Reset Password
If you've forgotten your password, you can enter your email address below. An email will then be sent with a link to set up a new password.
Cancel
Reset Link Sent
If the email is registered with our site, you will receive an email with instructions to reset your password. Password reset link sent to:
Check your email and enter the confirmation code:
Don't see the email?
  • Resend Confirmation Link
  • Start Over
Close
If you have any questions, please contact Customer Service
Hookup, Find Sex or Meet Someone Hot Now

Just the Tip - I Tried Anal for the First Time  

oksylvia1992 32F
217 posts
4/7/2016 1:06 pm
Just the Tip - I Tried Anal for the First Time


[ this really happened ]

I've been dating a couple for a while. We've gotten together every week since we first met and sometimes more often. I'm very comfortable with them and they are very open about what they like and don't like. When we first played together we had the talk about limits. I told them I was so new and sexually inexperienced I didn't know my limits except I won't do deep throating.

The most recent time we were together she and I were playing while he mostly watched and ran his hands around our bodies. She got me to roll onto my stomach and started licking around my ass hole. She's done it before and enjoys how much it turns me on.

She slid her hand under me and rubbed my clit. I felt the tip of her tongue poking into my ass hole and it felt so good I pushed my ass back trying to get her to go deeper. Raising her head she kissed my ass cheek and moved her finger from my clit to my ass hole.

Circling her finger around my ass hole she asked, "Feel good?"

"Yes." I was so turned on and wet I could feel my juices oozing out and dripping down towards my clit. I squirmed around and thrust my ass hole against her finger. She slowly slid the tip of her finger inside.

I stopped moving and moaned. She kept the tip of her finger in my ass for a few seconds then slowly pulled it out and pushed it slowly back in. This time she pushed her finger a little deeper as I thrust my ass toward her hand.

We developed a slow rhythm. Each time I thrust back she pushed her finger deeper. I reached my hand down and rubbed my clit. I don't think I've ever been so turned on.

It wasn't long before she was able to push her finger in all the way. He'd been watching her finger fuck me in the ass and gently running his finger tips on my back while he masturbated.

"Want to try anal?" he asked as she continued to finger my ass.

My heart skipped a beat . I was excited and terrified at the same time. I've wanted to try anal with a man. I've fingered my ass while I've masturbated and her finger in my ass felt real good.

"You're dic is a lot bigger than a finger." I told him. "I'd like to try, but you have to stop if I tell you to."

"Always." He replied.

Sliding her finger slowly out of me, she said "I have a thought that might be fun. Get up on your knees, Sylvia."

At first I got on all fours, but she pushed my head down on the bed leaving my ass sticking up. I couldn't see much in that position, but I could see her suck his dic then put some lube on it. She then put lube on my ass.

He got on his knees behind me. My heart was pounding with excitement and a little fear, but I trusted him. I've fucked him several times and he has never hurt me.

"Ready?" he asked.

"Yes," I said meekly and took a deep breath and held it waiting to see if it was going to hurt.

"No, no, sweetie, " She cooed, "relax, breath."

I relaxed and and took a few slow, deep breaths. I felt the tip of his dic touch my ass hole and tried to stay relaxed. He pushed the tip of his dic against my ass hole. It made me shiver with excitement. I waited for him to slide it in, but he just kept poking my ass hole. It felt good and I tried to push my ass back to make him push his dic in me.

She put her hand on my ass to stop me, "Not yet, sweetie."

His dic kept poking at my ass hole and jerking around. I couldn't see what they were doing but she'd giggle occasionally.

I was starting to become inpatient and thought to myself, enough teasing. Put your damn dic in me. I strained to turn my head to see what they were doing. "Are you jerking off on my ass?"

She answered, "no, I'm jerking him off on your ass."

He started making a sound I recognized. He was about to cum. He pushed the tip of his dic in my ass hole just enough to squirt his load in me. I had forgotten to remind him to put on a condum, but I didn't care. I was so turned on all I wanted was to have his dic deeper in my ass. I pushed my ass back onto his dic. This time she didn't stop me.

I felt his dic throbbing as I pushed on it forcing it deeper. I moved slow. It hurt a little, but felt good too.

