This tale has been in the making for months. Tina is one of the first women to message us on reddit, saying she had been a lurker for years but that my stories prompted her to finally find a valid user name and message us. She described herself as 23 years old, 5’6 and 130 pounds, curly black hair, tan skin, and brown eyes, but this gave us only a vague idea of how attractive she is– she’s a stunner. She also discussed some of the hobbies we have in common and various other personal details that really endeared her to us. We started talking way back in October, but between Friendsgiving, Halloween, and various travel plans, it was difficult to plan a date together. We moved from reddit to text and snapchat occasionally swapping pictures, but nothing too explicit. Then, the day of our big date– nearly a month after we started talking– she told us that she had started casually seeing someone and she wouldn’t feel comfortable being intimate with us. It was somewhat disappointing, but we took it in stride and told her that it wasn’t a big deal and that she should keep us in mind in the future.
A couple months passed and I figured I’d text her again to say hi and see if anything had changed. It turned out to be the right move– she said we had been on her mind and that she’d been trying to work up the nerve to reach back out to us. She was out of the country at the time, but when she got back, we planned a date for the following weekend. There was a bit of sexting and some more snapchatting, and everyone seemed very excited. The night finally came and we got to the restaurant. Fun side note– we ran into a couple friends at the same restaurant who don’t know quite how sexually deviant we are, and kinda had to snub them and sat on the other side of the place. We didn’t want Tina to think that we had invited her to a group date or something weird!!
In any case, we said hi to them and started heading to our table when we promptly ran into our date. She looked great, by the way. She had on this little black dress with strappy things in the middle that showed off her chest, and a pair of stockings on her legs that made both Rachel and I widen our eyes in appreciation when she got up to go to the bathroom and we got a better look. So we hugged and sat down, and the tension in the air was immediately apparent. We had known her for the longest out of any of the girls with whom we had met, and here we finally were! I think we were all a little nervous, but luckily, we were at a rum bar and promptly ordered some mojitos to lubricate the situation. We talked about her vacation, ours coming up, hiking, our jobs, etc… we eventually moved onto the subject of sex. One thing that stood out and got us very excited was when she told us how easy it was to get her off. As someone whose favorite thing about sex is the woman’s (or women’s) pleasure, this was lovely news. She had told us in her initial messages that she had never been with a girl before, and that she had only had some experience with bdsm, but she was interesting in exploring both further. She outright told us she was really nervous at this point, but we told her the truth– that nothing had to happen, and if anything does, we can take it very slowly, one at a step at a time, and we were both very into enthusiastic consent. Most importantly, we told her that we were being genuine when we said in our posts that we’re not *just* looking for a girl to bang. We’re looking for a fun person with whom we can spend time… who is also looking to have fun in bed. This put her at ease a bit, and when I suggested we go back to my house for a few more drinks, she accepted. She later told us that she had planned on refusing my inevitable offer, but that when I asked, she surprised herself by saying yes. Lucky us…
I share a house with three friends that I’ve known since college and who are generally aware that my girlfriend and I see girls occasionally, so they didn’t ask too many questions when we went to hang out in the living room for a while and finish a couple bottles of wine. Initially, I was sitting next to Tina on the couch and Rachel was sitting in front of us on the floor. We talked for at least an hour, maybe two, and at one point, Tina decided that she’d be comfortable with not doing anything that night, but if she changed her mind, she’d make a move. Well, obviously, since I’m telling this story here, things eventually escalated. She seemed to open up quite a bit and get a lot more comfortable thanks to the wine and fun conversation. Over the course of our talking, we discussed her piercings (nose and ears) and my tattoos, so I took off the henley that I had on to reveal just a wifebeater underneath. My hand would occasionally brush her leg, and ended up resting there. She began stroking my hand and invited Rachel up onto the couch with us. We sat like that, with Tina in the middle, for little while, and I’m sure it looked funny to my roommate when things were heating up and we abruptly paused our conversation while he came downstairs and muttered something about getting his charger and some weed. We giggled as soon as he left, hands wandering around each other in a rather PG way for the time being. I remember Rachel commenting on how amazing Tina’s stockings were, pulling up the bottom of her dress a bit and exposing the lacy tops. I forgot exactly what was said, but there was a lull in conversation, and while Tina was looking at Rachel, I put my hand on her cheek and turned her face towards mine.
