Evan & Sadie [M26/F24] [anal sex] [male anal play] [blowjob] [pussy eating] [exploration and joyful discovery] [romance]

**Sadie**

 

Evan and I had been dating for about six weeks, but we were still figuring things out. We had been on a bunch of dates, from movies to dinners to romantic walks along Palisades Park, and they were all pretty much awesome. It was clear that we liked the same things, but there was a ways to go before we knew where our interests and behaviors diverged. What little things did I do that he’d discover that he hated? And what would I discover about him that I wouldn’t like?

But that’s what dating’s all about, right?

So I worried about the moment when Evan would say or do something that hurt or shocked me or drove me crazy, and I wondered if I would do the same thing. Nowhere was that more evident than with sex. It’s so personal that there’s always that fear that you’ll want the one thing that will turn off your partner. 

The good news was that Evan and I were totally hot for each other. We ripped each others’ clothes off the first time, and we had fucked enough to know that we loved each other’s bodies and that the passion we had for each other was real. But we were not yet at the point where we were comfortable enough to really share with each other exactly what we wanted or if we were truly right for each other. Now don’t get me wrong. That doesn’t mean that I felt like our sex life was vanilla. I just knew that we were both holding back. 

Why? Well for all those reasons I just mentioned. Maybe I needed a little more confidence, but I was worried that if I told Evan some of the things I wanted that he’d be repulsed or, worse, laugh.

Actually, that was our relationship in a nutshell: We really liked it, but we were holding back. The real question was when we would move to that next stage. Hell, I had never gotten to that next stage with ANY of my boyfriends. Maybe that’s when you know you are ready to get married—when you have the confidence and trust to share all your fears, needs, and desires.

It’s not that I didn’t trust him. We just didn’t seem to be at that “let’s talk about sex while we’re having sex” point. I was worried about him getting offended if I told him that he needed to push a little harder when he slid his fingers in and out of my pussy or that he needed to be a little lighter when sucking my clit. Would he think he was a lousy lover or less of a man?

For my part, I was still pretty much guessing what he liked. Did he mind that I didn’t spend a lot of time sucking his cock? Was he a blowjob-is-the-best-part-of-sex guy when I was a blowjob-is-an-appetizer girl? When he was fucking me, did he mind that I stroked my clit or was that a blow to his ego? Why didn’t he fuck my tits? Were they not big enough? Did he mind that I didn’t shave my pussy? I mean he didn’t say anything about those things.

So we both needed to share more. I just wasn’t sure I knew how. I thought I was falling in love with him, and because of that I was worried that I’d scare him off. I was frozen in this weird place where I absolutely loved fucking Evan, but I was worried that I’d do something wrong and he’d find some other woman who had bigger breasts or would suck his cock for twenty minutes while deep throating him or wouldn’t be so demanding about how he licked her pussy. 

Maybe small steps?

**Evan**

 

Sadie was, without a doubt, the hottest woman I had ever dated. Things were amazing. We loved doing so many things together, and she was awesome in bed. Holy shit, when I first saw her naked I thought I was going to come right there. She has this awesome round ass and the most amazing perky tits. 

Look at it this way: The first time we had sex, when she pulled her pants off and I slipped my hand down the front of her panties, she was so wet that my finger slid into her pussy before I even had a chance to lightly caress her clit or stroke her lips. How amazing is that? She was totally wet for me.

And just like our dates, she was fun and open in bed. I remembered telling her I wanted to fuck her doggy style, and she immediately rolled over, got on her knees, and looked back over her shoulder at me. She just stared at me with this sexy come hither look like she couldn’t want for me slide my cock into her. Jesus, I get hard just thinking about it.

So she’s hot and loved sex and was really great at just letting me know she wants me. Every guy loves that. But I have to tell you, one thing that I was hoping for but I was nervous about was being a bit more honest. I like to think I’m good at sex, but she didn’t say anything when I was going down on her. Did she like it when I fucked her with my finger while I was licking her clit? Did she want two fingers? When I sucked her nipples, did it turn her on or was it creepy when I really went at it? I kept thinking that it would be hot for her if I were to slightly pull her pubic hair as I licked her clit. Would she like that? I had no idea, so I didn’t. She didn’t spend a lot of time sucking my dick, but was that because she didn’t like it or she really wanted to feel it inside her pussy and couldn’t wait?

