Lesbian Tomboy Stories

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Tomboy Makeover Pt. 01

by macktosh on Apr 23, 2019
Lesbian Sex

"Ahh... ahh..." She sneezed explosively, making her two friends start away from her on the couch and giggle. "Jeez, Alex, warn us next time," Sophia said, grinning. Alex rubbed the back of her neck, a little embarrassed. "Sorry, but you've been tickling my face with those brushes for an hour. It's been building up." She reached up to wipe at her nose with...

Tomboy Makeover Pt. 02

by macktosh on Apr 23, 2019
Lesbian Sex

Thank you for all the positive response to the original, it inspired me to write this. Hopefully it makes for a decent continuation. Also, thanks to LaRascasse for helping me with this. Alex ended up sticking her head under the shower to clean off and rubbed her hair into a mess of damp spikes with a towel before hesitating at the door. Now that she thou...

Bikini Wrestling Bet

by eh001 on Dec 27, 2020
Lesbian

So you might be wondering how a tomboy like me ended up in a bikini wrestling competition. Or not. Either way, I'll tell you. When you're 20 years old and a sophomore in college, you'll take on just about any opportunity to pay off your tuition. And your books. And all the other little expenses they throw in there just to suck your money dry. I was honestly...

Somali Lesbian Tomboy Files

by Samuelx on Sep 16, 2017
Lesbian Sex

When I feel horny, most of the time, like the rest of us, I masturbate like crazy. That day, though, I had really bad. I sat in a washroom stall in the women's locker room inside the Capital University campus gym, and fingered my already wet pussy to a guilty pleasure. Got to enjoy the simplest things in life, you know? Anyhow, in case you're wondering who t...

A New Beginning

by CaroleS32 on Sep 14, 2017
Lesbian Sex

I have always been a bit of a tomboy. I like to wear my hair short because it is easier, and I think it flatters my round face and brings out my bright blue eyes. I am rather short at 5’1”, and weigh 140 pounds. Some people would say I am a little stocky but I am not fat just muscular. I have a rather large 38c chest, which on my short frame appears even lar...

Strange Day

by Angelus on Sep 14, 2017
Lesbian Sex

For as long as I can remember I have been classed as a tomboy for several different reasons. The two main reasons are the way that I dressed and that I looked like a boy. I don't have the facial hair and deep voice of one but I do have that sort of face, short hair and that type of body, in other words I did not have any breasts to speak of. No boy used to l...

Something

by BitterIchor on Sep 13, 2017
Lesbian Sex

Serenity Walker walked along the halls of the small town high school with her shoulders slumped and a tired look in her eyes. The last few weeks had been very taxing. The 18-year old petite, short-haired brunette tomboy high school student had been outed two weeks ago in front of at least 20 people. She dropped her diary earlier that day, and by a cruel twis...

Black Slave Woman Ch. 07

by Samuelx on Aug 30, 2017
Lesbian Sex

My name is Estella Barnes. A six-foot-two, blonde-haired and green-eyed, chubby and big-bottomed, somewhat tomboyish Irishwoman living in the city of Chicago, Illinois. I'm an intern from the University of Illinois working for the Opal Winston Show. Yes, the Opal Winston Show. I can't tell you how excited I was to work for the show. I've always loved Opal Wi...

Somali Lesbian Diaries Ch. 05

by Samuelx on Sep 16, 2017
Lesbian Sex

What's up people? My name is Nadeeya Osman, Somali-Canadian Muslim, die-hard tomboy, proud lesbian and student-athlete residing in the City of Ottawa, Ontario. The other day, I went to the City of Montreal, Quebec, for a university basketball tournament and while I was in la belle province, I had some unexpected fun with my teammate Afaf Lahoud, a Lebanese c...

Strange Day Ch. 02

by Angelus on Sep 13, 2017
Lesbian Sex

My name is Sarah Jamieson. As you can remember I am eighteen years old and a very late bloomer; so much so I was a tomboy up until this day; the one that started out so very strangely. As I walked away from the gym I could not get my head around the fact that my first sexual experience was with a girl in the school. I knew that fact alone should make me wor...