[MT] The Summer of Serra

My sophomore year of college I was in a bad place. My girlfriend of almost 6 years had cheated on me with one of my cousins. She was my first real girlfriend, my first kiss, lost my virginity to her, I had assumed we’d eventually get married. I was drinking too much, and my grades were suffering. I was basically a zombie going from class to class, present in name only, and it truly felt like it was only a matter of time before I either dropped out or was kicked out.

Then I met Serra.

We had randomly been paired together on an assignment, which I wasn’t excited about. I wasn’t in the mood to be a ‘team player’, I didn’t want my depression to ruin anyone else’s grades, and I wasn’t the most outgoing person. However, what I lacked in motivation and personal skills Serra made up for tenfold. She was this walking ray of sunshine and optimism and evidently saw what a mess I was and took it upon herself to “fix me”. We quickly finished the assignment together, but began texting and hanging out more and more, the haze began lifting, and it was obvious we had feelings for one another.

I eventually mustered up the courage to ask her out, and received an emphatic yes, to my relief. I’ll never forget when I first saw her walking into the bar where we had agreed to meet. She was much shorter than me, about 5’3″ with shorter wavy blonde highlighted hair and big brown eyes, usually sitting behind glasses. She was slightly chubby and pear-shaped, holding some extra weight in her thighs and butt, but she carried it extremely well in my eyes. That night she was wearing a light blue floral sundress and just looked like…happiness.

We had a few drinks, working through our nervousness, started flirting more and more before she abruptly got serious. Clearly nervous, she revealed to me that she was indeed MtF trans, and had never told me for fear of scaring me off.

Now, this blew my mind. I had zero experience with any of this having grown up in a deep red, very rural, very conservative town. I always considered myself straight as an arrow and never even questioned it, but I quickly came to the conclusion that I genuinely liked (maybe more) Serra, and that’s really what mattered.

We continued to drink, a whole *new* set of nerves to deal with until we eventually started to get handsy, which led to making out, which led to us climbing in an Uber to her apartment.

We collapsed onto the couch, continuing to make out for a while. I climbed on top of her, pausing for a second when I felt our hard cocks pressing against one another, still unable to process all of this. I more or less decided now or never and sat us up, running my hands up her dress, pulling it off over her head. She had not worn a bra, her small breasts slightly upturned, and she had on a pair of lacy pink boyshorts that had an obvious bulge pressing against the fabric.

I tenatively reached over, her eyes watching my closely as I pressed my hand against her cock as she sighed softly. I could feel her throbbing against my hand. I began rubbing her slowly, leaning in to run my tongue over her nipples as she impatiently reached down and slid her panties down, quickly followed by my shirt. I looked down and saw her cock for the first time. She was slightly below average length wise, but was pretty thick, smooth and pink.

I gently wrapped my hand around her and began to stroke, pleased at the sounds she was making, my free hand running up and down her amazingly thick thighs and legs. After more than a few minutes of my stroking she leaned in and whispered in my ear “Use your mouth”.

Seemed like a fine idea to me.

I did as she said and got on my knees between her legs and without hesitation wrapped my lips around her cock, sliding my mouth around her thick shaft, my hands on her thighs. I felt Serra’s hands running through my hair, encouraging me with her moans as I began working my head back and forth, trying to remember all the things *I* liked about getting blowjobs: running my tongue around the head, using plenty of spit, etc… Her short length let me take her entire cock in my mouth, barely hitting the back of my throat.

I kept moving, her moans and whispers beginning to get more persistent until I finally hear her whisper “I’m going to cum”. In a move I still regret, I pull her out of my mouth and continue to stroke her, watching her tense up and shoot a big load of cum all over her soft belly.

We cleaned her up and she repayed the favor and we ended up falling asleep together on the couch. That night lead to a summer together where we did things to one another I never would have pictured myself doing. We began dating, moved in together, eventually graduated, moved to a new city together, and are still together to this day :)

Thanks for reading all of that!

Source: reddit.com/r/gonewildstories/comments/8niew5/mt_the_summer_of_serra