Of course, I couldn’t complain as I was nervous about telling her what I liked. I kept thinking that if I told her that she didn’t need to use her tongue so much when giving me a blow job that she’d just think, “Fine. If you don’t like my blowjobs, I’ll just stop giving them to you.” How could I tell her that I loved her riding me while I was on my back? Didn’t women like the take-charge type guys? How could I ask if I could slide my cock all over her tits and nipples? It’s not like she’d get any enjoyment out of my cock between her tits. I’d come across as as a selfish asshole. So I kept thinking that if I said anything she’d either be horrified or pissed off.

I didn’t know how to make progress. I was pretty sure that healthy couples actually talked about sex while they’re having sex, but how did you make that first move without jeopardizing everything?

**Sadie**

 

Evan was fucking me doggy style, and I almost asked him to fuck me in the ass. I didn’t because I thought he’d think it was gross, so I just lowered my head to the pillow and enjoyed the feeling of his cock going deep in and out of me. It was nice. It was better than nice. I fucking loved it. But I couldn’t stop thinking about what I REALLY wanted.

You see, I love anal sex. Maybe I’m weird, but a cock in my ass touches like every nerve ending. I cannot even begin to tell you how great the orgasms are when a guy licks my pussy until I come and then as I’m living off that high he turns me over and fucks me hard in the ass. It’s like every nerve that just got buzzed while I came gets turned up to 11. 

But here’s the thing—if you really loved a guy and you didn’t want to lose him and you had no idea how he felt about anal sex, there was absolutely no way to broach that subject without knowing that one of the scenarios was him being repulsed and you losing any opportunity of having those amazing orgasms again if you wanted to stay together.

I was so close to just blurting out, “Oh Evan, please fuck me in the ass right now,” but I just couldn’t do it. I mean, it was the perfect timing. He was behind me. I was on my knees with my ass right there. But I still couldn’t ask. What if he said, “Gross?” Or what if he destroyed the whole moment and said he’d do it if I got an enema first? I mean, come on.

Knowing that maybe a small move would lead to more I caressed his balls lightly with my fingers as I gave him a blowjob. I’ll admit it: I’m not a huge fan of blowjobs. I like giving my man pleasure, and feeling how hard he is as he moans while I’m doing it is great, but I prefer his cock in other places. 

So I decided to spend more time sucking him to see if I could try something new. As I caressed his balls, he seemed to like it, but it was maddening in that he didn’t say anything. I mean he moaned and was hard as a rock in my mouth, but he didn’t say anything like, “Oh my god, I love what you’re doing” or “Do more of that, please!”

Later he did do this amazing thing where instead of fucking me missionary style, he got on his knees and pulled my hips up. So he was fucking me from a kneeling position looking down on me while I was on my back. It seemed like kind of a porn move, but I went with it, and I was glad I did, as I soon found out what he was doing. As he fucked me he reached down and started to stroke my clit with his thumb.

Oh. My. God.

I had often stroked myself while he fucked me missionary style so we could come together, and that worked great, but this was so much better. His cock was sliding in and out of me while he was stroking my clit with his thumb, and there were moments when I could feel his thumb brush against my clit and his cock at the same time. 

I came so hard and fast. It was amazing. I may even have woken the neighbors. 

So while my ball stroking was probably a failure, I was psyched that Evan had learned from my masturbating while he fucked me to try a new position.

It was a start.

**Evan**

 

So she was sucking my cock, and it felt amazing. I could tell she wasn’t big on the blowjobs, which was perfectly fine. She had this amazing tight body, and I had plenty of other things that made fucking her an amazing experience. So she’s sucking me, and I was expecting her to stop when I got really hard and ready, but she did something else—she reached up and gently started stroking my balls with her fingers. I swear I was about to faint out of pleasure. I moaned really loud to give her an idea as to how much I loved it. I’m pretty sure that got the message across, because I wasn’t about to tell her I liked it. I mean, you can imagine if I had said, “I love how you are stroking my balls.” Just saying the word balls was probably a turn-off.  She’d turn away in horror and probably never do it again. 

