This took place the year I got divorce. Her name was Jenny and she was the first person I dated after the split. Just as a heads up this tale has a lot of dialogue included. There will be three parts to this tale. Thank you for reading and I hope you have a great day.
A friend of mine had just opened a new restaurant and bar. I had started spending several evenings there each week. This got me out of the house. I needed a change after spending the initial weeks post-divorce drunk on my couch.
On Thursdays the bar side had live music. I wasn’t really in the mood but one of my roommate’s pushed the issue. I relented, if I didn’t, I’d be up there later anyway to drive him home.
The only person more social than me was my old roommate Charles. That man needed to be socialized more than most dogs. I was sitting at the bar chatting up the bartenders when Charles tapped me on the shoulder.
C: Hey, so I’m talking to this woman. You up for wingmaning?
M: Sure, I’ll cover you man.
He dragged me over to their table. I won’t say I was surprised. Charles was talking to an older Blonde. She had a friend with her that was a rather young brunette.
M: Hi, I’m…
J: I’m Jennifer.
M: Hi, Jennifer it’s nice to meet you.
This wasn’t awkward at all. I’ve been a wingman a ton over the years, but this was different. Her friend was a LOT older than her. That didn’t seem to bother Charles one bit.
M: You’re a good friend.
J: What do you mean?
M: I assume your glass is water, which means you’re the DD. That’s awesome.
J: OH, no this…I umm…I can’t drink.
M: Oh, well do you want something else?
J: Sure, I hear sprite is really in right now.
M: Was that a joke?
*She laughed*
With that the ice was broken. We had a good time chatting. She did, in fact, drink a sprite. Charles and his lady friend played the hokey pokey with the table and smoking most of the evening.
C: Hey, we want to head back to the house.
M: Do I need to drive y’all back ?
C: No, Jennifer is going to drive her and meet us.
M: Jennifer doesn’t really seem interested in doing that, Charles.
C: It’s all good man.
Well color me confused. Charles and I headed out the door and back to my place with the girls in tow. This was going to get awkward.
I pulled into my garage and we got out. The girls pulled into the driveway behind us. We escorted them in. Charles and his lady friend ran off upstairs leaving Jennifer and I alone.
M: If you want to head home you can.
J: No, I’m not leaving her here alone.
M: You know where she is, who she’s with and if you want you can have my number. Hell, take my pic. She’s safe.
J: I just don’t want to leave her.
M: I understand. I’ll be right back, do you need anything?
J: No, I’m fine.
I went upstairs and cleaned up my guest room. The sheets were clean, but I tend to dump random stuff in there. I changed into some comfy clothes and grabbed an extra t-shirt and sweats in the event Jennifer wanted to change before bed. When I got back downstairs, she was petting my dog.
M: Pup leave her alone.
My dog just sat there and smiled. She loved attention, especially from new people.
J: She’s fine. I grew up with Shepherds, she’s beautiful.
M: Don’t compliment her, her ego is big enough.
J: Well it should be.
M: Can I get you a drink or anything? Now that you aren’t driving.
J: Oh, no that’s not why I was drinking water.
M: Do you not drink?
J: No, I drink I just can’t at bars…yet.
*insert confused complex math gif here*
J: I’m only 20.
M: Oh, well in that case, offer still stands.
She got up and checked out my alcohol selection. She made a gin and tonic and sat back on my couch. My dog next to her snuggled up.
M: I made up the guest room for you and put some clothes on the bed. I hope you’ll be comfy.
J: You didn’t have to do that. I could’ve just slept on the couch.
M: Nonsense, you’ve been put out by my roommate, it’s the least I can do.
J: Would you mind keeping me company? I have trouble falling asleep in strange houses.
M: Sure.
We sat and chatted until well after midnight. I was struggling to stay awake, but Jennifer was delightful to talk too.
M: Jen, I’m sorry to cut this short but I need to get some sleep. Would you like me to show you to your room?
J: I didn’t mean to keep you up.
M: Not at all. I’ve really enjoyed talking to you. My dog has apparently enjoyed the butt scratches as well.
J: She’s such a sweetheart. I’ve really enjoyed talking to you too.
I showed her upstairs to her room and said goodnight. My dog reluctantly followed me to bed.
About an hour after we parted there was a light knock at my door.
M: Yea?
J: Did I wake you?
M: Something wrong?
J: I can’t get comfortable. Can your dog sleep with me?
M: You can try to move her, but she’s down for the count. If you want, you can have my bed and I’ll take the guest bed.
J: I couldn’t do that.
I started to get out of bed.
J: No go back to…
M: What?
J: You’re naked!
M: Oh, uh…sorry…*attempts to cover up*
J: I’ll go.
M: No, I’ll grab some shorts. You take my bed. It’s fine.
J: Just put on pants and we can share your bed. I’ll just snuggle your dog.
I put on a pair of boxers and Jen crawled into bed. Tired or not I saw her watching me like a hawk. I climbed back into bed, scratched my pup’s ears and passed back out
I woke up to Jennifer snuggled up to me and my dog on the other side of her. It felt nice. It had been quite a while since anyone, other than my dog, had snuggled up to me in bed.
I really didn’t know what to do. I didn’t want to wake her, but I also needed to get up and take out my pup. I decided to stay and just enjoy the moment. She’d wake up sooner or later and the dog wasn’t in any rush.
J: Good morning.
M: Good morning.
