Sorry for how long this is, but I didn’t want to edit anything out. It’s all so vivid a memory for me. If you’re looking to read a quickie, move along, but if you like detailed experiences, I had a good one I’d like to tell you about.
I’ve never told anyone this story because, well I had my own “Stiffler’s Mom” experience for my first fuck. I was 18 and just out of high school. I’d always been shy so I’d never really had a full time GF. I’d dated, sure, but it was mostly kid stuff. Nothing too serious and certainly no sex though I craved it like crazy.
The summer between HS and college, I had a job at the local Holiday Inn as a porter. I had a pager and I took care of guest requests for extra towels or broken TVs. I also delivered room service orders, such as they were. It was a motel by the interstate. Nothing fancy, but it was fun and I had some freedom. I wasn’t chained to the front desk.
I had plenty of crazy experiences there during my tenure, including being shot at and seeing a guy get shot by the cops. Tons of stories, but the loss of my virginity there is the best one. I was working one night until 11. Around 10, I answered the phone at the front desk because the clerk was busy. It was a sexy sounding woman who was a little bit buzzed. To this day, I have no idea why she called the hotel, but she did and I ended up talking to her for 20 minutes or so. She sounded sweet and her voice was making me horny so I kept talking.
At one point, she said, “You sound like a sexy boy. If I was there, I’d suck your cock dry.” I almost came in my pants just hearing that, so I wasn’t going to let this opportunity go to waste. I replied, “Well, if you’re serious about that, come to the motel and go to room 218. The door will be cracked open. Go inside and I’ll meet you there a little after 11 when I get off work.” I wanted to talk dirty to her but I was practically whispering so the clerk wouldn’t hear.
The woman, I’ll call her Norma, took the bait and made sucking sounds over the phone. Mind you, I had no idea what she looked like. I just knew she was a woman and she had a mouth and a desire to suck my cock. I honestly just wanted to know what that felt like after years of dreaming about it. I told her to be there and I hung up.
I sat there and just knew my face was bright red. My cock was like steel in my pants. I was so fucking stoked. I got busy doing all the tasks I had to get done before I left for the night. I was breathing hard and throbbing and sweating. I’m sure everyone noticed I had suddenly lost it, but I didn’t care. I was going to get my cock sucked for the first time!
Then it occurred to me. What if she wanted more? What if I wanted to fuck her and she let me? I didn’t have a condom! There was a gas station next door to the hotel that had those creepy condom dispensers in the men’s room. I ran over there with some quarters and came back with 3-4 condoms in my pocket. Who knew if they were even safe to use, but I had them!
When 11PM finally arrived, I tried to be cool and casual about it and left for the night. I got in my car and drove around the block to park in the parking lot that butted up against the motel lot. I didn’t think anyone would notice my car if I parked in the regular lot but I was being careful. I knew where there was a gap in the fence that I could easily slip through undetected, so I took a deep breath and headed for the room.
I climbed the stairs two at a time, feeling like I was drunk and had a fever at the same time. Fuck, my cock was hard. I was literally shaking I was so excited. The room in question was a room in need of repairs. There was no TV and one of the beds needed a new mattress. But there was one good bed and I wasn’t planning on watching TV. I’d sneaked a key earlier and left the door ajar for my guest. When I approached, however, the door was closed. Holy shit! Did someone come by and close it? Had I missed my chance???
I looked over the rail and there were a few cars in the lot but it wasn’t a busy night. Nobody was in any of the cars so I went back to the room and tried the key. The door swung open and a naked woman was lounging on the bed playing with her hairy pussy and moaning. I fucking felt like Superman as i slammed the door and leaned over to kiss her, sliding my tongue deep into her slut mouth.
For a woman in her 40s (my estimate at that time – I don’t really know her age), Norma was hot as fuck. She had a beautiful smile, kinky long dark hair, and tits that were more than a handful. She reminded me of a young Ann Wilson, the singer for the band Heart, before she got fat. I wanted her so bad, but then she got a funny look on her face.
She looked up at me and suddenly was embarrassed. She said, “Oh you’re younger than you sounded.” Fuck fuck fuck! Had I blown it? I stupidly said, “But I’m 18” as if that would make it better. She smiled. I’ve always looked much younger than I am. Maybe she thought I was 14 or 15 year old jailbait. I remember taking out my driver’s license to show her. LOL!
She relaxed and asked if I’d ever eaten pussy before. I said no but I was intoxicated by hers and the way she was stroking her clit. Honestly, just seeing that meant I was trying hard not to cum in my pants. She stood up and held me. I’ve always been tall so I wrapped my arms around her and leaned down to kiss her hard and deep while I felt her beautiful ass. I was grinding my cock against her soft body when she pulled away and started unbuttoning my work shirt. I felt stupid dressed as I was and was so happy she wanted me naked.