Later I decided that I’d try something that was pretty much fool-proof. I had noticed that she stroked her clit a lot while I fucked her. A lot of women did that, so I knew she did it for additional stimulation. That’s not a problem, but I figured I’d try something to do that for her. I didn’t even tell her. I just got on my knees, lowered my ass to the bed, and pulled her hips up onto my thighs. It was awesome. I was holding her ass in one hand while I guided my cock into her pussy with another. 

So she was on her back, and I was fucking her from above, and I reached down and started stroking her clit with my thumb. She seemed to really like it, but I had no idea if it was better than she did herself. Was I too rough? Too light? What if I wasn’t as good as her? Actually, she knew exactly how to touch herself, so I was sure that it wasn’t as good as when she did it. 

The good news is that she came right around the same time I did, and it seemed like she really was into it. So maybe I was good enough. Still, I wish she had given me more guidance. Should I have stroked harder? Softer? Was I touching her in the right area? I just didn’t know. 

Still, while I was unsure if I had made good progress, Sadie had totally gotten me off while stroking my balls while sucking me. It wasn’t the Kama Sutra, of course, but it showed that she was willing to try some new things. 

Here’s the thing, though: The one thing I really wanted to do I was pretty sure she’d break up with me over just for asking: Fucking her in the ass. I had only had anal sex once, and it was both amazing and kind of awkward. When I started thrusting into her ass, the feeling was entirely new and wild and exciting. I loved it. But the woman wasn’t into it at all, and she seemed only to be excited that I was excited. While that’s nice, it’s not the same thing as both of us being into something. 

She asked me not to come inside her. So I came on her ass, and she seemed kind of annoyed at the whole mess. I mean, isn’t the crazy mess the price you pay for amazing sex?

We never had anal sex again. I was going to wait for her to ask for it, but she never did, and that’s how I knew it wasn’t something she was into. But here’s the thing: I missed it. It’s not that it’s better than a pussy. It was just different. 

So I really wanted to ask Sadie if we could try anal sex, but how do you ask that? I was afraid she’d say it was disgusting or that I was a pervert. And I was torn between two fears: The fear that she’d break up with me, and I’d lose her, and the fear that she’d not break up with me, and I’d never have anal sex. I know; I’m shallow. But there it is.

 

**Sadie**

 

I hadn’t seen Evan for four days as he was out of town for a work conference, and I was incredibly horny. I needed him. I needed his cock. I just badly wanted to fuck. It was such a level of horniness that I was desperately thinking of ways to get him to lick me until I came and then have him roll me over to fuck me in the ass. 

Just thinking of that was getting me so wet that I had to change my panties. 

He was coming home at midday, and we were to have dinner at our favorite restaurant as a welcome home date. But what I was really thinking of was a good hard fuck. 

So I put on a tight dress without any underwear and met him at the restaurant. Dinner was the last thing on my mind.

 

**Evan**

 

I hadn’t seen Sadie in four days, and all I could think about was her hot, wet pussy. Just thinking about her got me hard at the airport. I had to make my way off the plane and into the cab while hiding a hard-on. I mean every guy goes through that, but come on. I’m not sixteen any more.

I was so horny that I wanted to do something wild and new—something really hot and special. I thought of tying her up with my tie or showing her how wild I was for her by pushing her against the wall and fucking her standing up right then and there. 

I wasn’t quite sure what I was going to do. All I knew was that Sadie was the hottest woman I had ever met, and I needed my cock inside her.

**Sadie**

 

I was wet the moment I saw Evan. He walked into the restaurant, saw me, and waved, but what I really saw was this animalistic desire in his eyes. He looked at my black dress, and I knew that all he wanted to do was rip it off. 

Oh, yes.

But I had no idea how badly he wanted me until he sat down in the chair next to me at the table and immediately slid his hand up my dress. Normally Evan will sit across from me and we’ll stare into each others’ eyes and talk and laugh while looking at each other. We were sitting at a table for four, and Evan sat in the chair right next to me. 

He leaned toward me.

 

 “Spread your legs.” 

 

I felt his palm slide up my thigh.

I opened my legs 

 

“Someone missed me.” 

 

I smiled just as his fingers brushed against my pussy lips. I gasped and looked over at Evan.