J: Oh…oh…sorry. I got cold last night. Your dog moved and well you were nice and warm.
M: I don’t mind, I just didn’t want you to think I was making unwanted advances.
J: No, no no, you’ve been amazing. Thank you for last night and for being understanding.
M: It’s all good.
As I finished saying good, she kissed me. Initially, I froze, but the kiss persisted. I pulled her tight against me and returned her kiss. I was aggressive, awkward, wet and all the things I think I did when I had been twenty.
Her hips began to move against my thigh as he hands searched my chest.
J: Can I touch you?
M: Can I touch you?
And with that she took off my t-shirt and sweats and I took off my boxers. Her warm naked body felt good pressed against me. Her hands finding my cock. Her hips continued to grind against my thigh.
Then she stopped and slid under the covers. Her warm wet lips found my oozing tip. She slowly took me into her mouth. First teasing my head before slowly taking me deeper into her mouth.
Her lack of experience showed, but for what she lacked in experience she made up for in enthusiasm. A whirling dervish of lust. I wasn’t going to cum like this, but I enjoyed the moment until she needed to come up for air.
I pulled her to me and kissed her. Then pushed her on her back. I began by kissing a path down her incredibly toned body. Her firm breasts distracting me, but only for a moment.
I continued to kiss her until I reached her neat landing strip and gently parted her thighs.
J: Stop. I…I’ve never had anyone go down on me before.
M: I’ll be gentle. Just relax and let me return the favor.
Timidly she gave her approval. I teased her inner thighs with kisses and nibbles. Her body began to tremble with anticipation, her pussy aching to be touched.
I settled my lips on her swollen clip and gave it a gentle kiss. Her entire body quivered. I began to slowly lick and suck her clit. She moaned and reacted with each adjustment I made.
I worked my way down her drenched slit and buried my tongue inside her. Her back arched and her hand found my head. I slowly worked back to her clit. She moaned and writhed with each passing moment.
Her breathing began to grow shorter as her orgasm began to build. Her body shook as she peaked, her cries of passion louder than her previous moans.
I kissed my way back up her body as her body trembled beneath me. Before I could kiss her, she attacked my face. The rawness taking me by surprise. She mauled me with her embrace as I began to rub my tip along her slit.
I rested it on her lips. She broke our kiss.
M: Would you like to continue, or have we gone far enough?
J: I. I want you too. Yes, I want too.
I pressed into her and stole all of the oxygen from her lungs. She gasped and tensed.
M: Try to relax, I don’t know your body. I’m going to take this slow at until you let me know you want more.
That seemed to help her relax a bit. Again, I pressed into her. She was extremely tight. I wasn’t sure if it was fitness, nerves or both. I was patient, and as gentle as I could be.
It took some time, but I eventually worked my full length in to her. I paused and kissed her. This time it was more tender, reserved and controlled.
I slowly started to work myself in and out of her. At first with slow deep strokes allowing her to adjust and relax. Her grip still tight but her wetness and comfort seeming to be increasing by the minute.
I picked up the pace thrusting into her faster now. Her breathing syncing with mine. She continued to kiss me as I filled her tight pussy.
Again, her breathing quickened. I could feel her muscles beginning to tighten around me. Her nails found the flesh of my back and her orgasm built. Her pussy squeezing me tight as her orgasm peaked. She muffled her cries of passion into my shoulder.
Once her orgasm had subsided, she told me she wanted me to cum. She wanted to make me fell as good as I’d made her feel. I cupped my hands under her ass and began to fuck her faster and deeper.
It didn’t take long at that point. It had been close to a year since I had been with anyone at that point and she was just so damn tight.
With one last stroke I pulled out and covered her stomach and breasts in months’ worth of pent up sexual frustration. Each spasm brought rope after rope of cum.
My orgasm finally subsided, and the ropes became spurts and dribbles. She lay they watching as I painted her supple canvas with my seed.
M: Wow, that was…that was great.
I leaned down and kissed her smearing my cum between or two bodies.
J: I.
M: Sorry that was a lot. I didn’t know I could cum that much.
J: That was…
M: Agreed. You want to join me for a shower or would you like some private time?
J: I, is it ok if I shower alone?
M: Sure, I’ll grab you a towel and a toothbrush.
J: OK.
She made her way to my bathroom. I checked to see if the coast was clear before grabbing her a towel and toothbrush out of my hall closet. With the shower going I knocked before entering. We all need privacy.
J: Come in
M: Towel and toothbrush.
I showed them to her and set them on the sink.
J: Thank you.
M: Not a problem.
J: Hey, before you leave. Join me?
I didn’t hesitate. She gave me the stream to wash the smeared cum off my chest. Which I greatly appreciated. Don’t get me wrong in the moment I was proud, but once the moment had passed, I was getting crunchy.
J: M?
M: Yeah?
J: That was a first for me.
M: Did you enjoy the oral?
J: Yeah, but that’s not what I meant?
M: Hooking up?
J: Well yeah but.
M: That’s not really my thing either. So, if you want to grab dinner?
J: No! What I’m trying to say is that was my, my first time.
The soap wasn’t the only thing that dropped. It felt like I’d been punched in the jaw. My head spun. I don’t remember doing it, but I apparently sat down in the shower.
Source: reddit.com/r/gonewildstories/comments/lrn52p/mf_it_feels_like_the_first_time
You dirty dawg! So smooth. ?