This story takes place years ago. I was a sophomore in college(art student). I had always been shy, and was never very comfortable talking to women. Lucky for me, my senior year of high school, a very insistent girl asked to my girl friend and we dated until shortly before this story begins. I was newly single at that time, so on top of being shy, I had no recent practice flirting with women.
To make up for my lack of social comfort, I got a little weird. I had embraced thrift stores(velvet sport coats, torn jeans, etc.), and had shoulder length dread locks(I’m white). At odds with my fashion, I was also pretty athletic. I road a vintage road bike (which wasn’t really hip at the time) everywhere, instead of driving, I rode 40+miles per day. That and I climbed a lot at a pretty high level.
So I’m trying to say, I looked like a hippy art kid, but I was a pretty ripped little guy, and I had fairly low self esteem.
One of the art clubs I was in organized a trip to NYC for 3 days so we could visit galleries. The story begins as about 10 of us art kids jet off to the big city.
We arrived in the afternoon and went to our crappy hotel in Chelsea. However the hotel rooms worked out, I ended up in a double queen room with 4 girls… We put our stuff away and went out for food and drinks. The 5 of us in my room were all under 21 (I was 19). After dinner, the group was forced in two, the 21+ kids went out to the bars, and the 21- kids got a bottle of vodka, and after wandering around a while, went back to the hotel.
So the five us are there getting drunk, laying around in our pajamas at the hotel talking, with nothing to do. One of the girls asks me if I’m still dating Tara (my ex). I say that I’m not, and they ask if I’m dating anyone else. I say no, and the all girls sort of giggle. I’m new to drinking at the time, so my inhibitions are low. Assuming they are mocking me (per my self-esteem) I ask why they are giggling. One of the girls, the most confident one proceeds to drop truths on me that would change my life for ever.
She looked at me and said “John, you know all the girls(probably just the art girls) on campus talk about you, and all the guys hate you because it…Right?”
“You’re absolutely fucking with me” is the only reply that makes any sense. “NO, I’m not!” she responds, as the other girls all nod along like this is an obvious fact.
“The way you walk around like you’re too cool for life(thanks to my social anxiety), you look so confident…and hot.” The other girls continue to nod along.
“So all of you think I’m hot?” I ask, in perhaps the most bold and forward statement I have ever made to a group of people. “Yeah!” They all say or nod yes too”
“This is blowing my mind!” I take a drink from the bottle and I take off my shirt. Glancing over with a smirk as I scoot closer to two of the girls on my bed. Everyone laughs, but those two blush. “Your blushing! This is incredible!” I snark “You have a six pack!” one of the girls on the other bed remarks. We all laugh and the conversation rolls around, of course, to talking about sex. Jessi, one of the girls that seemed to be eyeing me the most, tells a story about how much she dislikes boyfriend. She says they are on and off, and that she hasn’t ever come during sex with him. I’m appalled and quip something about how I could help her with her lack of orgasms. She doesn’t say much, but doesn’t look disappointed in my jest.
It’s late by now, and I decide to stumble drunkenly towards this rare opportunity. “Hey! It’s really late guys, I think we should all call it night. Don’t you think?!” I say getting up and turning the main light off.
I get back into the middle of my bed, flanked by Jessi and Kate, the most attractive of the 4 girls. Jessi is petite, pale, with straight red hair. Kate is the perfect mocha brown, thin but with incredible curves, and straight black hair. I laugh at the absurdity of the situation as I turn to spoon with Jessi in the dark. My hands wrap around her and she immediately guides them up her shirt and onto her perky little tits with their tiny erect nipples. I pull her closer to me and feel her breathing harder as she feels my (frankly, pretty large) cock press agains her panties. She turns over to kiss me. The two girl in the other bed anxiously inquire in the dark what exactly we’re up to. We laugh. I kiss Jessi deeply as I feel her hand slide down my shorts and grab hold of me. I breath into her as I slide a hand down her panties, feeling her wet little pussy and sliding one finder deep inside of her. She lets out a long slow gasp. I kiss her one more time, she makes a quite moan as I slide out of her and turn over.
Kate is there and kisses me as I turn towards her. I pull her close and unclasp her bra (not sure why she had a bra on at this point) massaging her much larger breasts as she begins to breath heavily. Jessi is behind me kissing my back and neck. I kiss Kate, and slide my hand down her panties, rubbing her pussy as she breath quickens. I go to slide a finger inside of her as well, but she says stops me. I get the idea(‘no’ means ‘no’), and kiss her more as she slips a hand into my shorts as well, grabbing my now throbbing hard cock. She strokes it softly. I kiss her again and begin sucking her soft breasts. She moans quietly and pushes the covers down, so, by chance, the girls in the other bed can see everything if they happened to be looking. (Kate it turned out was a virgin) Pulling my shorts down she begins stroking my cock faster, some what clumsily, but gently. I kiss Kate again as I reach over to find Jessi’s body with my other hand.
I think Jessi became a little jealous here. She felt my hand on her breast and rolled towards me to began kissing me and rubbing my chest. Her hand passes down my chest and joins Kate’s on my cock. Kate, I think is in over her head and pulls back, happy to simply stoke my back as I turn my attention to the more willing partner.
While I’m enjoying my new found position, I’m still a little self conscious, so I try to keep a bit of low profile seeing as there are two non participants in the room.
Jessi is clearly very turned on by this whole thing. She turns over and presses her tight ass against me, while Kate caresses and kisses my back. I pull Jessi close to me, sliding her panties to the side, I rub her pussy and feel her moan quietly. She grinds back against me harder and whispers over her shoulder “fuck me please?”. Who am I to say no? I press the tip of my cock against her wet pussy and slide deep inside of her. She lets out a long, audible gasp. Still afraid to make a scene for some reason, I fuck her slowly from behind. Perhaps frustrated by my lack of gusto and more turned on than I have still ever seen another person, she pulls away, takes off her panties and gets on top of me. She begins ridding me harder, moaning louder. Kate is still here but she’s more of an observer. The girls in the other bed I think are pretending to be asleep.
I hold Kate close to me, her tits pressed against my chest as I thrust harder into her. She comes quickly once she’s on top. She asks if I’m going to come, and by some miracle, I am not. SO she dismounts, disappears under the covers and I feel the tip of my cock part her lips as she take it in her mouth….I get close to coming quickly as her tongue and lips slide up and down my shaft. My cock throbbing in her mouth I tell her quietly “I’m going to come”. As if nothing changed, she keep at it, her lips slipping further down my cock until I burst, pumping my cum into her mouth. She continues to move up and down my now cum cover shaft as if nothing happened, sucking every drop from me until I pry her off, overwhelmed by sensation….
So that was the first night anyway. When we got home, Kate and I continued to fuck regularly. Jessi seemed a little embarrassed by the whole thing, and thanks to all the witnesses, I gained an even more notorious reputation to add to my new found self-esteem. You can’t make this shit up.
Source: reddit.com/r/gonewildstories/comments/5q6oeo/mff_what_i_learned_about_myself_in_a_hotel_room