Anal Sex

[Cherylxd]

Crossdresser here, story first before the real question since many will pm for story. 

 

2 night back when I was dressed, short flared mini dress that barely cover my panties, thigh high and high heel. A cute guy approached me, he introduced himself and asked to make friend. We went to the block table, sat down, smoke some cigarette and chat.

 

He's not bad looking, maybe around 30s? While we chatting, he inched closer and closer to me and before long, he was beside me. My heart was pounding at this moment and I can feel his breath down my neck. I can feel my dick pulsating thru my panties. He asked if I was nervous (who wouldnt?). I asked him what he wanted and he smiled. He put his hand over my chest, reach for my back and pull me close to him, before long, we will hugging, he tried to kiss me on the lip but I turn away. He then started necking me. I let out a small moan, I didn't meant to but it feel really really nice. He took my hand and put it onto his pants. I can feel his very very hard dick, I traced the outline, it wasnt big, just very very hard.

 

I asked if we could go to somewhere more private, he led me to the lift and we went to the staircase landing between the 8 and 10 floor, it was quite secluded as it is a mansionette block.

 

He had me in a embrace n started necking me again, slowly he move his hand from my back and to my butt, fondling them as I moan with pleasure. I had my hand feeling his cock thru his pants. He rubbed me thru my skirt and before long, he tried to reach into my panties, I pushes his hand away as I feel embarrassed to be touch this way by stranger.

 

My hand on his chest, I kneeled down slowly and was soon eyes level with his crotch. I kissed his dick thru his pants while undoing his belt and pants. His strong dick sprang out as soon as I pull down his pants and underwear.

 

I took out the condom in my purse, I alway have condom and lube prepared and I wont do raw bj and the lube was in case, I were to be raped.

 

I slip the condom on for him and took his cock into my mouth. It is abt 4 inch long and not thick at all. My panty wet with my precum.

 

I was feeling really horny, I have suck a few dicks but never get farked before. I haven't cum for weeks and I really want to release. I didn't want himto cum and I'm have to wait till I get home to masturbate, I just could hold it any longer. I told him to fark me. He look a bit shock but he grab me and bend me over the parapet.

 

With his legs, he push my leg apart, he hitch my dress up and pull down my panty, took the lube and wet my hole.

 

He fingered my ass and I moan with great intensity, I have never had anything up my ass before, it just feel different and I feel my leg shiver and grow soft with every thrust with his finger, he was really sticking it in and I could feel his finger up my balls, there is this feeling that I cannot describe.

 

I can feel his dick head against my hole, I took his dick in my hand and position it onto my hole.

 

I can feel the pressure from the dick head up my but no matter how he tried, he could not get his dick in. It was quite disappointing for us as we are really horny. Its started to hurt now. He managed to get a bit of his dick head in but I pushed him off as I feel my ass tearing up.

 

In the end, I just jerk him off.

 

I bought a butt plug ytd and I tried to push it in but I cannot. I can insert my finger thou.

 

The question is, how do I let a guy fark me in the ass? I mean is a small dick and butt plug, why is it so difficult.

 

 

 

 

 

 

 

 

[Guest Tomm78]

Pm me or add me on telegram,  my ID is T0mm81 

[snowbored69]

It really comes down to relaxing and learning how to control the muscles down there. Especially in a hot and heavy situation like that you probably tensed up and that would be painful for anyone. I recommend playing more by yourself and get a toy that's about the right size and just practice letting it in and out of you. When you're bored and just sitting around, try contracting and losening the muscles too. You'll get there, promise!

[Cherylxd]

I lube aplenty today..managed to get one butt plug in..is small size then I tried a bigger butt plug..feeling adventurest, I lube more, used up maybe half a tube of lube and inserted a dong up. Oh my god!!

 

First an inch then 2, before long, I taken the whole 4 inch. Thrusting harder and faster.  I moan non stop. Now I know moan are voluntary.

 

A strange feeling came but there is no cum!! Is feel better then coming normally.

[tiemeup]

I have the same challenge. Always fantasised about getting a prostrate orgasm or getting fucked in the ass but I'm just too tight that it hurts. A guy tried to penetrate me once but it just couldn't go in so I sucked him off.