We locked eyes for a moment and I leaned in for a kiss. Chaste, at first, but we began using our tongues and when it finally broke off, she looked pleased. She turned, somewhat hesitantly, towards Rachel, and they kissed. I was trying to be careful not to escalate things too fast, but I was dying to let my hands explore her body. While they made out, I kissed her neck and her ear to some delightful moans, my hands stroking her arms and legs and stomach. After a few long moments, she pulled away, “I’d never kissed a girl before.” Rachel smiled and replied, “I’m happy to be your first.” At that moment, we heard a voice at the top of the stairs, and it startled us. I suggested we go to my room, and both girls agreed. I put my longsleeve back on– only out of decency; my housemates clearly knew what was happening– and we got our wine and went upstairs. I quickly put on some music and we began kissing each other in earnest.
Rachel and Tina were kissing with the latter’s back to my bed, so I sat behind her and felt her up and pressed my growing erection into her backside– a fantasy she had voiced specifically in our sexting. A few times she fell back onto me, but I didn’t mind in the least, as I was busy stroking her over her panties and squeezing her breasts through her top. She began pulling Rachel’s cardigan and blouse down to expose her breasts, so Rachel stepped back and took off her top, then her bra. I don’t really have a visual recollection of that, so I must have been busy kissing Tina from behind with a hand on her throat and occasionally a fistful of her hair. She then took off her dress, leaving her in just her panties and stockings (incidentally, I learned what pasties were that night). I hastily followed suit, pulling off my henley and forgetting that my tank top was tucked into my jeans, so I ended up ripping it a little when I got shirtless. They collapsed on the bed kissing each other, and I was marveling at the gorgeous sight of two beautiful ladies making out in my bed– a first for me, as all of our other adventures have taken place at Rachel’s. I let my hands feel every inch of both of them, and Rachel and I quickly discovered just how sensitive Tina is. They were kissing, and I believe it was while I had my tongue in her ear and each of us had a hand tweaking her nipples that she had her first orgasm of the night. So… like, *really* sensitive. She scrunched her face and made these adorable moans, but we didn’t stop there. She was resting on her back, catching her breath, when I began pulling her panties down and kissing around her inner thighs. I insisted she keep the stockings on (I may have a thing for stockings now btw) as I nibbled her soft skin and teased her most private area. I began kissing and licking her already wet lips, tasting her and burying my tongue deep inside of her after making out with her slit for a while. Her clit was super hard and very easy to focus on, so I trained my mouth on that while my fingers began pushing inside of her. Her moans began getting deeper, almost guttural, as I started stroking her g spot in a come hither motion. I held her hips tight with my free arm and kept at it while Rachel continued kissing her and playing with her breasts. I got a wonderful prize for my efforts– she squirted down my chin and my forearm in a rather convulsive climax that I did my best to keep her still throughout.
(continued in comments…)
Source: reddit.com/r/gonewildstories/comments/7vfous/patience_with_a_firsttimer_pays_off_huge
(Part 2)
She pulled me away when she got too sensitive, slightly embarrassed at the wet spot she had made on my sheets. We both reassured her, Rachel insisting (accurately) that that was exactly what I wanted to happen. At this point, I crawled up her body and we kissed, me telling her how amazing she tasted and her glowing and stroking my cock a little. She traced my tip along her pussy and rubbed it on her clit as I looked her in the eyes. We all had clean bills of health from the doctor (which we brought to the restaurant to exchange), but eventually thought it best for me to put on a condom nonetheless. I gladly did and positioned myself on top of her, with one leg on my shoulder. I was getting really deep like this, so I decided to do the same with her other leg, while Rachel was looking on and stroking both Tina and herself (I’m pretty sure she got herself off at least once or twice while we fucked). However, in this position, I was getting too deep for her comfort, so I set her legs back down and continued thrusting into her and elicited some amazing sounding moans. Apparently I was in a pleasure-induced delirium, because Rachel told me afterwards that Tina was talking about how big I felt and how deep I was getting, but I have no recollection of that. Said pleasure (not to mention wine) made things a little hazy, but I think I came first and continue fucking her anyway until she came as well. I loved the way she was grabbing my ass and stroking my face and head until I collapsed on top of her and rested there for a brief respite.
