Chapter 47

My girlfriend and I have been together for many years. Things have always been good. She gets along with my family and I get along with her's. I have always gotten along very well.

When she started college my girlfriend and I helped her moved in, took her to dinner occasionally, gave her stuff from our apartment she might need for her dorm, etc. She was nice, and I could acknowledge she was cute even though I never really paid much attention

She was getting ready to graduate college. But apparently she had been talking to my GF and was starting to get more and more nervous about the move. My GF and her sister share everything, so the conversation became frank. She was worried about moving to a place where she knew not a single person, and not only that, that she'd move there still a virgin.

That was a bombshell to me. What?! The girl at this point, and she was very cute. I had never noticed her with a boyfriend or anything, but I always just assumed she was doing...something.

Then I got the whole story from my girlfriend, which was basically that her sister had a bad experience when she was younger. A 'boyfriend' of hers at the time basically locked her in his room and tried to force himself on her, which was only stopped when his dad came home. She'd been kind of put off by / scared of men ever since.

I didn't bring it up again. It didn't seem like the kind of problem I should be involved in. But it was not even a week later when my girlfriend brought it up again, and she point blank asked me if I would have sex with her sister. I of course thought she was joking or giving me a cruel test (which was very unlike her).

So she showed me the text convo she'd been having, and the idea was that her sister needed to have sex with someone before she moved, and it would be better for her first time if it was with someone she knew and trusted.

Apparently I fit into that category. I shrugged the whole thing off. I didn't even want to think of the how of the whole thing. I didn't want to have sex with another girl in the bed I share with my gf, and I didn't want to go to her sister's shabby apartment to have sex. But in the back of my head the idea wasn't disgusting. I didn't know what to say, so I didn't say anything definitive.

We're at a family wedding on my girlfriend's side. The reception is in a hotel so my girlfriend and I are staying there. Her sister was there, and she looked particularly cute wearing a red dress that was just above her knee, heels that accentuated her petite legs, hair done nicely, etc. Despite that, I had almost forgotten what my gf asked earlier.

Then, a couple hours into the reception, when people were dancing and generally hanging out, my gf sends me a snapchat message. "Would you have sex with her tonight?"

I read it and immediately hid my phone back in my pocket for fear of someone reading that.

My gf and I went into the hall and had a very hushed conversation. She practically begged me. She said her sister was getting more and more anxious about the whole thing, she was terrified of moving at this point and just wanted this one thing off her mind.

She said we could do it right now in our hotel room, and then be done with it. I started to object again, saying this was a horrible time to do this and kind of messed up given that her entire family was around. At that point she literally folded her hands in front of her and said please. I gritted my teeth, and finally agreed.

I saw an obvious wave of relief wash over her face as I said it. She said thank you about 20 times, and then leaned in to kiss me on the cheek. Then it was right to a plan that she quickly made up. She gave her sister the keycard to our room quietly, and then sat next to me for a little while after her sister had left. We waited a few minutes, and then she nudged me to go, mouthing "thank you" again one more time, like I was going to fetch her a drink or any other kind of simple favor.

I got up and very slowly made my way back to the hotel room. The entire way there I was becoming incredibly nervous. I had only been with my girlfriend. It didn't feel like cheating exactly, but the whole thing made my nerves feel raw. I remember worrying about being able to get it up. I got back to the hotel room, used my own keycard to open the door, and walked inside.

She was waiting inside, sitting on the edge of the bed. She was still in her dress, but she'd taken her heels off. When she saw me, she stood up next to the bed, smoothing her dress but then nervously holding her hands up against her chest. I walked up, and wasn't sure what to do or even say. Finally I just point blank asked her if this was what she really wanted. She nodded without changing the expression on her face. I sighed, and there was a beat where neither of us moved.

"Do you want me to blow you first?" she asked out of nowhere. When I exclaimed a 'what?' she gave kind of a frightened "sorry sorry" and she turned away. She was beat red in the ears, and that's when I realized that she was way more nervous than I was.

