If you have any feedback on my writing or writing style please drop it in the comments. I’d like to improve my writing and I need your help to do that.
This particular memory is a slow burn.
—————————————————————————————————————————————————–
A lot of college students dream about having a super senior year. I had two, even though one was a lot of work.
By this point, digital technology had started to catch up. Digital cameras still weren’t cheap, but the quality was much better. Webcams were now up to 1.3MP and internet speeds were no longer an issue.
My last year I only had senior design classes and filler. This left me with a lot of free time in a small town. Outside of the occasional party or gameday there wasn’t a ton going on.
My digital friend had tipped me off to a new site. My first ever cam site. It was mostly forums, chat rooms and some cams.
It took me a while to find my place. Each room had different rules and personalities. I hopped, lurked and watched as a free member until I found a place to call home.
Once I was established, I built up my courage to start camming. At first just for chat, but in time putting on shows.
I built a small following, room regulars and lurkers alike. Just like the lifestyle site I was the SWM in his 20s surrounded by older more experienced people.
I made some legitimate relationships in that room. One of them led to something that has only happened once and I doubt will ever happen again.
This is the story of the first time I was paid for sex.
I’d been a member of the cam site for close to two years at this point. Most of my acquaintances were just online friends. A few of which I’d met and fooled around with on and off cam.
One of the room regulars and I had started to play privately only regularly. She was in her late 40s, divorced and a single mother.
Dawn(D) was a wonderful chatter. She had been a member and cammer on the site for much longer than I had. She ran her own room off and on but mostly room hopped. I had apparently caught her eye.
It started with the usual in chat back and forth building to her first private message. I’ll be honest, I was shocked that a woman as beautiful as her would do anything more than give me a basic compliment. I wasn’t on her digital level.
During one particular cam session her normal one- or two-line compliments became instructions. Again, I was shocked. I had planned out what I wanted to do that night. I couldn’t change, now could I?
Line after line of chat text appeared. I slowly adjusted my camera at her direction. Then my pace. *Her Cam went live*
I watched her intently. She guided my actions with her words, until I came hard for her. She followed suit not long after.
D: Would you send me a pick of the aftermath?
Me: ….Sure.
I took a moment to collect myself and then grabbed my camera. I took picks and sent them to her.
D: Mmmm…thank you.
She waved on cam and then disappeared. I cleaned up and headed back to chat. Did that just happen?
When I got up the next morning, I had a short email in my inbox with a picture attached of her soaking wet pussy. Finding comfy pants to wear to class was going to be an issue.
Over the next several weeks our play went from PM’s during my cam time to setting aside time to cam privately. We moved from the cam site to good old Yahoo Messenger. That’s where most of the cammers I knew setup email and chat accounts outside of the site.
Little by little our sessions became more intimate. She’d begun calling my name while she played for me on cam. I too had started calling hers.
Then one morning I woke up to her cell phone number in the email she’d attached a sexy picture too. I didn’t know what to do. Did I call her? Did I text her? How many days should I wait?
I waited until I talked to her that night. I didn’t want to blow it with her. Our dalliance had become almost an addiction.
M: I got your number. Did you mean to send it?
D: Yes. I was hoping to hear from you today. Did I overstep?
M: No, no not at all. I just didn’t know if you sent it to text or if you wanted me to call. I was worried I’d overstep.
D: Oh no, I wanted you to do both, either…I don’t know. I just wanted. I wanted you to know that I enjoy your company.
M: I enjoy yours too.
D: I’d like to enjoy it more.
M: I’m not sure how to do that.
D: Would you be interested in meeting?
M: Ummm…yeah but you live in Cali. I’m in school right now. I can’t afford to drive or fly there, and I don’t think you want to come here.
D: No, and I wouldn’t ask you to. What if I paid for your ticket? Would that be an issue?
M: I don’t know. I’ve never had anyone offer to do that before. Where would I stay?
D: I’d get you a hotel room. With my daughter staying with me I don’t think I could explain why you were here.
M: Ok. Can I think about it?
D: Of course. I don’t want you to feel pressured or obligated or anything. I just, would like to spend some time with you. I really enjoy our play and would like to see if it translates.
M: Ok. Talk tomorrow then?
D: Certainly.
For the first time in a longtime, we ended our chat fully clothed. It was weird and I was reeling internally. On one hand my hormones were screaming to GO, but on the other I was struggling to justify it.
