq9/pegging_my_boyfriend_on_new_years_fm