My Butch Lesbian friend took my anal virginity.

Kris and I have known each other for years. I can say we are great friends. We have both been know to be the wing man for each other over the years. She is full on Lesbian. May be the most Tomboy Lesbian I know but she loves being a woman. Although she has short hair, dresses like a man, acts like a man, and is very Dominant in her every day life. She does not call herself trans, or feel she is a man in any way. Again, she loves being a woman.

Kris and I are out in a bar hanging out drinking. We were both being the wing man today. Kris and I have both ben single for some time and we both were in need.

It was a slow night at the bar but we were still having a good time hanging out and having drinks. Talking about anything and everything.

First, I want to say. I have never found Kris hot. She is a great girl and her personality does have a cham to her. But I can say I have never thought of her as sexy and that I would want to take her home. But at the same time there is a part of me that finds her to has a sex appeal that is intriguing. But never really gave it much thought.

Well, at some point in our drunken mess. Sex came to the talking point. We were talking about ex’s and so on. I asked her what was in it for her to using a strap on and she told me. My strap on is a strapless one. It goes in my pussy so when I’m fucking it feels good for me too. then anal came up.

She asked me If I liked anal. And I said, yes love it.

I asked her if she preferred anal or pussy.

She tells me, she loves pussy but there is something so taboo about anal that makes me want that more.

We talked about anal for some time and then I asked her why she has never been with a guy?

She tells me, I have never really been attracted to men. Girls just do it for me you know. But as I get older. There is a part of me that would not mind trying to fuck a guy.

She asked me the same thing. Why I have never been with a guy? And for the most part the same answer. I don’t find guys hot. So, I have never put much thought into it. I will say this. I’m not looking for it but at the same time. Right place and right time. May be fun to explore.

Our talk is now bouncing around anal, and guys. Both for her and me.

She then said, damn I’m horny as hell now. All of this talk makes me want to fuck a man.

She looks right at me and asked. Do you want to fuck?

I’m thinking to myself. Again, she is not hot. But this talk has me going also. And it would be hot to be her first guy.

I looked at her and said, would love to be your first guy.

So, we leave and get to her place. We start to kiss and it is odd. You can tell by our kiss we are not a good fit but we both keep going. Both of our hands are roaming around each other. I’m pinching her nipples and she is now moaning in my mouth as we kiss. She is gripping and feeling my ass. I thought it was odd as you would think she was with a guy for the first time, she would want to feel my cock. But she keeps rubbing and gripping my ass. I thought she must like the feel of my cock grinding to her pussy. So I keep my cock to her pussy as we start to take each other’s shirts off. She undid her bra and it dropped and she went right for my nipples and started kissing and sucking them. Again, hands on my ass gripping me.

I pull her to me in a kiss again. I start to kiss down her neck and my hand goes to her jeans and I undo them. I wrap my lips around her nipple and one of her hands is on the back of my head holding me to her nipple as I suck and kiss it. I get her pants open and slide my hand in and she is so wet.

Her hand goes to my pants now and opens them up. She lets her hand rub my cock once and then both hands go in my pants and she cups my ass pulling me to her tight. I slip my wet fingers out of her and move my hands to her ass so my cock can grind to her pussy again for her. I want her to want me in her.

She stops the kiss and she tells me. Let’s got to my room. I fallow her in and she starts undressing all the way. I just watch her. She is now naked looking at me waiting for me. I take the rest of my cloths off. I fold them and I turn my back to her. To lay my clothes down. I turn back around and she is in a drawer next to her bed and she pulls out lube. That is when it hits me my condom is in my pants. So, I turn my back to her I pick up my jeans and sift through the pockets.

She comes up to me and I feel a hand on my ass. She moans a little and then tells me I have a really cute ass. I now feel her hands grip my hips and a kiss to my neck.

I find the condoms and pull them out. She laughs seeing them and said, you will not be needing those.

Just then she pulls me to her and I feel her cock on my ass. I freeze as I do not know what to say.

I turn around to see her strapless dildo in her and sticking straight out to me. Then I look at her and start to laugh. Here we are both hard and ready to fuck. But we may have not been o the same page.

I tell her. I think we miss understood each other. When you said you wanted to know what it would be like to fuck a guy. I was thinking you wanted to feel a real cock for the first time.

