[M30/F26] – Hooked up with the woman I’ve been doing a DirtyPenPals role-play with for the last 18 months (long)

Going back to October of 2014, I started a /r/dirtypenpals RP with someone, and since then we’ve kept it going with frequent exchanges. We send messages every day or two. I recently turned 30, I’m 6’1″, and about 200lbs. I travel a ton for work, and eat out a lot, so I’m a few pounds heavy, but not bad looking. I described my character physically as a reflection of myself, but maybe in a bit better shape.

My partner’s writing was amazing, and she was creative in all the best ways. At one point she sent me a 4000 word scene describing getting herself off with a vibrator while imagining my character fucking her. It was beyond erotic, and was skirting toward, dare I say, literature. She described her character as 5’8″, blonde hair, blue eyes, and, obviously, gorgeous..

Anyways, as time went on, we started writing more out of character, usually a paragraph or two before the good stuff started up. Over that time, we definitely formed a kind of friendship, albeit one predicated on writing dirty dirty smut to each other, so sex was always an over-arching theme. My DPP partner never physically described herself, but early on did say that she was a college student, English Lit major, just about to graduate.

About a month ago, I said in a message that I was upset because I was going to have to spend Easter in Boston because of work. Because of the cost of airfare, my company made me fly in on Saturday for a Monay meeting. I sent that email on Wednesday, and got an email from her on Friday evening asking if I, “Want some company while you’re here?”

I was shocked. I had no real ulterior motives when I sent the original email, I was just venting to my friend…who I would then go on to write 1000 words of smut to. Hell, I didn’t even know she was in Boston.

I replied, “Sure, that would be great!” We exchanged cell #s and agreed to meet at a BBQ place in Davis Sq. (I was staying not far from there). She said she’s be wearing a red and black flannel shirt, and I told her I’d be wearing a hoodie with a specific NFL team on it.

I arrived at just before 6:00, and before going in seriously considered leaving. I felt like I was playing out a bizarre fantasy. She was someone I might know nothing about, (who could say if she was ever telling the truth). She could literally be anyone, she didn’t even have to be a *she*. I calmed down, and reminded myself that she was in the same boat.

I could be a total creeper, or a 600lb monster, or a convicted sex offender, or a chick. I sucked it up, and went in. I almost felt a sense of relief when I didn’t see anyone dressed in a red and black flannel shirt. I took a seat at the bar, and ordered a beer. Fifteen minutes later, I got a txt, asking if I was still coming. I responded I was already there, seated at the bar. I looked around and now saw a woman at the end of the bar with a red and black flannel shirt drapped on her bar stool. She was still looking at her phone.

My heart jumped! It was her, she was really here! We’d been sitting 10′ apart the entire time. From the distance, I could tell one thing, she was attractive! Her hair was light red, and I’d later find her natural hair color was blonde. As she looked up and we made eye contact, I froze and felt a pang in the pit of my stomach. She was gorgeous, no two ways about it. If you know who Aya Cash is, they could be sisters.

She jumped from her bar stool and hurried over to give me a big hug. She was wearing a green dress with short sleeves. She was only a few inches shorter than me, but was wearing boots with high heels. After the hug, she laughed and held out a hand, “I’m Liz”, “Hi Liz, I’m Mike!”

We had dinner, drank multiple beers and had an amazing time. She was actually 26, and she had finished a masters at Columbia in June, but stuck around to work on some research and had come back to Boston for a couple months to plan her next move. Turns out, we were both basically totally truthful with each other in our smut laden emails. During our 18 month dirty pen pal exchange, we’d both ended long term relationships, I had some health issues, she almost took a job in London, etc… By the end of the night, I was smitten with her, and she seemed to reciprocate.

It was almost 10:00pm, and we reached that odd point where either one of us makes a move or we end the night. She took out her phone, “I’m going to get an Uber, want to share it?” Like a dummy, I said, “No, I’m staying a block from the subway, I’ll just take that.” We walked outside, and she gave me a long, firm hug, then looked up and kissed me. I felt her tongue try to slip into my mouth, but she pulled away and dashed into the Uber before I could figure out how to react.

**Sexy times start here**

I got to my hotel room and jerked off thinking about her, then I felt immense disappointment in myself. If I had been my DPP character, I’d have told her to come back to my hotel and fucked her brains out (her character is somewhat of a Sub). I laid in bed on Easter morning filled with frustration. I sent her a txt, “I feel like I shouldn’t have let you get in that Uber last night.” I needed to distract myself, so I went and worked out for a half hour.

