When I was 19, I was a freshman in college still getting over the heartbreak of things not working out with my high school sweetheart, and it was especially painful for me when Valentine’s Day rolled around for obvious reasons. Because of her religion, we never had sex, and I felt an intense longing to lose my virginity, but I’ve never been the best at engendering relationships with the opposite sex, so the thought occurred to me to hire an escort for the occasion. So I went to the escorts section of Backpage (it was still a thing back then) to find one who I liked.
I eventually settled on a curvy 26 (or so I thought) blonde named Taylor (which was just an alias) and sent her a text asking to schedule an incall. We scheduled a 30-minute one (which was all I could afford) at the Quality Inn where she stayed for 2:00 PM that day after I got out of class. Because I didn’t have my driver’s license yet, I had to take the bus all the way to the other side of town about 5-10 miles and walk an additional stretch in the pouring rain to get to the hotel. When I got there I sat in the hotel lobby only to get a text from her saying that she’d be late because of work and that she had to delay our little get-together until 3. So I went and dinked around in the nearby library for an hour before then, and she texted me her room number and I went up to it and knocked on the door.
When she opened the door, I was a bit thrown off at first: she looked quite a bit older than what she advertised as and was a bit rough-looking (but not enough to send me packing). To give a mental image of her appearance, she looked a bit like actress Laurie Holden (Andrea from *The Walking Dead*¹). To but it bluntly, I was a bit let-down. Nevertheless, I figured I went through all the trouble to arrange this, so I better see it through to the end. We talked for a bit and I asked her her age, and she said she was 46. Then she asked me mine.
“19”, I said.
“Aw, you’re a baby! Most of my clients are much older than that.”
It was then that my apprehension turned into optimism, because I’ve always had the fantasy of seducing or being seduced by older women.
“Are you Jewish by chance?”, she asked.
“No”, I replied (I’m mostly Anglo and Swiss). “Why?”
“It’s just that you look Jewish”, she said.
“Do you have any kids?”, I asked.
“Yeah, three”, she replied. “I’m doing this because I need to provide for them after me and my husband got divorced. I’m in the Army.”
“So you’re a MILF. That’s wonderful. That’s been my fantasy for the longest time. Also, I almost forgot to tell you, I’m a virgin, so take it easy.”
“Don’t worry. I was once hired by my friend to take her son’s virginity before he was shipped off to the Army. It’ll be just like with Stifler’s mom.”
That quip really put me at ease and I was ready to get down and dirty. By that point I had stripped down to my underwear and was laying on the bed. She returned the favor by taking off the sundress that she had been wearing, lifting the straps off her shoulders and letting it fall to the ground, and I was astounded by what I saw. She had an amazing body: not too thin, but not too fat either with curves in all the right places, including a wonderfully juicy ass and breasts with pierced nipples that instantly made me aroused. She may not have had the greatest of faces, but her body was to die for and after my initial disappointment, I was now fully assured that I had made the right choice.
(I should also add by now that the conversations I’m describing are not 1:1 translations, but rather rough attempts to capture the spirit of what was being said.)
Before getting into things, she told me her rules, which were no cunnilingus, no anal, no kissing on the lips, I can only jizz once, and that I must wear a condom at all times. I’m actually embarrassed to admit that when she referred to the former as “[going] down on [her]”, I wasn’t sure what that meant and she had to clarify that she meant “eat my pussy”.
She started off by giving me a full-body sensual massage, gently running her hands over my bare torso in a way that started to get me really aroused. She asked if I’d ever had a girlfriend and I told her about my relationship with my previous. We talked for a bit about my experiences in college and where I was going with my life before she asked if I wanted a blowjob. I said yes, and she put on the condom and started sucking my dick. This was a completely foreign sensation to me, but my dick instantly got hard as if on pure instinct, especially since I had a good view of her gorgeous body and succulent breasts. I let her go down on me for about five minutes or so, and I just laid on my back, closed my eyes, and took in the sensation. At this point in time, I hadn’t quite figured out masturbation, as I hadn’t realized what climaxing felt like (I’d just fondle my dong for a while and get aroused), but I still appreciated the warm wetness of her mouth encompassing my meat stick, even with a condom. After that five minutes was older, I let her know I was ready for sex, and she got off the bed and dropped her panties. Up until now I had never seen a vagina in a sexual context, and seeing her silky smooth, shorn pussy at the time felt like I had just discovered the Holy Grail.