She was definitely in charge from that point on. I did whatever she said and she taught me a lot about sex. As I pulled my shirt off she leaned in and licked my chest and pinched my nipples, then she cooed her delight and pushed me onto the bed, saying something like “Let’s see that cock, honey.” I unzipped and pulled my pants, underwear, shoes and socks off in one movement. For the first time in my life, I was completely naked with a hot woman and I was so fucking into it. My cock was only average length but it was extra thick like a beer can. Over the years, I’ve gotten lots of compliments about it but none like what she said that night. She leaned over and licked my cockhead and said, “Oh my god your cock is fucking perfect baby. I love it!” Then she went down on me and I came in like 20 seconds! I was so embarrassed, but looking back on it, I think she expected it. I pumped spurt after spurt of cum down her throat as I convulsed on the bed moaning like her fucktoy. I loved it. I’d never felt so good in my entire life. I almost passed out from the joy of the feeling of her mouth on my cock and the smell of her hair and the orgasm. It was all so much to take in.
I was breathing hard when i looked down and saw her licking some of my cum off my thigh. I must have shot a gallon into her mouth. If she hadn’t been sucking me I probably would have coated the room. LOL! She swallowed every drop and kissed me. It was the second time I’d tasted my own cum. The other time was when I had tried sucking myself off and ended up dumping a load in my own mouth. This is what teens do, folks. LOL!
I loved how easygoing she was about the whole thing. She said my cum was the best tasting thing she’d ever swallowed and then she propped herself up on some pillows and said it was now my turn. She spread her legs and pushed two fingers into her sopping wet pussy then slid those fingers into my mouth. I sucked them like a cock, tasting her delicious flavor on them. She spread her pink lips for me in that hairy bush and showed me her clit, She told me to slide down between her legs and gently lick it for her. Damn, she didn’t have to tell me twice. I’d seen enough porn (not a lot but enough) to know how people ate pussy so I started licking all over her cunt. I pushed my tongue inside her and even licked her asshole a time or two while I focused on the hard clit I’d just been introduced to. God, she tasted so good. I’d heard about how pussy was supposed to stink, but hers smelled delicious. It was perfect. I loved watching her grind her hips and hold my head while I fucked her with my mouth. I’m sure I wasn’t great at it, but there’s something to be said for exploring without a map. I did everything, never staying too long in one place. When she came, she grabbed my face between her thighs and nearly tore my head off.
I was hard and throbbing again by then, so I took the chance and didn’t think twice about the cheap condoms. I moved up her sweaty body and pushed my hard cock deep into her pussy in one hard stroke. She was so fucking wet, I almost couldn’t feel it, and then she clamped down on my dick like a vice of love and I thought my head was gonna come off! I pushed into her pussy as deep as I could go, stretching her wide as I ground my hips into her. She moaned as I kissed her and I watched her eyes close tightly as she reached between us. I started to pull out but she stopped me, saying, “No, honey, I just want to play with my clit while you fuck me. Keep going baby.”
And I did. Since I’d just cum a bucketload, I was actually able to fuck her properly, pounding my cock into the heaven that was her cunt as she came again for me. I felt like a superstud even though the fact was, this enlightened woman was taking care of her own orgasms. She stroked out another one (or maybe more) before she grabbed my ass held me inside her and told me to cum. Yes ma’am! I fucking unloaded what felt like another huge torrent of hot cum into her as she licked my neck and came again. Fuuuuuck!
I honestly never felt that good again. Sex loses something when you know too much about it. It can become rote and uninspired with the same partner over and over unless you work really hard to keep things exciting. I know that now. Back then, I couldn’t believe how great it was. I actually thought I’d get better at it the more I did it. I guess I did but it was never that care free and fun again.
I fell on top of her and licked her sweaty tits as I snuggled with her. We were both worn out, but I was afraid I’d fall asleep. I had to get home before it got too late. I still lived with my parents, after all. I looked at the cheap alarm clock on the night stand. It was 12:30. We’d been playing for about 90 minutes! Holy fuck! It felt like 10 minutes to me.
She kissed me then got up to go to the bathroom. I watched her fabulous thick ass and told her how sexy she was. She grinned and sat on the toilet with the door open. These were all big awakenings for me! LOL!
She came out and started getting dressed. I just watched her. I liked being naked for her. To this day I still have a bit of a CFNM fetish. I stood up when she was dressed and she kissed me, feeling me up and stroking my cock. She complemented my dick again and sighed. I remember her saying something about not making this a habit, then she got on her knees and sucked me off again. My cock was raw but I came again for her. She licked my cum off her lips and said she should leave first so no one would see us together. That seemed to make sense to me at the time, so I kissed her and watched her go before getting dressed.
I was crawling back through the fence when I realized I had no way of contacting her. I suddenly felt like I’d lost the buried treasure I’d just unearthed and it made me a little heartsick. I went home and showered before bed, knowing I probably smelled like her perfume and her pussy. I wanted to wear that smell forever, but I had parents to look out for.
Over that summer, Norma and I met up five more times. She always called the motel and asked for me. I told everyone she was my aunt. We usually used room 218, but one time she told me her address and I fucked her at her house. That was when I realized she was married. I asked her about it and she waved it away saying it wasn’t a big deal, but it bugged me a little bit. Maybe that soured thing. I don’t know. But I never saw her again after that. But I can still smell her when I think about those nights we spent together and I’ll never forget her.
Source: reddit.com/r/gonewildstories/comments/nkyhnm/my_first_time_18m_with_a_40ishf
My man o7