The one-year anniversary of this just passed recently and it got me reflecting on it. My girlfriend and I have been together for many years. Things have always been good. She gets…
The one-year anniversary of this just passed recently and it got me reflecting on it. 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. She has a sister and a brother, and while I’m just casually friendly with her brother, her sister and 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 (my girlfriend is the better looking of the two).
Spring of last year, she was getting ready to graduate college, and she was also preparing to move across the country as she had been accepted into a master’s program at another school. Good for her. I didn’t think much of it. 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 was 22 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 repulsive. We tabled the issue. I didn’t know what to say, so I didn’t say anything definitive.
Flash forward a couple months. 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 for the last 6 years at that point. 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 panicky “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.
She had a strong reaction at first, with her entire body jolting as my tongue first touched her. But then she laid back, and she was almost entirely quiet as I started to use my tongue on her. I did the same technique I did on my girlfriend, lightly focusing on her clit while my thumbs pull her hood back. But, despite her breathing picking up a little, she was not having the same reaction my girlfriend usually did. I started to stop, but when I picked my head up, she lifted her’s off the pillow and looked down at me.
“Don’t stop,” she said quietly. I immediately put my mouth back to what I was doing before. She still made hardly any noise, but her breathing got harder again, and after a few minutes I heard it. One quiet, almost whimpering moan came out of her. I looked up at her and saw she was staring down at me, so I held my gaze and kept my tongue working. She nodded down at me, and I could tell she was breathing through her nose very hard. Another tiny moan came out of her throat but was stifled by her closed mouth, but then her mouth opened as she started to breathe harder.
“I’m gonna cum,” she whispered once, and she barely got another breath in before she said it again. Then she started saying it again and again and again, at least half a dozen times before a loud moan came out of her mouth. She slapped her hand over her mouth and rolled her head down into the pillow. I felt her legs tense up and clasp around my head, and she tried to turn her hips to the side as well. I held my grip on her thighs as my tongue kept going, tongue flicking against what I thought must have been her clit through the entire thing. I finally stopped when she quit moving and went silent. When I leaned up she was staring at me, and I slowly stood up while watching her. Her expression was blank, but in an exhausted person sort of way.
“I don’t cum like that when I do it,” she finally said. She left her legs hanging open and put one finger down to her pussy, rubbing it along it to seemingly check herself. I got up and went to my bag, unzipping a pouch inside it and grabbing a condom. Her eyes went a little wide when she saw it, and she laid herself back on the bed completely flat.
“Here, come here,” I said as I opened the condom. As hot as it was going down on her, if my cock wasn’t receiving attention I could sometimes lose some of my hardness. I wasn’t limp, but I wasn’t as hard as possible. She sat up again on the bed as I got back onto it on my knees.
“You want me to?” she said, taking the condom out of my hand.
“Yeah, but first,” I flicked my thumb over her lips, “Little more?” At that she smiled again, and then she bent herself back down, bringing her mouth back to my cock. She went faster this time, sucking my cock until it was fully hard again, and I spent another few seconds just watching the motion of her face going up and down. Then I pulled her back, and she held the condom up to my cock. I could tell she had it backwards, so I took it from her and then rolled it over my cock myself. She laid back again, legs spread, and as I lowered myself down, both her hands went to my shoulders. I positioned my hips, sinking them down and grabbing my cock, and I brought the tip to her opening. I looked her in the eyes as I started to press it against her pussy, and she looked up at me, eyes almost pleading. I pushed my cock forward and felt the tip enter her. She gasped a little, but otherwise laid there.
I started to thrust into her slowly. My cock isn’t massive by any means, so I pushed all the way in and then pulled back about halfway. After a few thrusts I looked down at her and asked if that was alright. She nodded again, and I kept going. She closed her eyes and let her head fall back into the pillow, staying mostly quiet but occasionally letting out a breath that had a moan attached to it. I kept it slow and steady at first, but then as I started to stare more at her body, and watch my cock slide into her, I found myself going a little faster. She breathed a little harder at that, so I kept going. I felt bad in the moment as I thought this, but I wanted more, so I pushed myself up and pulled out. She looked up at me with a look of panic like something was wrong, but I just stayed where I was and reached down. I gripped her behind the knees and pulled her closer, lifting her legs up into the air as I put my cock back in at a downward angle. She moaned harder when I started again, and she reached back to grab her legs herself. At this point she was staring at my cock as it slid into her pussy, and I was staring down at her face, enjoying her reaction as her mouth hung open and she breathed harder. My thrusts got harder again.
She made another moan that was louder than before, and then another, and just hearing that reaction had me feeling close to cumming. A few more hard thrusts and I knew I was going to. I leaned back down, putting her hands on either side of her head, and then I rested my face in the pillow next to hers as I started to thrust harder. I heard her give a sharp moan as I started going very fast, and then I felt her arms wrap around my back.
I started to cum, hard. I’m usually silent during sex except for when I cum, and this was no exception. I started to groan out hard as I felt it happen, and as I did I felt her face brush against mine. I turned a little, and I felt her lips press against mine again. I kissed back as I reflex as I felt myself cumming into the condom. All the while I was thrusting straight down into her pussy as she kept her legs spread. When I finally stopped I felt her keep kissing me, and I kissed back a couple times before I dropped my face down into the pillow.