He had the hugest smile on his face. 

 

“It feels a lot like someone was missing ME!”

 

I was going to laugh, but at that moment his finger tips started toying with me, lightly stroking my pussy lips. I gasped, and slid my hips forward trying to will him into sliding his fingers into my pussy. He didn’t, and I was dying. I had to get back at him somehow, so I reached over and slid my hand between his legs.

 

“I did miss you,” 

 

I squeezed the bulge in his pants, and holy shit did I. It felt like he had an iron bar between his legs. 

 

“Someone else is also happy to see me,” 

 

Rather than reply, Evan finally slid a finger into my pussy, slowly sliding it in and out while staring at me. I think I may have actually moaned as it felt so good. I was tempted to close my legs, forcing his hand to remain, but I was good and just watched as he pulled his hand to his lips and sucked on the tips of his fingers.

 

“Nothing tastes better than that,”

 

I was so tempted to ask him if we could just up and leave so we could head to my place, but Evan seemed in no hurry, so I worked my way through dinner, although all I really wanted was to feel his cock inside me.

**Evan**

 

I was so close to just taking Sadie by the hand and dragging her out of the restaurant to fuck her against the car or in the alley or right on the lawn. God, she was so fucking hot. She looked at me with those “fuck me” eyes, as if daring me to do what I wanted.

But at that point the waiter arrived, and it would have been awkward to just say, “We changed our mind. We are leaving.” So I ordered for us, and we had a wonderful dinner full of laughs, interesting stories, and plenty of double entrendres.

In the end I was glad we had dinner as it did calm my desire down a bit, which was great because I was looking forward to amazing sex with Sadie, not just a hard fuck against the car. Not that a hard fuck against a car was bad, but I wanted something more. Sadie apparently did, too, for as we walked to the parking lot, she pulled me close.

 

 “You didn’t say anything about me not wearing underwear.” 

 

Her voice was breathy and kind of tentative. 

 

“Are you kidding? You felt how hard my dick was. When I felt how wet you were and that you didn’t have panties on, I wanted to fuck you on the table.” 

 

That was about as provocative as I had ever spoken to her, but if she was going to risk honesty with me I owed her the same. As I glanced at her I could tell she loved it. 

 

“I would not have minded at all if you fucked me on that table.”

 

“The other customers may have minded.” 

 

We both smiled, and I squeezed her hand. I loved how our conversation was going. While we were pretty sexual, this was the first time that we were this free and easy with our conversation.

As we buckled in, I ran my hand up Sadie’s leg again. 

 

“Why don’t you tug your dress up a bit?”

 

She looked over at me. 

 

“Why don’t you unzip your pants and pull them down?” 

 

She had a smirk on her face that told me she didn’t think I would do it. So as she started to pull out of the parking space, I lifted myself a bit off the seat, undid my belt, unzipped my pants and tugged them down to my knees. My dick was rock hard, and I reached down and wrapped my fingers around it and stroked it a bit.

She glanced down. 

 

“Oh my god, that is so hot.” 

 

I ran my hand up and down my dick, and her eyes went wide. 

 

“Fuck. Don’t stop. Keep doing that.” 

 

Sadie had never asked me to masturbate for her, and it was a total turn on. I didn’t want to come, but I knew that just giving myself some slow strokes wouldn’t get me off, so I did. 

I thought Sadie was about to drive off the road.

**Sadie**

 

I nearly drove off the road. 

Evan’s cock was hard as a rock, and he was sitting there in the light of the setting sun stroking it. I stopped at a stoplight and looked over. Evan was smiling as he continued to slowly stroke himself.

 

“You didn’t tell me to stop,” 

 

he had a smile on his face.

 

“Oh, you most definitely should not stop.” 

 

I looked down and saw a glimmer of precum at the tip of his cock. Then Evan slid his thumb over the top of his cock and rubbed it around the head, spreading the precum. I couldn’t help myself and slid my hand between my legs. I was so jazzed I was ready to come myself.

 

“As much as I would love to watch you sit there and get yourself off, you have to drive us home,” 

 

Evan nodded toward the front of the car. I noticed the light had turned green and went back to driving as he tugged up his pants. 