“So what do you want to do?”, she asked.
“Get on top honey”, I replied. “You do what you like.” (This was me quoting a Tenacious D skit)
So she climbed onto the bed as I was lying naked on my back, grabbed my cock, slid it in between her legs, and started riding me cowboy style.
My heart skipped a beat for a moment: I simply couldn’t believe what was happening. After all these years of what felt like missing out, where my only experience with sex was from pornography, I see this blonde, curvy, mature goddess straight out of my wildest fantasies looking down at me as we grind our organs together and thought to myself “Is this what heaven feels like?”. Despite having almost halved my bank account at the time to make this happen, in this moment, I simply did not give a fuck and it was the last thing on my mind. As I took in her gorgeous body, my cock gets even harder as I moaned in pleasure.
“Oh Taylor” I gasped.
She then took my hands and placed them on her breasts. I was aroused by her confidence. Right now country music was playing on the radio that she turned on, and to this day, I still remember the song that I lost my virginity to (‘Like a Cowboy’ by Randy Houser²). Her breasts were surprisingly firm, and I leaned up to diddle her pierced nipples with my tongue.
“Could you not do that?” she asked. “I just got them pierced and they’re still sore.”
I complied with her wishes and lay back down as she continued to ride me.
I then told her that I would like to try doggy style, so she dismounted me and got on all fours as I repositioned myself to enter her. I then got a good look at the large grenade tattooed across the small of her back: a hell of a tramp stamp if I say so myself.
“Be careful” she said. “I just got that tattoo and it’s still sore.”
I slid my cock into her pussy and it was then that I began to truly appreciate her bountiful booty, so round and juicy in my hands as I grabbed it for leverage. Now I was in control, and I thrust my cock in and out as it continued to engorge, the view of her ass as it slapped against my pelvis being an incredibly arousing sight. I started out slow to test the waters, and gradually upped my speed as she started to moan in pleasure due to the increased stimulation such a pace brought.
“I feel so dominant” I moaned in pleasure.
“Dominate that pussy” she moans back. “Your cock feels so good.”
She then started fondling my balls as I railed her from behind. She really new what she was doing.
Next we did missionary, so she flipped around onto her back as I leaned in close to her, supporting myself with my arms as I thrust inside her. Our faces were very close to one another, and I stared into her blue eyes for a bit before leaning in to kiss her on the neck.
At this point we had been boinking for about 15 minutes or so and I was getting tired from being on top, so I lay down on my back and asked her to mount me again, this time in the reverse cowgirl position. I took a hold of her hands, our fingers interlocking as she bounced up and down on my penis.
We continued to fuck in this position until I had about five minutes left in our session, at which point she was shocked that I hadn’t ejaculated yet.
“I’ve never seen a virgin last this long”, she exclaimed. “Want me to take the condom off and give you a handy?”
I accepted her offer, so she took off the condom and started jerking me off. It definitely felt different from sex with a condom, as her hand and my penis actually made contact without any sort of barrier between them. She did this for the remainder of our session, and I told her specifically to really focus on stimulating the head of my penis, but alas I was unable to climax.
“You should go to the doctor and get that checked out” she said.
When our 30 minutes was up, I put on my clothes and got ready to leave. She kept hers off, and I got to bask in her naked yumminess for one last time. Looking at her made me wish that I had more money to my name, because if I did, I would have forked over some more to go for at least an hour longer, rip my clothes right back off, pin her down on the bed with my hands, and have my way with her. Despite being a woman of traditionally ill-repute, I saw a kind, radiant, and nurturing soul that shined through her somewhat rough exterior and, in the words of a television sitcom popular on Reddit, took me by the hand and made me a man, as well as help me in living out my ultimate fantasy.
“Thank you”, I said as I leaned in to hug her and caress her beautiful body one last time. She gave me a quick kiss on the lips, which surprised me due to it being against one of her aforementioned rules.
I then exited the hotel room and caught the next bus back to campus.
To this day, I still think about that experience. Sometimes I regret paying for my first time, but I moreso regret never seeing her again. I’ve tried getting ahold of her via her cellphone, but her number was no longer in use. Most of all though, I cherish that magical 30 minutes in that hotel room for the near-magical experience that it was, and doubt that I’ll ever have one like that again.
Source: reddit.com/r/gonewildstories/comments/du74nc/losing_my_virginity_and_living_out_my_ultimate