My Very First Time Having Sex With Another Woman

I wrote this shortly after my first lebian experience a little over a month ago, to an online friend of mine. . . (I'd been on the 'look out' for a woman to have my first lesbian experience with for about a week)

At dinner with mom and my uncle, I noticed a waitress who was very attractive. (NOT our waitress, some other waitress) She noticed me noticing her, if you know what I mean. We exchanged several glances and smiles. As we were leaving I went to the bathroom to pee and she was in there. She hit on me big time! She told me she got off at 11 and would I like to maybe meet for drinks. I told her I'd think about it and I might meet her in the parking lot @ 11.   Mom drives me all the way back over here, I hop in my car and drive all the way back over there and arrived right at 11. We go to a little out of the way place she knew and ordered drinks. After one drink and some very intimate conversation I agreed to go back to her place. (she rode to work with a friend, so we were in my car). Out in the parking lot, she leans over and kissed me and ran her hand up my dress to my p  u  s  sy. WOW, what a kisser she was!. . . Here comes the unbelievable part - wait for it, I still can't believe this happened....   VERY nice apartment. We make out and do the petting thing and eventually got in the shower. I told her what I wanted, that dominating thing and how I like it in the  b u t t...  She ties me to the bed doggy style and blind folds me. She straps on the most incredible ***** I've ever seen and starts working me over and talking all this sexy stuff to me. And then she starts eating me. OMG, fan-******* i n g-tastic! I've NEVER had somebody lick and tongue my butt hole before! Several ******* later I was as turned on like nothing ever before. I was begging her to please f uc k me. I can't remember EVER being so turned on! She gets off the bed and picks up a tube of a new lubricant she picked up. (I later found out it's called 'desensitizing' cream).   She gets back on the bed behind me and put the cream on her hand and then to my butt hole. Keep in mind, I'm still tided and blindfolded. I thought she had poured molten wax on my butt hole. It was like lava! I let out a scream that I'm sure the entire complex heard! It's like 2am and I'm screaming like a blow torch had been put to me. She starts screaming, jumps up and runs to the bathroom and grabs a towel and soaks it with water and comes running back to me. I'm crying my eyes out, struggling to free my hands, which I did, and pulled off my blindfold. She behind me now soaking my crotch with the wet towel and we're both crying now. She's crying and begging me to forgive her and she's telling me she had no idea it was like that. I could tell she was telling me the truth and I forgave her and within 20 minutes or so, as odd as it sounds, we were laughing about it.  So, we're laying there together in bed and reading the back of this tube of desensitizing cream. It said that if a burning sensation occurs to 'see your doctor'. WTF?!?! What if your butt hole burst into flames?! What do you do then?! It's funny now...real buzz kill last night let me tell you. We ended up cuddling and fell asleep.    We took a shower this morning and afterward I finally got to go down on a woman for the first time! OMG, it was amazing! I loved it! But (butt...LOL!) frustrating, very frustrating. My bottom still stung and I wouldn't let her do me. I really wanted to ***, so I let her finger me while we made out. We made plans to get together tonight again. I'm probably going to call it off though because my butt still stings. I mean not fire like or anything, it just still stings some.   This story is NOT over....   I get home at about 9am this morning and there's my mom in my driveway...and two cop cars! She's completely freaked out! Goes all p i s    sed off at me. Demands to know where I've been. We get into this big shouting match. We go inside, the cops leave (after canceling the APB on my car...OM effing G!). When mom dropped me off she 'claims' she said "I'll be back over in a little bit." and she claims I said "OK". I guess I was completely zoned out on getting back over to Scottsdale. I was only inside for a few minutes after they dropped me off, grabbed my car keys and took off. . .  left my cell phone on the kitchen table. ****! Mom took her brother back to his motel and came back and waited. . .and waited....and waited.  So this morning after we calmed down, having coffee, I told mom where and what I'd been up to. (yes, she knows I'm looking for a lesbian girlfriend - LONG story how she found that out) She demanded to inspect my butt. I let her. She went and got some ointment and I've got that on now. Feels a little better. She insists that I go and see a doctor tomorrow about it. I dunno, we'll see how it is in the morning. . .   I logged on and now I'm sitting here telling you all this. . . crazy huh? Un-******* i n g-believable! 
JessieFoxxx JessieFoxxx
31-35, F
17 Responses Oct 15, 2010

Sounds amazing, I wish I could find a woman like that. I'm just knew at this whole lesbian thing but I think I've known for years that I'm more attracted to woman then men.

