My [f]riend’s sister – my [f]irst time with a woman

This is long. I’ve included the back story partly because I think the context adds to it, and partly because I just enjoyed remembering it!
I put some dashes before the sexy stuff, for those of you who just want to get turned on ;)

A few months back I sent a message to a guy from a fb group I’m in. Nothing unusual there, I struggle to have conversations in the thread style as I find it a bit overwhelming with blocks of text and lots of people (esp. strangers. Currently undergoing diagnosis for autism/ADHD/whatever the hell is going on in there…)

Anyway we got on well, he works in a book store which I think great, he’s a big non-fiction reader and knows a lot of stuff, and I’m a big leaner, I love asking questions! So we always have stuff to talk about.
One of our early conversations was on family. His sister has a PhD in theology, which I’m ashamed to say instantly led me to make assumptions about her. I’m normally really good at not being sucked in by stereotypes. I asked whether he was religious too, and he said none of his family are, his sister studies religion in the context of archaeology. E.g. comparing the fabrics used in specific periods in the Bible with tools from the weaving methods from those times found in archaeological digs (or something like that). I was instantly in awe of this woman, I’m the sort of person who asks for sources on posts all the time. But researching specifics from the Bible, this is the ultimate example of ‘source please?’

She lives about 100 miles away, in the south east of England, but coincidentally in the same city as my parents. I don’t drive so often stay with them for a week or so as public transport over that way is a bitch, so I like to make the most of it. A couple of months later I arranged a visit so I asked this guy if his sister would be interested in grabbing a coffee, as I’d love to ask her about her work. He dropped her a message asking if it was ok, then gave me her number.

A couple of days into my visit I headed to a café met up with this guy’s sister, I’ll call her Ro. Of course we hit it off, we talked non-stop. We’d only arranged a short meeting, just under an hour later I had to leave. She said since we only really talked about her work (which she was fine with!) it would be nice to meet up again towards the end of the week, so we arranged to have a drink at a place near hers. There was no attraction at this point, sure she was pretty, about 5’6″, wavy brown hair, very natural make-up. I don’t feel any attraction to people until I get to know them (literally none – I recently learnt this is ‘demiromantic’, it feels so good to know it’s a real thing and not just me being weird.) I’ve only ever felt attracted to one woman before. I get on much better with guys, so that’s where my friendships are and where relationships develop, I’ve never really had a close female friend.

The time came towards the end of the week, I finished dinner with my parents, and I headed out. I dropped her a message saying I was on my way. After arriving at the pub and some awkward scanning round from the doorway I saw Ro waving at me. She pretty much looked the same as earlier in the week. Minimal makeup, blouse with jeans, nothing fancy. The pub was pretty quiet but there were a load of tables reserved from 8pm. All the unreserved ones seem to have been long taken. It was just after 7 so we only had a little under an hour, but assumed another table would free up so we grabbed a couple of drinks and settled down. Ro had a small white wine, I just had a lemonade and lime. I don’t tend to drink much. The conversation flowed effortlessly. She asked whether I grew up nearby (I didn’t), how long my parents had lived there, how I knew her brother. Beyond that I forget. From there it was a natural progression through all sorts of subjects.

By 7:55 a table still hadn’t freed up and the ones with reserved signs on were starting to fill. We were finally asked to move at around 8:10 (we thought we’d got lucky for a moment). It was quite a long walk (or short taxi) to the next pub, so we went back to Ro’s since she lived just round the corner. We got in, I took off my jacket and shoes, and sat down on the sofa while Ro went to the kitchen. She offered me a glass of wine, and I accepted. She put some snacks on the table and we settled back down into conversation.

As time went on I found myself warming to Ro on a new level. I didn’t want the evening to end, I felt so at ease around her, we had a lot in common, and I suddenly found myself staring at her – she was gorgeous, I was mesmerized, how had I not noticed before? I’d only had two glasses of wine so it certainly wasn’t alcohol. I’ve never felt attracted to someone in less than a couple of weeks, It normally takes longer for me to break down that internal barrier. I had barely known Ro for a couple of hours. My mind started to wander – has anything about her behaviour changed to make me feel this way? Have I subconsciously been picking up on any flirting? I had no idea what to do with this. I felt a warmth and a nervous tightening through my core, but just couldn’t shift the conversation to explore it.

As 10pm approached I was gearing up to say goodbye. It was getting late and I didn’t want to overstay my welcome. I didn’t realise how late it was, it didn’t feel like I’d been round for nearly 2 hours. I was a little embarrassed, I apologised for losing track of time. Ro seemed equally shocked. We wrapped up the conversation, stood up, and hugged goodbye. As we released the embrace I felt so stupid. That would have been the perfect time to test the water. To maybe give more of a squeeze, rather than a friendly hug. I asked to use the bathroom quickly, and as I came back to the lounge Ro’s phone went off. It was a message from her brother. I said something along the lines of “Not talking about me I hope!” She laughed and said they’d not spoken for the last couple of days so he didn’t even know we were meeting up again. She suggested we send him a selfie, so I moved round next to her, put my arm round her shoulder, and we took the photo. I smiled and said thanks again for a great evening. We hugged again – I had a second chance! This time I lingered slightly, and squeezed my arms against her sides and my fingers on her back just for a second. She thanked me for asking her brother for her number and said she’d not had such a good evening for a long time. I swear I picked up on lingering eye contact and a soft smile.