I got back to my room, and my phone buzzed with a txt from her: “no, you shouldn’t have :)” As I considered how I wanted to reply, I got another message, “I was wet when I woke up this morning, it was so bad. I got myself off in bathroom while I was at church with my family.”

As I held my manhood, reading her message, I felt my cock hard. I replied back as fast as I could with my hotel details and room #. I waited, doubt started creeping in. Was I really going to “hook up” with someone I barely knew and met through the internet? My phone buzzed again, “See you soon XO!” Yes, apparently I was.

I did a stupid dance of joy in my hotel room. I hopped in the bathroom and cleaned up, but after only a few minutes, I heard a knock on the door. I assumed it was housekeeping, because I didn’t think she could be there that fast. They knocked again, and I killed the shower, wrapped myself in a towel, and looked through peep hole. Liz was standing outside my door.

I opened it and started apologizing for not getting to the door sooner, but before I could finish she kissed me. I felt her tongue push into my mouth. My arms automatically wrapped around her, and we enjoyed a nice make out session standing in front of the door. My hands roamed over her back. She was wearing a somewhat fancy dress, having come straight from church. It was knee length, pink/salmon colored with white polka dots. Her hair was braided into a pony tail.

“I’m glad I get to see you again. I couldn’t stop thinking about you last night. I stayed up for hours re-reading our messages and envisioning you instead of your character.” She ran her hands up my torso, feeling my bare chest. I leaned in to kiss her again, and her hands slid down, causing my towel to fall off. Her hand found and wrapped around my cock, squeezing it and caressing it. I’m not super long, maybe 6.5″, but I have a lot of girth.

I stepped back and led her toward the bed. As i positioned myself, she kicked off her shoes, and crawled on top of me. I ran my hands over her bare legs, and slid them up her thighs, onto her hips until i felt the band of her underwear. and then started pushing up her skirt, until I felt the waistband of her underwear. I looped my thumbs through and pulled them off, discovering a lacy black thong.

She reached into her clutch, and pulled out a condom, but before she put it on she took me in her mouth, and started working my shaft. Her blowjob, while not the best I’ve ever had, felt awfully good. I had to stop her when I felt the first wave of an orgasm start to build. She ripped open the condom and slid it on.

She scooted forward, and lifted herself up, grabbed my cock, and then slid herself down onto me. It felt amazing. She was very tight, but then again I hadn’t been with anyone since a breakup almost a year ago, so my memory probably isn’t the best. That said, she wasted no time, and started riding me, quickly thrusting her hips forward and back.

“Tell me before you come!” I nodded back, and tried to focus on keeping my orgasm at bay.

I let our a few grunts as she started shifting her hips around, almost moving them in a circle. The woman knew how to work her hips, and after a few minutes, she had a light sheen of sweat on her forehead from her efforts. I leaned forward, kissing her, and felt her back, trying to find the zipper of her dress. I failed, and thankfully she stopped fucking me long enough to unzip the side. I pulled the dress over her, and tossed it away. She undid her bra what she leaned forward and pushed me onto my back.

Her breasts were larger than I had expected. A very full handful. Her nipples were almost the same color as her pale skin, and she had large, almost puffy nipples. The site of her oscillating breasts as she rode me was too much. I kneaded them and felt my orgasm start.

“I’m going to cum!” In our writings, her character had a thing for facials and loved cum-play, in general. She stopped fucking me, slid down, pullied off the condom and jerked me off until I started to shoot my load into her open mouth. When she kissed me I could still taste myself on her tongue, which if I’m honest was a bit odd, as my exes were all pretty anti-BJ or spit & rinse types.

We fucked once more that afternoon, then went out to dinner together, and then came back to my hotel and fucked again. Our final fuck had her bent over the arm rest of the couch as I took her from behind. I pulled her hair and was as rough as I could reasonably be and she seemed to enjoy it a lot, just like her character always did.

I wanted her to spend the night, but she’s staying with her parents and couldn’t risk pissing them off. We talked the next day while I sat at Logan and waited for my plane home. We enjoyed each other immensely, and she’s planning to come visit me at a conference in Vegas in a few weeks. There’s definitely a spark, but the distance means we won’t be starting a real relationship unless that changes. On the upside, now the erotic emails we exchange usually have attachments, and I find myself using snapchat a lot more often.

Hopefully there will be more fun tales to tell in the future.

Source: reddit.com/r/gonewildstories/comments/4g5psr/m30f26_hooked_up_with_the_woman_ive_been_doing_a