She was twenty years my senior, lived across the country and I was closer to her daughter’s age than hers. I didn’t know what to do.
I called a good friend of mine and met him to talk. He was older, wiser and a lot less likely to make bad decisions than me.
I felt good getting all of it out, I hadn’t even told him about her. He knew something was up, but not that. He just figured I’d started seeing a freshman or something that he’d make fun of me for.
He encouraged me to enjoy myself and live. If I thought it was safe and that I wouldn’t be left stranded to go for it. He dropped me off later than evening and I slept on it.
The next morning, I called Dawn.
M: Good morning.
D: Its 5am here.
M: Oh shit! I’m sorry. I forgot about the time difference. Go back to bed. We can talk later.
D: It’s ok, I was already up and getting ready for work.
M: Is it a good time to talk?
D: Of course, if this about last night?
M: It is.
D: Did you decide?
M: I did.
D: Ok, so is that a yes or a no?
M: I thought I’d start by saying I’m really looking forward to meeting you.
D: *happy noises*
We talked for a while longer until D had to leave for work. The rest of the day she texted me days and flight options.
We settled on a long weekend after the holiday break. D booked the ticket and hotel room. Everything was in my name so didn’t have to worry about anything being cancelled without my knowledge. I’d take the shuttle from the airport to the hotel and we’d meet there for dinner.
The next several weeks were a mad rush of finals, the start of classes before the break and then getting prepped to leave. We talked, texted and sexted non-stop.
When the day finally arrived for me to leave, I was a wreck. I had never been that nervous in my life. What the hell was I doing? I asked myself that question from the time I got out of my truck at the airport to the time I got off the shuttle at the hotel.
Once I checked in, I made my way to my room. I unpacked and cleaned up. I wanted to be as nice as possible for that evening. D deserved the best and I was going to give her that. What the hell was I doing?
I made my way to the hotel restaurant, it was nice. It had one of those TV Chefs names on it, so it had to be good right? I asked if D had arrived as she’d made the reservation in her name and she had not.
I waited patiently until 6:30. Where was she? I sent her a text to make sure she was alright but didn’t get a response. This couldn’t have been all a scam could it?
I sat there until 7. Still no word from her. Where was she? I didn’t have the money to eat at the restaurant on my own.
I made my way to the hotel’s front desk. The person at the desk was nice enough to tell me where I could get good food in my price range.
I decided to walk, it wasn’t far, and the weather was amazing. Uber didn’t exist and it was either food or a cab and I needed to eat. As I was making my way through the parking lot, my phone rang.
M: Hello?
D: I’m sorry.
M: Where are you?
D: I panicked.
M: Where are you?
D: In my car.
M: Are you in the parking lot?
D: Yes.
M: Honk. Let me find you and we can talk.
D: Ok.
She honked a few times until I spotted her car. I slowly made my way towards sound. An then, there she was, alone in her car crying.
I froze in my tracks. What do I do? Is there anything I can do?
I was really torn. I didn’t know how to handle this situation. An yet, I started to move again.
She finally saw me as I approached the driver side of her car. Her eyes were red and swollen from sobbing. Her makeup a mess.
I motioned for her to roll down her window. After a moment’s hesitation she did.
M: Can I sit with you and talk?
D: I’m sorry.
M: You’re in no shape to drive. Can I at least sit with you and talk until you are?
I heard the door unlock. I made my way around the hood of her car. I opened the door and sat beside her.
She didn’t look at me. She didn’t really say anything. I just sat there with her for a while.
It was awkward. I was across the country, in a strange woman’s car, and she was crying. What had I gotten myself into?
Eventually she started to calm and then the words came. She was overwhelmed, I was the first person she’d connected with since her divorce. The stress, the strain and then suddenly what had been fantasy was new a reality.
She had broken. That was ok, maybe ok isn’t the correct term here, but I understood. I mostly just sat there and listened.
M: Are you hungry?
D: What?
M: Are you hungry?
D: I guess.
M: The desk told me about this taco place a few blocks away. Why don’t we head over there and eat? You’ll feel a bit better and we can talk some more.
D: Ok.
At this point I figured it couldn’t hurt to eat and talk. We were a bit overdressed, and her makeup was wrecked but it wasn’t like we were headed to a 5-star restaurant.
When we got there, I put in the order while she did her best to cleanup in the bathroom. Our food came out about the time she finished in the restroom.
