My First Time

My First Time: Male, 25, Connecticut

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Having lived with depression for a little over a decade, sex had just never happened. I only came close to dating someone once and I was too possessive with other girls to really allow anything to blossom. I just didn’t understand what “I” was doing wrong. That sadly came after.

Having failed to move out and being rejected for college, I decided that I would end everything. I was tired of living and would go out with a bang (no pun intended). I quickly found an online directory for escorts in my area.

I picked out someone who I deemed suitable, called her up, and arranged a meetup within the hour. After I had did that, a sinking feeling took over me. I was breaking the law and setting myself up for more self-destructive failure.

Realizing that I possibly made a mistake, I still convinced myself this was the only way. I drove to the hotel, donned my hood, and walked to the room she told me to meet her in. I knocked and then began to hold my breath.

She opened the door and quickly pulled me in. After asking if I was involved with law enforcement, she took her pants off and told me to get ready on the bed.

Instead of leaving, I simply just toughed it out. I asked her for oral sex and then gave her a fake name. After what seemed like forever, she complained of mouth cramps and I began to feel bad. I didn’t want her to suffer for my ignorance about sex.

So I told her that I would like to take her doggystyle. She complied with the request and climbed up on to the bed. Propping herself on her knees and with her buttocks in the air, I placed my hands on her hips and attempted to insert myself. I couldn’t figure out where to go.

She looked back with an inquisitive face and I just said, “I haven’t done this in a long time.” I felt like such a pathetic fool. After she helped me inside of her, we both thrust for around 10 minutes before she stopped. Turning back and asking if I had come, I told her no. This was when she got serious.

Needless to say, I came very quickly after that. After, I went to the bathroom and felt ill. I wasn’t sure why I thought this was the way to lose my virginity, but I took a plunge off the deep end. After thanking her and getting to my car, I sat in silence for a few minutes.

Not wanting to die anymore, I quickly resolved to get myself help. Even with that help, I still managed to get mixed up with escorts a bunch of other times. I was just too afraid to accept that I was too lazy and stubborn to allow a girl to know me.

Therapy has helped a considerable amount, but I have not been in a real relationship yet.

We’re looking for stories about the first time you had sex. Email with 500-1000 words. (Don’t worry, we won’t print your name — but please do make sure to include your gender, where you were, and how old you were.) Submissions may be edited.