Suddenly the lights dimmed to a soft glow. Ro had smart lights that were scheduled to turn down at 10pm ready for winding down to bed – ideal timing! Scrabbling for a way to use this to my advantage, I said something like ‘I’m assuming this wasn’t set up for mood lighting in case you wanted to bring me home with you after the pub’ (it wasn’t smooth…) I can’t honestly remember what she said in return as I was mentally kicking myself. It must have been something like (jokingly) ‘why, would you have come back with me?’ because I remember leaning in and saying something like ‘it depends on how much of a fun time you’d promise me’. I was grinning, it was in a very tongue-in-cheek tone but I cringed so hard ?‍♀️ Ro grinned back and softly said “Oh really?”. I respond “Well, why not”, our faces moving slowly closer together during the exchange so by that point our noses were practically touching.

*——————*

Surrounded by the dim glow of the lights, I went for it. I gently rested my forehead against hers and found her lips with a gentle kiss. We mutually parted our lips and kissed again – more confident, yet still gentle. I started to guide her back towards the sofa, our bodies pressing together while our lips found one another again and again, parting to receive the other’s, each time with more conviction. Ro took my hand and said “This way,” turning her back to me to guide me towards a door, before turning back to me, placing her hands on my hips and pulling me against her for a deep kiss, barely a gap between our bodies. She pulled me through to door to her bedroom. She unfastened my trousers while I unbuttoned her blouse. I slid the material off her shoulders and ran the backs of my fingers down her sides. Her skin was so soft.

We fell onto the bed, kissing deeply, our breathing heavy, and I felt the warmth of her stomach against mine as my t-shirt rode up. She was on top – I sat up and unbuttoned her jeans as she rolled my t-shirt up my torso. As she lifted it over my head I rolled her onto her back and pulled her trousers down. Her lines were perfect. Curvy hips tapering into a toned stomach, smoothly curving up into her C-cups. Now each in just bras and panties, I returned to her lips and thrusted my pelvis against hers. I got instantly wet as I felt my mound make contact with hers. I started to gently buck my hips and felt her inhale sharply. We instantly relaxed into it, our tongues exploring each other’s months. I needed to feel how wet she was. I gently brushed my fingers over her panties. They were wet through, though I had no idea whether it was her or me (mine were soaking). I felt her smile, and angled myself, finding her labia with my own. I gently thursted my hips. There was zero friction thanks to how wet I’d gotten. We slid against each other effortlessly, tribbing through our panties. My clit was starting to throb, I spread my legs and continued to grind against Ro, this time short and sharp, rubbing my clit against her. I needed to feel her skin against me. I crawled backwards and tore off her panties, then my own. She bit her bottom lip as she relaxed her shoulders and caught her breath. Here too, she was perfect. Her slit looked so inviting, inner labia just visible. I ran two fingers across the length of her slit. Oh god she was so wet, my fingers nearly slipped inside her by accident. I slid myself up her body and we grinded against each other again. I could have kept going like that for hours, gyrating against each other frictionlessly, skin on skin, feeling our wetness grow.

I lowered my fingers and instantly found her clit. Her legs spread open, giving my fingers access to every fold. I swept my finger tips against her in circular motions, and she started to moan. I slid my hand further down, running two fingers over her vagina, and slid my middle finger gently inside her. My hand wad soaked to the palm. I worked my finger in a circle at the base of her walls, feeling her hips buck against my hand, trying to take me deeper. I sped up, circling my finger around her, in and out. I added a second finger, this time obliging and losing my fingers in her entirely. I penetrated through her tight muscles until I couldn’t go any deeper and she rode my fingers hard. ‘Fuuuuck, oh God, oh fuck, I’m going to come!’, thrusting her hips up and down hard, fucking my fingers, soaking my hand, losing herself in the pleasure, until I felt her whole body spasm, wave after wave. I pulled out of her, my fingers circling her opening as she moaned.

Right away her fingers found me and thrust inside. I didn’t need any build-up, I was throbbing like crazy. I rolled into my back as she pumped two fingers back and forth. Then I felt a third. I threw my legs wide open, drawing my knees up to my shoulders, inviting her to go as deep as she could go. I started to gush all over her hand. There was so much power behind her wrist. She didn’t let up, her fingers kept pumping and I felt myself clench around her hand, shivers rippling down my entire body. Eventually she removed her hand, and I grabbed it, placing a fingertip against my clit. She smiled, rolled onto her side, and circled obligingly. I let the after-tremors run through me and caught my breath, finally relaxing my hips, and she drew her hand away.

We pressed our bodies against each other as we shared one final kiss. We cleaned ourselves up, I got dressed (Ro put a nightgown on) and I phoned for a taxi. When I was done our eyes met, we laughed, and she guided me back to the sofa. We talked about our plans for the coming weeks as we waited for my ride. I didn’t know when I would next be visiting, but we agreed that we would definitely meet up. And, as long as we’re not seeing anyone by then, hooking up definitely seems on the cards.

Source: reddit.com/r/gonewildstories/comments/g084oc/my_friends_sister_my_first_time_with_a_woman