[MF] My first time having anal

I [33F] started seeing Merlin [33M] a few months ago. We had good conversations and went out a few times for dinner or would meet up for board games. When we had sex for the first time it was a little awkward. We’re both very shy and hadn’t talked about what the other person likes sexually. It was still good; in fact, he ate me out like no man ever has before. (More on that later)

We kept meeting up, sometimes we’d have sex, sometimes we would hang out with his friends or just watch a movie. After 2 months of meeting like this, we were reading together on his couch one night and I let him read a chapter of the book I was reading. In this chapter, a dom punishes his sub by spanking her and making her count… you know how it goes. Afterwards he said, “It seems like the guy isn’t a great guy.” So I thought he didn’t like it and wasn’t into any kink, since we had been very vanilla to this point.

A few minutes later we go into his room, and he says, “Spanking may be a little too loud, since my roommate is home.” I didn’t quite know what to make of this. He starts kissing me and undressing me, taking notice of the black lace bra I’m wearing, and I see a hunger in his eyes that I’d never seen before. He undid my jeans and felt the small piece of fabric that was my black lace G-string. He shoves my jeans down my legs and flips me on my stomach so he can see them. I knew he liked by sexy panties and that’s why I always wore them, but his reaction shocked me.

One minute he’s grabbing my ass and almost massaging it, the next his mouth is there, biting me. Coming from this shy man, I didn’t expect it one bit and it made me so turned on. He took my flimsy excuse for panties off and started kissing his way from my ass up my back, to my shoulders and neck. He turned me back on to my back and gave him that look again. Like he’s starving and I’m the only thing that will satisfy him.

He starts by sliding one finger into my wet pussy and curling it so it’s stroking my G-spot. Next thing I know there’s two fingers in. He has me in the palm of his hand at this point. That’s when I feel another finger, but instead of in my pussy it’s in my ass. Of course, this isn’t my first time with this, but it was so surprising coming from him. It keeps driving me higher as he roughly fingers me. He gives me a devilish look because he knows I’m wanting to scream and I’m squirming to meet his hand. He kisses my breasts, sucks on my nipples, and kisses his way down my stomach and even the insides of my thighs. He just barely touched his tongue to my clit when I came, hard. Instead of easing up after that, he only intensified what he was doing. Sucking my clit hard and teasing it with his tongue. Fingers slamming into me until I want to cry out. Having to be quiet because his housemate was in the next room made everything heightened. He doesn’t stop, not until I grab his hair and pull him up to me and I buck him off me.

I dragged him up to kiss me so I could regain my breath for a second, that and stop shaking from being driven so high. I push on his shoulders so he’s now the one on his back and climb on top of him, wanting to show my appreciation for the fantastic orgasm. I rode his dick slowly at first. Gently bouncing up and down, switching from just having the tip in, to slamming all the way down onto him. He’s not a vocal person like I am, but as I watched his face, I saw he’s getting close to his release. I pick up the speed, wanting to see him cum. As he cums I keep the speed up watching the pleasure ripple through him. I finally start to slow the pace and watch him come back to earth before finally removing myself from on top of him.

I roll onto my side with my head on his shoulders and he kisses my head while I gently run my fingertips over his balls, feeling him shiver when I do. We fell asleep in each other’s arms, and I had the best night’s sleep I’d had in months.

I woke up before him the next morning, it took all my self-control to refrain from going under the blankets and sucking his dick to wake him up. I go in and out of sleep for a few more hours until he finally wakes up.

I smile at him, and he smiles at me, pulling my chin up for a kiss. I thought he would want me to leave soon (this was the first time I spent the night and didn’t know anything about how he is in the morning), but he gets on top of me and starts using his magical fingers on me once again. I was still sensitive from the night before so when his thumb even touched my clit, I was arching my back and curling my toes in ecstasy.

There’s no gentle warm up like the night before though, he feels how wet I am from sleeping next to him all night and refraining from waking him up and driving his fingers into me again. Yet again he goes in my ass with his pinkie, has two fingers inside my pussy, and is using his thumb to rub my clit. I cum after only a few minutes, but does he stop? No, he keeps going until I am thrashing below him. He slows down finally, and I think I will be able to breathe for a second, but he just teases me. He brushes his thumb on my clit, very gently, and I think I’m going to explode.

I look at him and tell him, “I want to show you what it took all of my self-control not to do this morning.” His eyes go wide as I lick his cock from hilt to head just like a lollipop before curling my lips around him. His hands go to my hair and that drives me even more wild. I start moaning while he is hitting the back of my throat, loving the way he tastes in my mouth. I had to stop for a second to regain composure when I started to gag. As I try to catch my breath, I see a wicked smile run across his face. He asks, “Do you want to try anal?”

My eyes grow wide. I never in a million years thought I would hear him say that. This tall, nerdy, quiet man shocked me, in more ways than one. I’d never tried anal before, afraid of it hurting. For some reason though, I trust him. He asks if I want to control the pace, but I just tell him to go slow, and I’ll let him know if it hurts.

I bend over and I feel him at the opening of my pussy, rubbing his head there, spreading my cum around so he can use it to make entering easier. When he tries to enter me, I didn’t know if he would be able to get past the tight ring of my ass. Anticipation built within me, worrying about possible pain. When I felt the head of his cock enter me, it was the most pleasurably painful experience. He continues to go slow, pausing when the pain is too intense to let me acclimate to the feeling. Once he is all the way in, he starts gently thrusting, in and out, still letting me get used to the feeling of having pressure there. It’s all I can do to stay quiet; I have to bite the pillow to keep from waking up his housemate. He starts to pick up the pace, the electricity shooting through me building. I have to drop to my elbows because my arms start shaking too strongly from the overwhelming need to have a release. Just when I think I won’t be able to take it anymore, my orgasm tears through me, starting at my breasts, raging through my stomach, concluding in my womb. I feel my whole body go rigid with the orgasm and I’m not sure I’ll survive. I feel his body stiffen behind me at the same time, knowing he got his release as well.

I collapsed on the bed with him still in me. He follows suit and covers me with his body. I thought it was over, but when he slowly pulled out, my insides start quaking again. Everything sensitive and reacting to the slightest touch. I couldn’t have told you the day of the week or even what year it was.

I head to the bathroom to clean up and when I look in the mirror, I’m completely flushed, hair wild, and there’s a hickey on my neck. I get dressed to leave and that’s when I notice everything hurts. Not terribly but I definitely couldn’t wear any tight pants for a few days.

​

I’ve started a few more stories, so lmk if you liked this one.

Source: reddit.com/r/gonewildstories/comments/10w107u/mf_my_first_time_having_anal