I glanced over and looked him in the face. 

 

“You’d like to watch me masturbate?” 

 

I had just admitted I liked it with him, and he was kind of saying the same thing, so I felt comfortable asking. But it sounded kind of weird asking him if he’d like watching me masturbate. I didn’t know why. 

 

“You masturbating in front of me? Are you kidding? Do you realize how hot it is to watch a woman do that? Please please please touch yourself whenever you want. If I walk in and you’re masturbating, I’ll just happily watch.”

 

“Or you could join in,” 

 

“Even better,” 

 

I was in a bit of shock. Our desires were leading us to talk about things in more openness than we ever had before. I loved it. This was what I had hoped for from the start. Did we perhaps turn a corner? It was then that I knew I wanted to just totally let loose when were in bed. I had no idea if I had the guts to do it, but after dinner, the car ride, and then Evan telling me how hot it would be for him to watch me masturbate? There no longer seemed to be any danger in us being too naughty for each other.

**Evan**

 

Jacking off for Sadie was incredibly hot, but it wasn’t remotely as hot as her sounding excited about the concept of masturbating while I was around. What guy doesn’t want to walk into a bedroom and see a woman stroking herself? That’s like male fantasy 101. 

And Sadie totally got it. 

We stumbled into her apartment with our hands all over each other. 

“God, I’ve missed you,” 

I kissed her neck and then moved up to her lips. We had stopped in the entryway for a long, hot kiss. Our bodies were pressed against each other, and I knew she could feel how hard I was through my pants. I ran my hands over her back and then slid them down to her ass. 

She pulled away from our kiss and then moved forward and lightly licked my nose. I met her tongue with mine and pulled us close so I could tug up her dress with my hands and caress her ass. As I did that our tongues danced between our lips. 

Giving me a slight push, she reached down and stroked my cock through my pants. I was so fucking hard. I pushed her back, and gently pressed her against the wall. She looked up into my eyes as I reached down and grabbed the bottom of her black dress. I lifted the whole thing up and over her head, and I about lost it as she lifted her hands above her head and her tits gave a little shake as she flung the dress aside.

I think she thought I was going to fuck her right there against the wall, as her hand reached for my belt buckle, but I had other ideas. I kissed her lips and then her chin and then her neck as my fingers ran over her nipples. I kissed her again as I gave them a gentle squeeze, she tensed. 

“Do you like that,” 

“Oh yes,” 

“How about this?” 

I leaned over and wrapped my lips around one of her nipples. I licked and sucked while my hand caressed and squeezed her other nipple. At one point, I sucked her nipple in and out of between my lips, and she tensed again. Was it weird? Is it possible to suck a nipple too much? I thought it might be creepy, but then she moaned.

 

**Sadie**

“Don’t stop. That feels soooo good.” 

It was amazing. Evan was spending all this attention on my breasts, and it felt incredible. Guys usually ignored my breasts unless they wanted to slide their cock between them. I didn’t mind that, but I had always assumed that I’d not get much more.

But this was more. So much more. 

Evan ran his tongue from my one nipple, across my cleavage to my other nipple, and then did the same thing all over again. After spending a delicious amount of time doing that nipple-sucking thing he did that felt so amazing, he pulled back  

“I really like this.”

“I’m glad, because I want you to do that to me again. Like, all the time.” 

And then a crazy thing happened. Evan laughed. And then I laughed. It wasn’t awkward. It wasn’t horrifying. It was wonderful. We were both enjoying something and the words we spoke just made it, I don’t know, fun.

Before I could even think of returning some kind of favor to him by sucking his cock or giving him a hand job while we kissed, I felt him run a trail of kisses down the front of my body until he reached between my legs, where he kissed each of my thighs and then ran his lips all over my pubic hair. No guy had ever done that, and it was amazing, like he enjoyed the feel of my hair against his lips. 

We had kind of committed to talking, so against my instincts I spoke up. 

“That feels good.”

“What? This?” 

And at that moment I looked down, and the vision was so hot—Evan on his knees, his lips pressed brushing against my pubic hair as he was looking up at me. I nodded

“I love how soft it feels.” 

Did he just say that? I didn’t know what to say, but it didn’t matter because just then he spread my pussy with his thumbs and kissed my clit.

