Me And Dolly

I had a good friend in HS that people used to call "Dolly" in reference to her humongous boobs. We were in an active church group together so we were around each other all the time. She and I and another friend hung out because we were in the same parential situations so we just sort of gravitated to each other.

I was around her so much I didn't obsess over her boobs, probably because I saw them (clothed) so often. That might have been why she liked to be around me, since I was probably the only guy she knew that didn't stare at her boobs and just treated her like a regular friend.

She was blond, which didn't help with the big boobs assumptions, and probably not the sharpest tool in the shed, so it all added up to the big boob blonde airhead picture. But she was really sweet and would do about anything I asked of her. Of her assets, I probably noticed her soft full lips as much as her boobs.

I was pretty naive back in the day and a church going gentleman, so it rarely crossed my mind to try to take advantage of her. Looking back at situations she put us in alone, I think she wanted me to. Like working on Christmas parade floats alone at a secluded warehouse for many weeks. She would always decide when she knew no one else would be there that "we need to go work on the float".

One night we were both at church and she asked for a ride home. It was on the way and I didn't mind. Once we got in the car I don't even know how the subject came up, but we ended up going parking. We found a secluded spot, kissed a lot and after unleashing her industrial strength massive bra, I finally fondled those soft huge boobs. She said they actually were as big as Dolly's and she was very proud of her 36-24-36 figure. She was hot.

I played and sucked and tweaked nipples and we loved every second of it. I finally got to her pussy, she was dripping wet, but the odd thing was, she was so tight I could barely just get my one finger in her. She loved it when it finally slid in, but I was thinking, ummm how is this going to work???

She pulled my cock out and stroked me for awhile. We didn't know anything about oral back then, it was just fingering, groping and kissing. After awhile she gave me the go ahead to fuck her.

I layed her back and started rubbing my cock on her pussy, it was sliding around nicely between the lips and we were both loving it. I finally tried to push it in and it was like trying to push a giant summer sausage into a straw. I'm not super huge, but it is about 6-7" long and it is very thick, a gf measured the mushroom head around 6". It just wasn't going to work, not even hardly worth the attempt.

I tried and tried and we were both crazy horny. I knew if I ever got it in she was so tight I probably would have cum in 15 seconds. If it wasn't her first time it was close. But I didn't want to hurt her or make it a bad experience, so I finally stopped and said "I don't think it's going to go in, its too big".

We stopped, both frustrated out of our minds, got dressed, kissed and groped some more and I took her home. Worst case of blue balls ever, lol. We had one more memorable session. After school was out for the summer she went with me on a sports trip I had to drive to. She decided to lay down in my lap while we were driving on the highway, I unhooked her bra and played with her boobs the whole way and she stroked my cock. I'm sure several truckers we passed had a good day, and she enjoyed them seeing her and honking.

She ended up marrying some dorky guy. I think she's told him everything because to this day he still acts like he hates me and forbids her from talking to me. I guess he thinks it's on her bucket list for us to finally fuck. I ended up marrying a girl with even bigger boobs. But, unfortunately she doesn't have the lust for sex like Dolly did, fun to look at though.

I know if Dolly and I ever got another chance I wouldn't say no. And we'd find a way to get it in this time...