She started rubbing my clit, "This looks so hot."

He didn't thrust into me and let me take it as slow and deep as I wanted. I pushed my ass back taking his dic deeper, but it started to hurt so I stopped and pulled forward.

I was breathing heavy and real close to cumming. "There, that's all I can take, but it really feels good."

He must have made a mental note of how deep he was because when he started thrusting he never pushed any deeper. It was a new sensation for me, he fucking my ass and her rubbing my clit.

I had an explosive orgasim and pushed my ass onto his dic until it started to hurt. I was still coming when he pulled his dic out of ass and rolled me on my back like he was tossing a rag doll. She quickly lay beside me and kissed me while his tongue found my clit.

After I caught my breath I asked, "How much did I take?"

He said, "I got the head in before you stopped, but you took most of it when you started to cum. I didn't want to hurt you so I pulled out. "

I kissed him and said, "Thank you. "

I'm not as naive as I used to be.


TrucknLuvn 59M/41F  
1622 posts
4/7/2016 1:21 pm

Anal is hit or miss for me. Some days, I have no problems and Joey is able to go to town. Others... well we don't get very far with it.

My orgasms from anal are very intense though. Some of the best orgasms I ever had involved anal.

♡Jess: The Trucker Babe

♡♡♡

Want more? Be sure to check out my blog: TrucknLuvn!


funintatown 41M
39 posts
4/7/2016 1:32 pm

hot story


forgotforgetting 57M
8134 posts
4/7/2016 2:11 pm

That's an awesome first experience. Congrats!

“Be yourself; everyone else is already taken.”
― Oscar Wilde


CuriousCpl6774 56M/50F  
183 posts
4/7/2016 4:16 pm

That's a very sexy description of your experience. Glad you enjoyed it.


oksylvia1992 32F
127 posts
4/7/2016 6:22 pm

    Quoting TrucknLuvn:
    Anal is hit or miss for me. Some days, I have no problems and Joey is able to go to town. Others... well we don't get very far with it.

    My orgasms from anal are very intense though. Some of the best orgasms I ever had involved anal.
What is different when you enjoy anal and when you get don't very far? Is it you how relaxed you or how turned on you or something different?

I'm not as naive as I used to be.


wrMercury 46M
1570 posts
4/7/2016 8:02 pm

Glad he took it slow and respected your limits


ShipwreckedinAZ 58M
341 posts
4/7/2016 9:16 pm

MMMM It is so enjoyable for those that have broken into anal properly. I have known to many that were pushed to fast or not enough lube. Your couple definitely took care of you.... VERY HOT!!!!!!!!!!!


TrucknLuvn 59M/41F  
1622 posts
4/8/2016 4:15 am

    Quoting oksylvia1992:
    What is different when you enjoy anal and when you get don't very far? Is it you how relaxed you or how turned on you or something different?
How relaxed I am is the biggest difference maker for me. Arousal makes a difference, but not as much for me anyway.

Also, my guy is well-endowed and when he gets extremely aroused, he gets very rigid. That also makes it a little more difficult for me.

♡Jess: The Trucker Babe

♡♡♡

Want more? Be sure to check out my blog: TrucknLuvn!


ruleher101 57M/53F
201 posts
4/8/2016 6:04 am

in time and more anal sex,get does get easier and before you know it,you will take the whole thing.


forgotforgetting 57M
8134 posts
4/8/2016 10:52 am

Like all things, there is a time and place for it. Even pleasureable things have a timing. By respecting this fact pleasureable things will remain as such. It seems prespective and moderation are the keys to a long and happy life. It took 40 years and dozens of fortune cookies to figure that out. LOL

“Be yourself; everyone else is already taken.”
― Oscar Wilde


44coyote2 50M/51F

4/8/2016 10:32 pm

Oh my god Sylvia, that was hot! Thanks for sharing sweetie.


MomoBear1 73M/109F
345 posts
7/19/2016 1:02 am

Soon you wil be enjoying anal like I di with both husband and his friends, First time 3 years ago I was frightened but after he did real gentle, I was soon pushing back to get his cock all in my ass


Become a member to create a blog