Hey everyone this is going to be a long winded one, I’ll put a TL;DR at the bottom.
So about a year ago 22 year old me was having some issues. I was in a long term relationship with a woman I loved, but she was not interested in sex. Back in high school I had lost my virginity to her and we were pretty sexually active until her Sophomore year of college. A lot was going on and I understood. But, that didn’t change how horny I was. I didn’t want to look for someone else and I was sure any female friend I asked for a sexual favor from wouldn’t keep it quite.
So…I looked for an escort. After a few days of looking through web ads I found one I thought would work. She was attractive, plump C cups and a thick ass as well as around 10 years older then me. She also always used protection and as the two biggest fears I had where contracting a disease or being found out, I figured she checked all the boxes. After a light screening we set up a meeting at a local hotel. At this point I’ve got major nervous shivers. I’ve never cheated on my GF before and I’ve never had sex with anyone else. About an hour later, still shivering I pull up to the place and she waves me over. She looks good in person as well, wearing a sweater to cover her lingerie.
She can tell I’m nervous as I sit on the bed, letting her count the tip. “Are you cold?” I smile a bit and say no. “Is this your first time?” My mind shoots back to my GF and I feel a pang of guilt. “First time like this.” She nods and smiles, tells me to relax and that she’ll take good care of me. I take my clothes off and try to relax on the bed as she gets the condom ready. My cock to my horror has never been so limp. She doesn’t seem to mind and puts the condom on. “Nervous?” I nod timidly. She smiles again and begins blowing me. She had amazing skills and admittedly is better then my GF ever was. However, I’m not getting hard. My nerves and the fact that my GF and I almost entirely did bareback made it so my little bitch cock couldn’t get hard. I’m white so at max I’m close to 7” but at that moment i was 1 inch of pure soft.
I had an hour with her so she continues to work on me for a good 15 minutes, but the most I can muster is a half chub that can’t do anything. She gets flustered at this point and asks if it’s her. I embarrassingly tell her the actual reason and she nods. She continues for another 15 min but we still aren’t getting anywhere. At this point I am too embarrassed to continue and she is thoroughly flustered. I tell her that it’s okay, we can stop and she nods, apologizing as well for not getting me there. We get our clothes on and exchange an awkward hug. We say goodbye and as I am driving home I vow to myself that I’ll meet her again and show her what I can do, like an idiot who feels like he needs to prove himself to a lady of the night. I get home well before my GF. That night I feel awkward sleeping next to her after what I did. But soon enough that wears off and I start thinking about proving myself to that woman.
I eventually did meet her again. If y’all want to hear about that let me know.
TL;DR Hired an escort for the first time and because of nerves I couldn’t get it up. I vowed to prove myself the next time we met.
Source: reddit.com/r/gonewildstories/comments/dk94m5/my_first_time_with_an_escort
Part 2