41 [M] The patient wingman and the conservative girl

My best friend Dan insisted we go to a bar so he could try and meet women. The night went well, and he struck up a conversation with a cute latin girl. And being the good wingman, I kept trying to entertain her very conservative and slightly stand-offish Asian girlfriend (Vanessa). The night went long at the bar and at 2am, my friend and the Latin girl said “hey, we’re going to go back to Dan’s house and drink some more” I was like “Cool”, but her best friend seemed put off by it.

Back at Dan’s the two new love birds made a B-line for his bedroom and before we knew it, Vanessa and I were alone in his living room. We made more awkward small talk and I got us some red wine to sip. The moaning intensified from the bedroom and it only made our situation more awkward. “I have a feeling you’re going to end up staying over, there’s a spare room, I can set you up” I had sort of given up at that point. She said “ok..show me where it is.” We walked into Dan’s spare room and I moved a few boxes he had put on the bed and made the room more presentable. Vanessa surveyed the room and as if to give approval, then said “Are you going to sleep in here with me?”. I was a bit shocked, because the way she said it was more inviting than I had expected. So I said, “If you want” and she replied “I want”… and I walked over to her, us standing next to the bed and leaned down and kissed her.

We stood there at the edge of the bed kissing, my hands running down her slender body and her hands pressing against my chest. I brushed her hair back off her neck and started to trace my tongue along her neck, my lips pulling and nibbling at her skin. Her breath was quickening and deepening, her body started to move against mine and her hands tightened around my sides. My hands slide down over the curve of her ass, and I pulled on it, bringing her even close to me. She was moaning softly now as I kissed her neck and her hand had wandered down over my bulge in my pants.

I fumbled to find the edges of her skirt and pulled it down off her hips, revealing a pair of cute, form fitting light blue cotton panties. They clung to her body perfectly and made me want her even more. My hand started to slide down the front of her panties, eager to feel the warmth between her legs and she slid her hand over mine “No… “ she said. “Sorry, I’m not a hook-up type. This isn’t normal for me. Can we just cuddle and kiss some more, I don’t even really know you”. I smiled and let out a soft snicker, and replied “Sure, let’s just calm down for a minute”. We both sat on the edge of the bed, and caught our breath. The conversation was more fluid now and I it was clear her guard was more relaxed. I made her laugh and she made me smile and we went to awkwardness to playfully getting to know each other. We kissed again and again and soon he were back to passionately kissing.

Our hands were running over each other, and this time as my hand ran between her legs she didn’t stop my instead let out an inviting moan. I ran my hand back and forth over her panties, they were soaked to the touch, much more than I would have expected from this conservative Asian girl. She was moving her hips with the motion of my hand over her panties. Her hand tightened around my wrist holding it for half a minute or more, and she suddenly pulled it away. “Fuck!” she exclaimed, “You need to stop..”

I leaned back and gave her some space for a second as she caught her breath. She had that hungry look in her eye like she was about to jump me, her body moving with each breath as she tried to calm down. Then after a few minutes of silence she said “That was not expected…That was way too fast” She paused and kept looking at me “I had a small orgasm, and it’s never that easy… sorry, it frazzled me, I’ve never came just from touching before”. I replied “I must have just hit the right spot on accident or something”. She nodded yes in silence.

Another few more minutes of her collecting herself passed, she looked up at me “I guess I owe you one.” I replied “Owe me one what?”. She smiled up at me “I owe you an orgasm silly… nothing crazy, I’m not that type of girl, but I’ll give you a hand job if you’d like?” The formality of her proposal made me giggle to myself, but I wasn’t about to turn down the offer “Sure… If you’re cool with that?” And she nodded yes eagerly.

She stood up off the edge of the bed, and pulled her top from the bar off, revealing a modest white tank top with thin straps. She was slender, with A cups and you could see she didn’t need a full bra. I looked at her standing in front of me in her blue panties and white tank top and fully apprecated how sexy she looked in that moment. “Well, you need to take your pants off” She said in a playfully sarcastic way. I stood up and undid my pants and pulled them off, she told me to leave my boxers on and I sat down on the bed again, feeling a bit awkward at how clinical this was becoming. She then dropped to her knees infront of my and assertively moved my legs after apart to slide move between them. She ran her hands over my and under my boxers, teasing my thighs with her soft hands and soon my erection grew out from under my boxers. She slid in even closer. She started to trace the shape of my cock with her finger tips. Lovingly caressing me, teasing the tip, her hand sliding along the shaft without gripping it.

It was clear this conservative girl enjoyed the feeling of touching a cock. She wasn’t timid at all. She wasn’t someone who just pulled on it until it came for her. She was adoring it, me, with her hands and massaging it gently as the sensation grew in my body. I started to moan softly as she ran her hands over me. She looked up at me, with a happy, yet evil look in her eye. One of her hands run up my thigh and under my boxers and soft finger tips slid over my balls, while her other hand continued to slide over my cock sticking out of my boxers. I leaned back to enjoy the sensation and started to moan more and more.

I could feel the sensation growing and could feel my load building inside me. She was reading my body perfectly and she pulled her hand away from my balls, and she slid even closer between my legs. She was holding my cock close to her chest, nearly against her tank top, the tip under her chin. She was staring up at my eyes, not breaking contact. The intensity of the moment building in me. My body was starting to move uncontrollably. I was thinking – she’s going to let me cum all over your chin, neck and chest… she’s not as conservative as I thought. That idea was too much for me. I exclaimed “I’m going to cum” to warn her. My half-hearted attempt at gallantry. My cock pulsed in her hands and that first gush of my seed hit her just under her chin, but instead of pulling back, she quickly turned her head down, and wrapped her mouth around the tip of my cock. She began to milk my cock into her mouth. I gasped at the unexpected feeling of the warmth of her mouth. She sucked and swallowed every drop after that first pulse and didn’t stop when I did. She kept sucking and milking with her hands, as if she had be starving for me.

She pulled away and looked up at me… This time it was me who was trying to catch my breath. I was speechless. Just looking at her, trying to wrap my head around what just happened. Then she said “oops.. I got carried away at the end, should we try getting a little sleep now?”

Source: reddit.com/r/gonewildstories/comments/8hgkyy/41_m_the_patient_wingman_and_the_conservative_girl

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