She looked great. Her eyes were still red and puffy, but I could still the beautiful woman I had lusted after for so long.
We found a nice quiet spot to sit outside and as secluded as possible. I did what I could to shift the conversation away from what had triggered her breakdown. It seemed to be working.
She told me about the area, her favorite places, and what she liked to do. I responded with mine and what I was hoping to see while I was out. I was even able to keep the conversation PG, steering her away from topics I thought would create unneeded stress.
We finished dinner and headed back to the hotel. D dropped me at the door and said goodnight. I was happy she had finally seemed to have relaxed.
When I got back to my room I checked to see if I could afford changing my flight. It was doable but ramen was going to become a luxury item when I got back for a while. I decided to sleep on it, the cost would be the same in the morning anyway.
As I settled in to watch some tv and pass out my cell rang.
M: Hello.
D: Did I wake you?
M: No, just settling in.
D: Can I join you?
M: Are you sure?
D: Yes. My daughter is out tonight, and I don’t want to be alone.
M: Sure. I’ll meet you in the lobby.
We hung up and I headed down to the lobby to get her. She hugged me as I grabbed her bag. We made light small talk as we headed back to my room.
When we got back to the room D said she was going to change into her sleep stuff. I headed back to the bed. She headed into the bathroom.
I heard the door and out came the most beautiful woman I’d ever seen. It’s not like I hadn’t seen lingerie before but never like this. This woman did not shop at Frederick’s or Vicky’s. This was beyond anything I had ever seen.
D caught me gawking. There really is no other word for it but gawking. I was in awe.
D: You like it?
M: *word salad*
D: I didn’t plan for this or needing comfies. This was all I packed.
M: ….
D: I can leave if it’s an issue.
M: No, no please don’t. I just, wow, you look amazing.
She blushed and came to snuggle up with me in bed. She felt nice. She smelled nice.
I flipped around for a bit before turning the tv off. I was exhausted. The time change was finally hitting me. I was also getting hot.
Instead of freezing D out I pulled my portion of the covers down. This led to the first time my boxer short covered tent was visible. Like her “night wear” D gawked except she had the presence of mind to catch herself. I feel like that’s a superpower woman have that men will never develop.
I didn’t say anything just slipped down in bed. D settled down next to me, laying on her side facing me. She moved to get comfortable, her thigh brushing my erection more than one. The apologies shortly followed but were short lived.
We hit the lights and settled in for sleep. Sometime after midnight I woke up felling cold. D had rolled on to her side facing away from me. I adjusted the covers and spooned her.
She felt warm, soft and overall amazing. What had once been my relaxed stated started to change almost instantly. My cock hardened pressed against her warm cheeks.
I did my best not to wake her as I readjusted. My cock poking her in the butt the rest of the evening wasn’t going to make for a goodnight sleep for either of us.
I settled back in and tried to still my mind. I was not winning that battle. Her warm body felt amazing. My erection was not going anywhere…I really did need sleep.
I laid there silent. Trying not to wake her. Just breathing in her scent and continuing to lose the battle to still my mind.
Then I felt her press her ass into me. The jolt of electricity through my body was intense. I didn’t know if that was intentional, but I was hoping she’d do it again.
Again, she pressed into me. I lightly moaned. I felt her adjust, then move my hand to her breast. I gently squeezed it in my hand. Her nipple already hard.
I began tracing the outline of her hard nipple with my fingertip in rhythm with her hip movement. This elicited a low moan from her.
She rolled over to face me. I couldn’t see her, but I could feel the heat emanating from her body. We kissed, deep and passionately.
I pulled her tight as she groaned her sex against my thigh. Her warmth was overwhelming. Her taste pure joy.
The attack continued until D broke it for air. I pushed her on her back and began kissing a trail down her stomach.
I readjusted between her thighs. Not a word said. I kissed and nibbled on her inner thighs. Her goose flesh expressing her level of pleasure.
My hands slid up and I began to pull her panties down and off. I could smell her sex. I wanted her in my mouth. I needed her in my mouth.
I settled back down and again kissed and nibbled on her thighs. She squired in anticipation for what was to come. My tongue teasing her smooth lips.
Her breath became short with each passing moment. I teased her one last time before sucking her swollen clit in to my mouth.
Her body reacted immediately. Her breath grown, her back arched and her thighs tight around my head. I released the suction and began to lick, nibble and suck her clit.
