The love of my life, and the time I took her anal virginity [MF]

I’ve gotten a bit of hate for the first few stories I’ve posted about my experiences being the “other man” so I figured I would take a turn and instead tell you about the one who got away.

Like any good epic, I’ll start *in media res*. For background, I’m 6’2″, a former college athlete, with brown hair and dark eyes. I was in my mid-20s at the time.

What you need to know about Jess boils down to one simple interaction. We had dated off and on for years, since high school in fact, but it had never stuck. The first time I met her was almost biblical – she walked into the room I was in and I was struck deaf. It sounds ridiculous, but as she approached me (we had been set up by mutual friends) I heard nothing, saw nothing, thought nothing aside from her stunning eyes and her beautiful face.

She was tall, 5’10”, and a former model who chose college over NYC contracts. This story comes years later in our relationship, after that first meeting. We had dated in high school, and at the beginning of my college years (I was a year older) but broke up due to the distant. This story finds up the beginning of the summer after my sophomore year.

She had reached out, asking if I wanted to hang out and catch up. I had to run a few errands that afternoon and told her to meet me at our local mall. As I stood in the entry way by the parking lot playing on my phone, I had the thought that maybe she wouldn’t show. Ever so slightly I felt a finger tip, and then two, and then a hand place itself gently across my lower back. Her hand slid across my back, and was soon joined by her chin on my left shoulder. “Hi” she whispered, her breath tickling my ear, before I turned around and engulfed her in a hug.

There she was – my muse, my love, my… Helen of Troy – standing in the flesh. I grant I never saw a I goddess go, but in that moment, my heart was displayed before me. I felt complete again.

We wandered the mall for hours, talking about everything and nothing. We slipped into an all too casual familiarity, as she helped me pick out jeans and I dresses for her. As darkness fell, the night began to come to end. I walked her outside, to her car, and experienced the awkward lingering of two lovers who don’t want to say goodbye. Neither of us wanted to be the first to break the peace, to kiss the other, and so we said goodnight.

As I pulled my seatbelt on I received a text – “meet me at our old spot.” I didn’t need to be told twice. As I pulled into the back parking lot of the strip mall down the road my memory was flooded with special nights – our first kiss, among others. This had always been the place we could hide out from the rest of the world and be alone in thought.

As I pulled up next to her car she got out, leaning against the back left door of her SUV. I got out of my car and walked around the back and we met lips first, devouring each other between our cars, under the moon.

We soon climbed into the back of her SUV, me sitting in the middle of the bench seat and her on my lap. As we shed our clothes we began our usual refrain – lamenting that she was still a virgin and that we had never had sex. We had talked about anal before, and I had played with her ass, but we had never tried it.

After we were both stripped nude, she sat on my lap, her back leaning against my chest and her pussy sliding up and back against the length of my cock. As I whispered in her ear, I pinched her nipples and ground my hips into her, teasing her slit with my tip. As I reached down to rub her clit she grew exasperated and looked over her shoulder and said “Can we just try my ass?!”

She didn’t need to tell me twice. I asked about lube, and she started looking through her purse for options. We ended up with, and I swear this is true, carmex of all things. Not ideal, and I wouldn’t do it now, but at that age and level of horniness it worked for us.

As we made out she jerked me off, spreading the carmex up and down my cock. She turned around, head bent against the roof of the car, and slowly lowered herself down until my tip rested against her tight ass. Slowly, stutteringly, she pressed herself down as my tip slid into her ass. She stopped and moaned, and her legs shook, and then she lowered herself further down.

Eventually she bottomed out, taking all of my cock in her ass. Between whispered promises of love not forgotten and groping hands along my hair and her tits and her clit, we began to work up a rhythm. Before long, my passion overcame me. I knew I wouldn’t last long, and I whispered in her ear that I was going to cum. Her response was to double down and she started lifting herself off me before impaling her ass on my cock. As I started to cum I pulled her tight, sliding as deep into her as I could, biting her shoulder and moaning sweet nothings into her ear.

After my cock stopped twitching she sat up and moved off of me to the seat next to me. I pulled her close and we cuddle in the back seat of her car as the early morning hours passed. It was the first night of another of our stents together, and one of the moments where I knew that she was my soulmate.

Source: reddit.com/r/gonewildstories/comments/j3myfd/the_love_of_my_life_and_the_time_i_took_her_anal