 

That said, I do love having toys in my ass. Have tried to open my ass with toys before while self-exploring. There's a different feeling of wanting to cum, but when I thought it was an orgasm and decided to just relax and let the sensation overcome me, I ended up peeing instead. At least I think it was pee based on the smell and it was just liquid, not the consistency of cum. So now I'm a bit self-conscious about ass play. Scared I can't differentiate the feeling of an orgasm or peeing as well as how tight I am.

[Saggiboy]

It's a matter of learning to control your muscle, and really open up your hole all the way in. The way tops tease and fuck also help to make your hole so horny that it opens. Up to wanna swallow the whole cock. When I m totally opened, and the top start fucking hard and fast, the ultimate orgasm for both and explore at same time. 

[Copper2b]

That’s fucking fun

[sgtwinkbottom_]

On 10/31/2022 at 11:06 AM, Cherylxd said:

Crossdresser here, story first before the real question since many will pm for story. 

 

2 night back when I was dressed, short flared mini dress that barely cover my panties, thigh high and high heel. A cute guy approached me, he introduced himself and asked to make friend. We went to the block table, sat down, smoke some cigarette and chat.

 

He's not bad looking, maybe around 30s? While we chatting, he inched closer and closer to me and before long, he was beside me. My heart was pounding at this moment and I can feel his breath down my neck. I can feel my dick pulsating thru my panties. He asked if I was nervous (who wouldnt?). I asked him what he wanted and he smiled. He put his hand over my chest, reach for my back and pull me close to him, before long, we will hugging, he tried to kiss me on the lip but I turn away. He then started necking me. I let out a small moan, I didn't meant to but it feel really really nice. He took my hand and put it onto his pants. I can feel his very very hard dick, I traced the outline, it wasnt big, just very very hard.

 

I asked if we could go to somewhere more private, he led me to the lift and we went to the staircase landing between the 8 and 10 floor, it was quite secluded as it is a mansionette block.

 

He had me in a embrace n started necking me again, slowly he move his hand from my back and to my butt, fondling them as I moan with pleasure. I had my hand feeling his cock thru his pants. He rubbed me thru my skirt and before long, he tried to reach into my panties, I pushes his hand away as I feel embarrassed to be touch this way by stranger.

 

My hand on his chest, I kneeled down slowly and was soon eyes level with his crotch. I kissed his dick thru his pants while undoing his belt and pants. His strong dick sprang out as soon as I pull down his pants and underwear.

 

I took out the condom in my purse, I alway have condom and lube prepared and I wont do raw bj and the lube was in case, I were to be raped.

 

I slip the condom on for him and took his cock into my mouth. It is abt 4 inch long and not thick at all. My panty wet with my precum.

 

I was feeling really horny, I have suck a few dicks but never get farked before. I haven't cum for weeks and I really want to release. I didn't want himto cum and I'm have to wait till I get home to masturbate, I just could hold it any longer. I told him to fark me. He look a bit shock but he grab me and bend me over the parapet.

 

With his legs, he push my leg apart, he hitch my dress up and pull down my panty, took the lube and wet my hole.

 

He fingered my ass and I moan with great intensity, I have never had anything up my ass before, it just feel different and I feel my leg shiver and grow soft with every thrust with his finger, he was really sticking it in and I could feel his finger up my balls, there is this feeling that I cannot describe.

 

I can feel his dick head against my hole, I took his dick in my hand and position it onto my hole.

 

I can feel the pressure from the dick head up my but no matter how he tried, he could not get his dick in. It was quite disappointing for us as we are really horny. Its started to hurt now. He managed to get a bit of his dick head in but I pushed him off as I feel my ass tearing up.

 

In the end, I just jerk him off.

 

I bought a butt plug ytd and I tried to push it in but I cannot. I can insert my finger thou.

 

The question is, how do I let a guy fark me in the ass? I mean is a small dick and butt plug, why is it so difficult.

 

 

 

 

 

 

 

 

Calm down. Deep breaths and take it in. Use alot of lube if needed.

 

I admit it's gonna be painful but after a while the pain turns into pleasure. 😈😈😈