Her moans came back with her breath. Her hands found my shaved head. Her nails a sharp reminder of the line between ecstasy and pain.
I slowly worked my way down her swollen lips. Nibbling on them as I did. She seemed to really enjoy that. Before penetrating her with my tongue.
She pulled my face in with her hands and ground against me as I tongued her as deep as I could. My face now covered in her juices. She worked my face in rhythm with my tongue.
I teased her to the edge as best I could before dragging my tongue back to her clit. Her frustration getting the better of her as I did. Her nails again sharp against my scalp.
Again, I sucked her clit in to my mouth. She ground against me. I worked her love button and she fucked my face. I could feel her orgasm building.
Her body tightened, her breath quickened, her moans becoming louder and louder. Her release was painful. Her thighs too tight, her nails drawing blood, but her ecstasy drowning all of that out.
It took her time to comeback to earth. Her mind spinning. I let her settle, her sensitivity was off the charts.
D: Mmm…thank you. I…that’s the first orgasm from another person I’ve had in years.
M: I’m glad I could help. Would you like more?
D: Yes please.
This time I didn’t start with her clit. Instead, I started by cleaning her cum form her lips. I stopped as I approached her bottom. We’d talked and roleplayed analingus, but she’d never experienced it and was nervous.
I went for it. I continued cleaning her up until my tongue reached her puckered asshole. This startled her but she quickly relaxed as I gently tongued her.
The moans started shortly after. Her body now starting to relax more.
D: That’s nice. Please keep doing that.
I continued and soon her hips had joined me. I adjusted from a gently like to tongue fucking her ass. He seemed to like that the best as we worked as best, she could meet me.
At some point her hands found my ears. She pulled me up her body and kissed me. My erection pressing against her wet lips.
She cleaned my face with her tongue between kisses. I didn’t blame her, she tasted divine.
D: Roll over! It’s my turn to take charge,
M: Yes ma’am!
I could feel her glare as I moved to my back. She straddled me. Her wet lips teasing my erection.
D: I have been lusting over this moment for months. I can’t believe it is finally happening.
I felt her weight shift and then my tip pressing slowly into her. Her breathing again slowed and she slid down my shaft inch by inch. I wasn’t worried about my size being an issue, she’d teased me with larger objects on cam.
When she reached my based, she settled and slowly exhaled.
D: Damn, I’ve missed this SO much. You feel amazing.
M: You feel amazing too.
She leaned down and kissed me. I held her there as she began to slowly work her hips. I was in heaven. Her grip felt amazing, and her kiss was intoxicating.
She broke the kiss and sat up again. She found a nice pace and began to work my shaft in and out of her. My hands found her breast, thumbs teasing her now exposed nipples.
I could feel her beginning to tighten around me. Her pace shortening as she began to grind against me.
She grew quiet again as her body tightened. Her orgasm came as a rush of sound, movement and fluid. She wasn’t a squirter, but she covered me in her cum. Her moans loud enough the desk called in the morning.
She collapsed against me. A sweaty mess, breathing hard. I adjusted my legs to slowly work myself in and out of her. She didn’t protest.
Slowly she began kissing me again. Her body lay against me as I worked my length deep into her.
D: Can you cum like this?
M: It might take a bit, but I should be able to.
D: Cum for me. I need that.
I adjusted as best I could. D didn’t want me to hammer her she wanted it slow and deep. I did my best to oblige while she did her best to squeeze every inch of me.
It took me some time to find the right pace and angle but once I did it wasn’t long. My orgasm built thrust by thrust. D knew it was near and kissed me passionately.
I gripped her hips and thrust deep into her as I reached climax. My orgasm sounds lost in our kiss. My eyes filled with stars. It truly was a memorable moment in my sexual history.
D held me close as I came down. My cock still inside of her as he gently kissed me.
The rest of our weekend was spent mostly in my room. I didn’t get much site seeing done on that trip. Just lots of room service.
When I got home, I found a package mixed in with my clothing. I didn’t remember putting anything in there. When I opened it, there was a handwritten letter from D and cash.
I’d like to say we stayed in contact. We did for a while, but the money made it awkward for me. Maybe I just needed to mature, but D met someone and that as they say, was that.
Source: reddit.com/r/gonewildstories/comments/lgapse/mf_paid_in_full
Great story!
Since you asked for feedback- I started to read but saw how long it was then stopped reading? Might just be me but balancing details and length are important. Super short no details posts aren’t great- so not saying do that either!