The first time you have sex with someone of the same gender is as amazingly unique and good as the first time you ********* inside someone of the other gender (if you're male) or get ****** (if you're a female). I wouldn't be able to live without having sex with both males and females.

I had a first time I was so unbalivable I was scared. And know I watch other lesbans have sex

you are a very lucky person,

Michael, I love me some Applebee's. Don't eat there a lot, but when I do I've always enjoyed the food. I hope your waitress was sexy. (Don't you just adore sexy wait staff?!) People who are rude to wait staff are pieces of **** and those who stiff them are even worse! And if you've not guessed, yes, I've waited my fair share of tables. Yeah, Miss Attorney Smarty-Pants (one of my moms many nick names for me) waited tables; Is there a problem with that?! I didn't think so. . . .LOL (I was a damn good waitress too! Rarely wrote orders down, and rarely got something wrong. But yeah, it happens. It happens. Chill. It's not the end of the freakin' world! Uh oh, somebody got me up on a 'high horse', hard to get me down once I'm up here! (Way to go Michael!)<br />
Did I find a better desensitizing cream?!?!? I cringe when I even THINK about the stuff! I don't want to even imagine what I'd do should I actually SEE a tube of it again. No, never used it before, will NEVER (ever) use it again. "But Jessie, it works so GOOD?" you may say. . .<br />
Really?! Then why dontcha stick it up your OWN ***. Been there, done that. NO THX!"

Charles, I did NOT see her again. She said she would call, she never did. I called her, left several msgs before realizing she probably just wasn't interested. Kinda sorta hurt, but I got completely over it. It WAS funny. . . my mom is still having fun with it. Her and Jackie like to gang up on me and have a little teasing fest ever once in a while...I can take it as well as dishing it out....<br />
Thx again for your kind words!<br />

Lol, wow!! great story..and the thing about your mom, also very funny..

Holy sh*t that is hilarious! I can't believe that happened to you! But hey, you enjoyed it, that's the important thing.<br />
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Still X-D Wow!

Ahhh...loved the story! I laughed so hard! Wish I could experience that...without the lava butt of course!

Why do I find this arousing ?

There IS more, sort of a 'side-bar' if you will. Mom and I go to the lake a lot. (Dad died when I was a little girl) Mom & Dad were always big time boaters. Mom has always had a boat. We love it. Anyway, lake life has always been a part of our lives. Mom is in her early 60's and is a beautiful woman. She works out regularly and eats proper, a very sexy woman for her age. I found out at the start of the summer that Mom is (and always had been) bisexual. She's had lots of boyfriends over the years, they've come to the lake with us. She's also invited lots of her other friends as well. Hell, we both have. Anyway, I found out that several of her women friends were in reality her lovers. How did I found out?<br />
It was very late in the evening, I was sleeping on the deck of the boat (we were beached and had set up a little camp on the shore). I woke up having to pee. As I started to sit up I heard some noise and peeked over the side and saw my Mom's girlfriend going down on her. Mom was sitting in a lawn chair, legs spread wide, stroking this ladies hair as she did her thing. "OM-Fing-G!" I thought. Way too awkward of a thing to just interrupt like that. I laid there and like the proverbial 'train wreck', couldn't help watching. Then I watched them switch places and watched my mom go down on her! I just couldn't believe what I was watching. "My Mom is a lesbian?!?!" I kept thinking (and watching). This woman she was with was not too much older than me, maybe 40. I ended up peeing right there where I lay in the boat.<br />
I waited until we got home and were alone before I asked her about it. It's not at all like I disapproved or found it gross or anything. I was just dumbfounded that I was completely in the dark about my mom's true sexual nature. And she told me that afternoon "Don't knock it till you've tried it." And THAT is what inspired me to at least try it. I'd been fantasizing about it for years, and finally did the deed. The story you read was how that all went down.

OMG! I love had me laughing out loud! Truly a priceless story! I'm glad you had the wonderful experience, thank you for sharing.

nice it! :)

I love your story baby doll! :)

The first time is always something to remember if it is something you have been anticipating for a while. Yours had a few unexpected moments that will make your first time memory seriously unforgettable. Thanks for sharing... it was a great read!

Lol. Funny.<br />
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Great story. My first time (ever) and my sister and her husband showed up at my door completely unannounced. Just because. Way out of there way...just because.<br />
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Spent the last 16.years with her though :)