At that moment I felt as bad for her as her sister must have. I came up behind her and put my hands on both her shoulders, telling her it was ok. She turned around again to face me, and she was standing right in front of me. I asked her one more time if this was what she wanted, and she nervously swallowed and nodded her head a few more times.

When I nodded as well, I moved in closer, putting my arms around her waist, just to start somewhere. She responded by going up on her toes and kissing me right on the mouth. That caught me off guard, as kissing wasn't discussed before hand. But as she held it in place, she slid her arms around me as well.

We kissed again, and then a third time as my mouth reflexively opened wider to let my tongue out to run against hers. She copied back with her own tongue licking against mine, and then she pulled back.

I thought something was wrong at first until she turned around. She pulled her hair over one shoulder to expose her back, and I realized she was showing me the zipper to her dress. I reached out and started to pull it down, and her bare back began to be exposed before she reached back up and pulled the dress off her shoulders.

The whole thing fell to the ground and she was left in nothing but a pair of blue panties. I scanned down her body as she stood there turned away from me, and then as she turned back around. She was taller than my girlfriend, and skinnier. Hips narrower and tits smaller. But overall I was surprised at how appealing I found her to be in that moment.

She leaned in again, pressing herself against me and kissing me again. I let my hands start to touch her body more, running them up her thighs and over her back before grabbing her by the ass.

She squirmed a bit at that, so I let go and put my hands on her back. We kept kissing, and then she began fumbling with my shirt, unbuttoning it in the middle without either undoing my tie or untucking my shirt. I reached up and did those myself as she undid more buttons, and soon she was sliding my shirt down off my arms. She slid both hands over my exposed chest, and I reached down to undo my belt. She looked down and saw, and then put both her hands on my pants.

It was at this point I realized that I was getting hard, and she must have too. She reached for the button on my pants, and her hands were shaking a bit. Despite that, she got my pants open, and then almost too quickly reached inside and under my boxer briefs to try to grab my cock. Her fingers touched it, and as she groped for it more I pulled my pants down entirely. My cock spilled out into her hands, and hardened even more as she stared down at it.

"Lay down," I said quietly. I was almost fully hard now, but my head was swimming. I felt more like I should be jerking off rather than having sex. She sat down on the edge of the bed again, and I took a second to fully take off my shoes, socks, and kick my pants to the side.

When I looked down at her again, she was unceremoniously sliding her panties off her legs and leaving them on the floor. I got a glance at her pussy, and she was perfectly shaved, and also looked to have a very nice pussy in general. At that moment, I didn't know what to do. I felt a bit dizzy for a second and decided to just sit down on the bed next to her. She reached over and wrapped one hand around my cock, jerking it a little as she looked over at me.

"Is this good?" she asked as she gripped my cock, pulling it up and down.

"Slow down," I said, grabbing her hand and setting the pace for her. I was always afraid of cumming too early. She continued jerking my cock up and down for a little while.

"Now do you want me to use my mouth?" she asked. Her tone was one part curious, one part desperate. I didn't say anything. I was too busy squirming at her tugging on my cock, so all I did was nod. She shifted onto her knees and then leaned down into my lap.

I couldn't see it at the angle I was sitting, but I felt it as her mouth went down on my cock. She started going up and down, and even though it was shallow, and more than once I felt her teeth more than I would like, it still felt great. I laid back on the bed with my legs dangling off it, and now I could see her sucking. Parts of her face were red either from heat or the moment, but so were her lips, and I found myself focusing on them as she quickly jerked her head up and down on my cock. Finally I had to sit up and pull her off me, because I felt that if that went on any longer I could cum from it.

"What's wrong?" she said, panting. I told her it was nothing, and that I was getting too excited. She actually grinned at that. For the first time she seemed to be having fun. I told her to lay back, and she shuffled herself back onto the bed, laying her head on the mound of the comforter with the pillow under it.

I knew I needed a break or I would cum too fast, so I got onto my knees and opened her legs. The feeling crossed my mind that this might be too much, but as I stared down at her pussy, I knew I needed to. I brought my tongue to her pussy, and started licking.