At this point, I got up to take the condom off, and by the time I got back, the two girls were laying down next to each other and kissing once again. Reticent though I was to intrude on such a delightful sight, I got between Rachel’s legs and did what I love most about sex: eating pussy. I licked up her incredible wetness and focused on her clit for a while, pursing my lips around it and flicking my tongue against it. I slipped my fingers in and worked her g spot slowly at first, but relentlessly, and until I felt her pussy muscles squeeze my fingers and she came on all over them. I had Tina taste them before kissing her deeply and moaning into her mouth. She then mounted Rachel and was straddling her leg and making out with her, her lovely ass sticking up in the air, right above those darling stockings. I spanked her a few times and teased her asshole with a wet finger to gauge her interest. She seemed receptive, so began licking up along her slit to her asshole while I fingered her. Again, I hammered her g spot until she came again, gushing onto my forearm. I pulled back to get better leverage with my fingers and I remember watching her drip onto my mattress again and again. I collected it in my free palm and slapped her ass with a wet hand before cleaning it off with my mouth.
She fell onto Rachel at this point, who I believe fingered herself to another orgasm at this point (I think Tina was trying, but I distracted her big time) and we all laid there for a moment, catching our breath and joking around a little bit, “Are you still nervous, Tina?” We took turns going into the bathroom, and I remember laying next to her on the bed and her commenting, “You have some magic fingers,” to which I just laughed and gestured to the acoustic hanging on my wall. “It’s the guitar practice.”
We all cuddled for a while until Rachel and I began kissing and I got hard again. I wasted little time in positioning myself between her legs and fucking her for what felt like several orgasms for the both of us. I was kissing Rachel and Tina off and on, watching them kiss each other, and generally just amazed at how I was still hard after cumming so many times. We fucked until I legit couldn’t hold myself up anymore. (Shout out to yoga for keeping me up that long to begin with.) We took another rest and I very distinctly remember lying on my back with Tina’s head on my chest and Rachel spooning with her. The music was still playing at this point and the light was on, but I couldn’t possibly wake either of them up by standing up, right? I managed to reach the remote on the headboard of the bed and lower the volume incrementally until it was just above a whisper, then turned it off entirely. I was just barely in reach of the neck of my nightstand, the only light in the room, and I managed to turn it off quietly, placing it down softly as a shit-eating grin of satisfaction spread over my face. We fell asleep like that, adjusting a few times and getting up once to finally take those stockings off.
We fell asleep once more, Tina in the middle.
I don’t remember who started it, but it’s very on-brand for me to wake up with my fingers between someone’s legs and my erection poking their hips. I suppose I woke her up, which woke me up, and we started all over again. We kissed and I rubbed her clit gently until she came, by which point Rachel was up and kissing Tina and playing with her nipples. For a while, she was jerking me off and I was very close to cumming on her flat, tanned stomach, but she asked me to get another condom on, so I could hardly complain. This time felt a lot more passionate, with me on top of her and wrapping my arms her as I kissed her lips and her neck and her ear, listening to her whisper how incredible my dick felt until I came again. After resting for a little, I stood up to dispose of them condom once again. When I got back to bed, Tina had her head between my girlfriend’s thighs. The lights were still out, so I couldn’t see exactly what she was doing, but it looked like she had a hand there, too. Whatever she did, it worked, because I was only kissing Rachel for a few minutes before she whispered the she was going to cum, and then shivered as she is wont to do during a climax. Tina kept going, though, and I was getting a little envious until Rachel asked if I wanted a turn. Well *obviously* I did, so I went down on her for another orgasm, but by the time I pulled away, she was still ravenous. She plunged her hand between her legs and worked it there furiously until she came for what was probably the hundredth time that night. I got some water for us all and we returned to our peaceful slumber, Tina in the middle once again. She had to wake up a few hours later, sadly, so we couldn’t all wake up together. Rachel kissed her goodnight and then I walked her downstairs and did the same, agreeing that we would need to see each other again soon.
Sounds like a great time was had by all!