Everything washed away. I pulled out immediately and then got off of her. She was laying there still, watching me as I got up, pulled the condom off, and threw it in the trash. I stood at the edge of the bed and looked at her once, but said nothing. Now I was feeling bad, I was thinking that I had just cheated, this was wrong, etc. I turned and went to the bathroom. I splashed some water on my face and then wiped off my dick with a wet washcloth.
Then I saw out the corner of my eye, that she was standing in the doorway. I thought she wanted the bathroom, so I started to turn to leave, but when I moved to pass her, she put one hand on my chest again, and leaned in for a kiss. I didn’t reciprocate at first, but then she kissed me again, and her hand pushed me back. I took a step back into the bathroom, and she pushed me further until I was leaning against the sink. One of her hands was cupped, but the other went back to my dick.
At this point I was ready to tell her to stop, or to push her off me. But then as she started to jerk my cock again, she pressed her body against me, tits into my chest and her pussy grinding against my thigh. Her hand gripped my cock just the right way to jerk it when I was only half hard, and she began to kiss me harder again. The whole thing had me head swimming, but also my heart was racing, and after a few more kisses from her I turned my mouth to meet her’s, and we started to kiss harder. My refractory period was usually zero, but it required very explicit urging that my girlfriend usually didn’t bother with. In this case though, I wrapped my arms back around her as she pressed herself into me, and soon my cock was hard again. She felt it too, and no sooner had she pulled her mouth off mine to look down at my cock, did she sink onto her knees and put it back in her mouth. She went faster this time, really pushing herself down. When I saw her hands move again I realized why her hand was cupped. She had brought another condom.
As she quickly sucked my cock, she opened the second condom. She popped her lips off with a smack and then reached up, rolling it back onto me hastily. I gave it a few more pulls to make sure it was secure as she stood up. I took her by the hip and we spun around to change places, and she lifted her body up and sat on the edge of the bathroom counter. I spread her legs again and she wrapped an arm around my neck as I shoved my cock into her again.
This time it was not slow, and I had no concern for going too hard. I started to thrust into her as she breathed heavily. I reached around and put my hand on her lower back, almost pulling her in closer to me as I thrust into her again and again. Her torso tipped back and she put both hands on the mirror behind her. I leaned forward as well, and for the first time I ran my tongue over one of her nipples. It brought another tiny gasp out of her, and after a few licks I felt it harden in my mouth. I did it several more times, and then again to the other one. By that point I had to pull out and bend forward, and I ran my tongue over her pussy a few more times as well.
I was breathing heavily when I pulled her off the sink, and I moved her by the hip back into the room. She immediately went back to the bed and laid on it again, but when I got over there I spun her onto her stomach. I heard the same gasp of surprise as I did it, but she agreeably pulled herself onto all fours as I pulled her hips upward. With me standing at the edge of the bed, I shoved my cock into her again and grabbed her by the hips. I felt her wince once as I started thrusting again, but then she just started breathing and moaning like she had before.
I felt myself getting close again, so I pushed her back down. She turned around and laid back as I climbed into the bed again and then on top of her. We went back to missionary like before, only this time I told her to wrap her legs around me. She did, and the slight change of the angle on her pussy made every thrust even better. I went harder and faster, pinning her into the bed until I came again.
This time I didn’t pull out at first. We both laid there, her legs around my waist and her arms around my shoulders. I turned to face her and she leaned her head in to kiss me a few more times. This time I reciprocated, and she took both hands and put them onto my face as we kissed one more time. The last thing she said before I pulled out was “thank you.”
I pulled out, and began to clean up. I fixed my hair and cooled off my face with cold water. I flushed the second condom down the toilet, not wanting my girlfriend to know of the second round, and hid the wrapper in my bag. I wiped her handprints off the mirror with a kleenex, and came back to find her getting back into her dress. She had her panties back on as she stepped into it, and she had me zip her back up before she went to the bathroom to fix her hair and check her makeup. I got dressed again in silence. I was tucking my shirt back into my pants when she emerged again. She put on her heels, and then turned to me. Without a word at first, we locked into each other again, her grabbing my face while I grabbed her around the waist, and we kissed one final time. She said nothing else, she just turned and left the room. I tied my tie, put on my shoes, and went back to the reception.
I was greeted by my girlfriend back at the reception with a kiss on the cheek and not a single word. We didn’t speak about it the rest of the night. We even managed to have sex ourselves after the reception was done. In truth I felt a renewed vigor going into my usual sexual experience after the events earlier that night. We never had a detailed conversation about it at all. The next day she just asked how it was, but mostly with concern for her sister in her questions. I said I thought it went well, and she said her sister texted her that it was a load off her mind, and to say thanks.
A year has passed. Her sister is now across the country. She is in grad school. She has a boyfriend of a few months at this point. My girlfriend is now my fiancee as of this Spring. That’s about it. I’m not sure what else to say about the whole ordeal. At this point in my memory it just feels like any other sexual experience I had with an ex.
This is a real story guys!!! and if you wanna see the picture of my girlfriend’s sister visit my profile! and click the link!