Still not for teacher
I am approaching 20 years since graduating high school. Back then I had an English teacher who I had the biggest crush on. She was a beautiful Hispanic woman. I was always very careful not to reveal my crush or do anything to give it away because she was really fat. But the way she dressed and walked, her ass shifting side to side, her fat belly and big tits jiggling...I jerked it to her more than the entire cheerleader squad combined.
I guess you could say I was a late bloomer. I didn’t lose my virginity until age 20 and when I hit my stride I completely forgot about my teacher and never really had a thing for fat girls. I even made fun of them. I had a failure of a marriage and have over the years drifted from one woman to another. I do all right, generally fucking what most would consider hot and desirable women. I have a few with whom I enjoy FWB status on a recurring basis. I have a few married friends who envy the hell out of me. Their wives are all either fat or overbearing or both.
I think I’m in an enviable spot. So you can imagine my surprise when my crush on my teacher came rushing back in without warning. I was at a mall with a small group on Black Friday. We had done a “Friendsgiving” the day prior. I had ducked into a Starbucks with one friend and we were getting coffees for the group when I heard someone call my name.
There was my English teacher. Even after all these years she recognized me and I recognized her. I’m late 30s now and she’s late 40s. She had her daughter and a friend of hers, both mid 20s. I introduced her to my friend and we hugged. My teacher is still really fat. She must weigh 450 pounds. Feeling her pull me into her soft body and press those massive soft tits against me gave me an instant boner.
When we all got our order I told my friend to go on with the group without me and she gave me a bemused smile. My teacher, I’ll just call her J, told her daughter she wanted to catch up with me.
We sat and talked for over an hour. My friends and her daugter texted us intermittently and I told them to go see the movie without me. She told her daughter something similar. She mentioned she had taken a principal job at a school near where I lived and had worked there over 3 years. I had no idea (neither of us live where I went to HS and she taught and she’s not a social media type). She told me her husband left her. He was frustrated with her weight (she was fat when he married her) and fucked a woman on the side who was leaner.
Anyway we spent so much time talking that we agreed to go get dinner and some drinks. At one point during dinner I reached across the table and just took her hand and squeezed it. She squeezed back and didn’t release even after she eased up. We held each other’s hand and an incredible wave of excitement pulsed through my body. At one point she got up to use the ladies room and I paid the check. Then I waited for her outside the ladies room. When she came out I slid my arm around her waist and tried to pull her close to me. She reciprocated and after a brief and awkward pause we kissed. I let one hand wander down onto her immense butt and felt her hand wander down and grab my aroused cock. I kissed her again and asked if she wanted to go somewhere private.
I didn’t drive to the mall in my own car and her daughter’s friend had met them there so she asked her daughter if her friend could take her home. She drove me to her home and the next thing I know we’re in her bedroom and she aggressively kissed me, pushing me back onto her bed and sitting on me. I felt her weight on me and it was exhilarating. I was about to fuck a fat chick, and not just any fat chick, one who had been my teacher years ago.
We slipped out of our clothes. When her panties dropped I picked them up and rubbed them on my face. They were wet and smelled like her ass and pussy. It was intoxicating. She pushed me back into the bed and crawled into position over me, taking my cock and positioning herself. I watched and then as she lowered herself down her fat pussy just devoured my cock. She closed her eyes as she settled into place and again I felt her weight on me. I could believe I was doing it. I was inside a fat woman. I’ve never had sex with a chubby woman, much less a 450 pound whale like J.
She worked and positioned herself and focused and concentrated and when she climaxed I thought her fat pussy was going to suck me in. When she caught her breathe she leaned forward and smothered me with her fat tits and I started pushing my hips up into her.
When I felt myself about to cum i told her and she dismounted, put me in her mouth and finished me off. My cum joined her dinner when she swallowed me.
After that we drifted off to sleep, but I do remember waking up when her daughter got home. Daughter came into the room and kissed J on her head and said, “I love you mommy I’m happy for you.”
(BTW, her daughter isn’t fat at all. I’d love to hit that too but that’s probably just a fantasy. For now I’ll stick w her mom.)
We’ve spent a lot of time together in the ensuing weeks. J says she isn’t looking for a relationship and I never am, but this sure feels like one. I haven’t fucked anyone else, we come home and watch movies together and go to dinner together and stuff like that. Her daughter is used to seeing me at their home. The sex is amazing, but sometimes a little awkward and difficult. I’m not used to her weight. Or when I go down on her she has to press on her fat pussy or I won’t be able to breathe.
I am also thrilled to say I popped her anal cherry. That’s a story in its own right but it’s a little messy and probably not suitable to share. Despite the mess she wasn’t embarrassed at all and enjoyed it and we’ve done it several times now. It’s still a bit messy but she’s getting better. And it’s worth it.
I honestly have no clue where this is heading. Neither of us are looking for something serious and she’s about 10 years older than me anyway. And truthfully as fun as this is I don’t think I can commit to only being with one woman. Especially a fat one. For now I am just going to enjoy this for what it is and continue to enjoy the amazing sex I’ve been having with my old HS teacher.