“Oh god. That feels so good.” 

“You are so wet,” 

And then he lifted my leg and set it on his shoulder, spreading my legs. No man had ever gone down on me while I was standing, and Evan made it feel so natural and so hot. 

He ran his tongue up and down my pussy, and I just tossed my head back and leaned against the wall. He started to suck on my clit, and I put my hand on his head. He looked up, 

“That’s just a little too hard. I do like that, but be gentle.”

He didn’t say anything but instead I felt his lips softly brush against my clit and then he gave a gentle suck. 

“Oh yes. Fuck, that feels good.”

He continued giving long licks and gentle sucks. 

“Oh god, I’m going to come if you keep that up.” 

It wasn’t just that he followed my direction, but holy shit was he good at following directions, it was that he added little surprises that just raised the temperature even higher. 

It wasn’t just long lick. Light suck. Long lick. Light suck. He’d change things up just enough that ohmygoditdrovemecrazy. Long lick. Long lick. Light suck. A light flutter of his tongue on my clit and then he’d run it slowly up and down the inside of my lips. 

It was when he slid a finger into me that I knew I was going to come hard against the wall with him between my legs. His technique was good, as he was moving his finger up along my the top of my pussy to my G spot, sliding it in and out. The thing was he was being way too gentle, 

“Slide another finger in” 

He did and his two fingers stretched and filled me. It still wasn’t enough, 

 “faster.” 

He slid them in and out faster. By then I was getting closer, but I wanted it hard. I NEEDED it hard. So I just fucking went for it. 

“Harder.”

And holy fuck that did it. He slammed his fingers in and out. It was so fucking hot, but then he leaned forward and started licking my clit while he finger fucked me. 

“Oh god, yes. Fuck me hard and fast with your fingers. Slam then into me. Pound my pussy.” 

I couldn’t believe I said those words, but all I know is that Evan fucked my hard with his fingers while he licked my clit, and I think I may have screamed from the orgasm. 

 

**Evan**

The intensity in her voice was amazing. She practically screamed the words “pound my pussy.” I had fucked quite a few women and gone down on every one of them, but this was about the hottest experience of my life. Sadie was practically dripping she was so wet. Her pussy was swollen like it was inviting my tongue to taste every last inch, and she tasted so amazing.

But you know what was hotter? How she finally gave me some direction. Each time I followed what she said, it was as if she got that much closer to orgasm. When she asked me to go faster with my fingers, I wasn’t sure how much faster or harder she meant, so I went a little faster and pushed with just a little more force, but then she said, “pound my pussy” With this kind of desperate urgency.

So flicked my tongue against her clit and rammed my fingers in and out of her pussy. I was actually worried that I was going to hurt her, but the leg on my shoulder started to shake, and she cried out for me not to stop.

She started to moan and literally grabbed my hair with both hands and pulled me in so she could grind her pussy against my face. It was unbelievably hot, and I loved how she just used my mouth for her pleasure.  I felt her thighs and and pussy clench. 

She was breathing heavily as she gave my head a gentle push away and she slid her leg off my shoulder. I stood up, and she grabbed me. Her legs were weak, and I loved that because she clearly had an amazing orgasm. 

I was wondering if she needed time to recover, but as I stood in front of her she had her hands caressing my cock through my pants. I had assumed that she’d need a break, and I’d just finish by masturbating or something, but the intensity in her eyes as she stroked me through my pants was intoxicating. 

“Oh, it is SO your turn.” 

She grabbed my hand and pulled me toward the bedroom. 

At the base of the bed, she spun me around and gave me a hard push. I fell back and landed on my back, bouncing slightly off the mattress. She was on top of me shortly after. We kissed, and she unbuttoned my shirt, kissing my body as she revealed the skin underneath.

Before too long she had ripped off all my clothes. My feet were on the floor, and I was on my back, and she was between my legs. She kissed the tip of my dick, and as I looked down she was looking at me. As our eyes locked, the moment was incredibly hot. My cock was in her hand, and she had the look like there was nothing she wanted more in the world than my cock.

“Your turn,” 

Then she slid her lips around my head and pushed her mouth down, sliding my cock into her mouth. I knew I was in for something amazing when she ran her lips along the side of my shaft as her thumb caressed the head of my cock. 