She starts to laugh. I thought when we are talking anal. You said you loved it. That is way I asked why you have never been with a man.

Oh, you thought I loved anal to me. More laughing. No, I’m 100% anal virgin here.

We are both laughing and shaking our heads. But at the same time. I’m still very turned on and standing there hard. She is standing there with her cock in her pussy and I can tell as she is turned on still also by the way she is swaying her hips it feels good to her.

I ask now what?

She thinks for a minute. Then comes out and tells me. Ok I will let you fuck me for my first man if you let me take your anal virginity.

She steps to me and her hand for the first time wraps around my cock and slowly stroke it. I’m drunk and so worked up that I give in to her and say deal.

She walks around me and comes up to my back and is kissing my neck again. I feel her pull me to her and her cock slides and rest between my cheeks as she holds me and kisses me. As She is playing with my nipples my hips, I feel her rocking her hips and moaning to me. Then she plays with my ass and ever now and them a soft stroke to my cock. It is like she knows what she is doing. As long as she has me this turned on. She gets to fuck me.

She walks us to the bed and lays me face down. She is kissing all over my back and then she does something I never thought would happen to me. She starts kissing and licking my ass. It feels so good I just give in to her. I swear I felt my cheeks opening up for her.

I feel her pulling my cheeps open and I feel her tongue touch my star for the first time. I moaned. She kept doing this for some time and ever now and then she would push the tip of her tongue in me and fuck it felt so good. I can not help but to moan for her.

With my ass being all nice and wet. I feel her slip a finger in me and my body shook. It was the first time anything ever made it in me. I grip the sheets and bit my lip. As her finger is in me and grabs the lube. I feel the cold from it and her finger is now sliding in and out of me.

I whimper out and I feel me get tight again and I know she has added a finger to my ass. It does not take long and I’m enjoying what she is doing to me. As she is finger fucking me. She is kissing all over my back and telling me how good I’m doing. She can feel me rocking with her fingers now and knows I’m ready.

I’m lost in all of this now. I’m moaning, breathing hard, and now rocking with her fingers going in and out of me. I’m loving it.

She slides her fingers from me and I whimper out as I didn’t want her to stop. She rolls me over and slides between my legs. We are in a full-on kiss now I slide my hand down her body to play with her pussy but I find her cock. She tells me to stroke her that is feels good inside her. I’m gripping her cock and stroking it. As I do sure enough, she is moaning for me. I feel her hips rocking with me as if she is fucking me. Then I feel the head of her cock rubbing my star. I can’t help it. I want her now. I moan in our kiss. Fuck me.

She pulls from the kiss She grabs the lube and strokes her cock with it. Then she lifts my legs up and slide her lubed finger back in me. My body shakes and I moan. She fingers me for a little bit and then pulls out. The head of her cock is now at my ass and I feel the pressure. I know it is going to hurt at first but I want it now. I help her with a little rocking forward to her as she is pushing in me. The head pops in me and I whimper. She holds still as she is in me. My eyes are closed waiting for me to relax.

I feel her wrap her hand around my cock and stroke and that is what I needed. She is slowly sliding deeper in me. The more she moves the more she moans with me. I feel her hip hit me and I’m so full. She slides out and then back in. She moans out oh fuck. It does not take too long and I’m moaning for more and she is fucking me.

She takes her hand off my cock and is now fucking me and I’m moaning for her to keep going. Her moans are only turning me on mow as her toys is making her feel good also. She is pulling back and drive a little harder in me. We are both moaning together. There is something about the feel of her hips driving in me and the feel of her cock. She must be hitting my prostate. I’m so close to cumming. I tell her. I’m going to cum. She moans out me too. And keeps fucking me.

I look down and ever though this feel amazing. My cock is not fully hard any more but still stiff. There is a big mess of precum all over me. I can not help it but I’m going to cum and I have no control.

She starts to shake also as she is driving in and out of me. She moaning out “ fuck” I’m going to cum.

I’m just a whimpering mess of moaning. And begging to cum. She drives a couple of more times and my cock lets lose. I shoot cum all over myself and that sets her off and she cumms, dropping to me and shaking as we hold each other.

Source: reddit.com/r/Erotica/comments/m8kz36/my_butch_lesbian_friend_took_my_anal_virginity