“Wow, where’d you learn that,” 

“From watching you in the car earlier tonight,” 

“This, however, is something I learned from porn.” 

She then licked my my cock from the head to the bottom. But then she didn’t stop and started to lick my balls. She ran her tongue all over them and then gave a slight suck on one. 

“I’m definitely a fan of you watching porn.” 

She  looked up at me and smiled. God, she couldn’t be any hotter.

But then she was.

 

**Sadie**

“THAT’S not what I learned from porn,” 

His eyes went wide in this amazing look of animal desire and anticipation. 

At that point I felt strongly that we were in tune with each other. I could ask or do anything, and he would be respectful and honest. He may not like it, but he’d tell me and gently give me guidance on what to do. It was freeing and felt amazing. It was almost like sex had entered an entire new level for us.

I was still jazzed from my orgasm, which was one of the strongest I could remember. The way he went from soft thrusts with one finger to pounding my entire pussy with his fingers tight inside me took me to a new height. But then, his passion, his excitement, his total enthusiasm for how I fucked his face until I came. THAT’S trust and connection. 

So with all kind of heat and confidence behind me, I decided to do something crazy. Because I knew I was going to ask Evan for anal sex. I figured I’d illustrate how great it felt. When I told him I learned something from porn, I didn’t lie, but I said it to prepare him for something wild in the hope that he’d be ready to do the same thing.

When I was just starting to have sex I would watch porn to figure out how to please a man. That was pretty good, but I REALLY wanted to get my partner off. And one of the things I learned browsing Discord was that a guy can have multiple orgasms via anal sex.

Well, not anal sex, prostate stimulation, but that didn’t sound sexy at all, and I loved anal sex, so I just considered it that. The thing was that I never had a boyfriend where I thought I could even bring it up, even though it was supposed to be great for the guy. 

But now I had that guy. I KNEW I had that guy.

So I stroked his cock with one hand, licked his balls, and then caressed his asshole with a finger from my other hand. I knew the process but wasn’t sure I could do it right. Stick your finger in, stroke inside pretty hard. But first I had to see if Evan was into it.

As I run my finger tip around his tight little hole, he gasped. 

“Whoa, that feels amazing.” 

I was so happy I could have cried. He didn’t mind me playing with his asshole. 

I dripped some saliva on my finger and at the same time I started to caress the head of his cock with my hand and fingers and giving it the occasional like and suck while I shoved my finger into his ass.

I was really nervous, so I pulled back.

“Are you okay with this?”

“It’s weird, but I kind of like it.” 

I pushed my finger in further and then used the “come hither” motion that I learned, stroking the base of his cock from inside his ass.

“Oooh. That feels good. REALLY good.”

“If I do it right, you’re supposed to be able to have multiple orgasms.” 

I loved how we were fucking and talking, and the conversation was all about pleasure for both of us. It was like the conversation was part of the sex. I couldn’t believe how hot it was.

“You know. I REALLY like orgasms.” 

I once again took his cock in my mouth. He moaned a bit as I stroked my finger inside his ass. It felt really taboo and really hot, like I was doing this really naughty thing, and Evan was digging this naughty thing I was doing. I pulled my mouth away and decided to just stroke him with my hand and enjoy looking at his gorgeous cock as I fucked his ass with my finger. 

I wondered if this is what it felt like for a guy to have anal sex with a woman—kind of taboo and hot in the giving-pleasure-to-your-partner kind of way. 

“Okay, this feels really good, but I don’t think I’m going to come.” 

I was stroking his cock with my hand and watching his face as I slid my finger in and out and stroked with my finger. 

“Maybe I’m doing it wrong?” 

I asked as I slid my finger out. He pushed himself up and leaned forward, kissing me on the top of my head. 

“You’re not doing it wrong. I just think it’s just something that we’ll have to practice. Maybe you have to do it harder?”

After giving the head of his cock a kiss, I stood up. 

“Oh, I’m totally into practicing that.” 

We smiled at each other. I couldn’t believe it. 

“I’m going to wash my hand. Maybe you can lie back and stroke yourself for when I come back?”

I walked back in later, and that’s exactly what he was doing.