My housemate Kelly’s friend was going to stay with us for the weekend – she’d been moping for a couple of weeks after catching her (now ex-)boyfriend cheating and needed to get out of Austin so Kelly got the okay from me and invited her up. Jen arrived early on Friday and when I got home the two of them were in the kitchen with a cheesy yellow Hi-Liter pipe they’d shared in college, raiding the fridge for strawberries and grapes.
Jen was super cute – a tallish brunette with a sort of pixie cut, black rimmed glasses, like the girl next door who’s into Crossfit or something. After introductions I hid out in the extra bedroom-turned-office to give them some space and “work” (play FIFA). An hour later Kelly knocked and asked if I wanted to come out for dinner and drinks (ie would I drive so they could get drunk – this is pre-Uber).
They picked a French bistro in the hipster district and before the main course they’d already killed a bottle of wine. After dinner we wandered around for a couple of hours grabbing a drink here and there until it was decided that a bad breakup called for a new vibrator so off I drove to take two drunk girls to a porn store/sex toy shop. (Sorry, there is no threesome to come – Kelly is adamantly uninterested in dudes.) They picked out this horrifying thing for me, sort of a disembodied latex torso with breasts, a pussy, butt cheeks and hole. I declined but they bought matching beaded spinning vibrators.
They were whispering and laughing on the way out to my truck and when we climbed in Kelly looked in the back seat and said “Just do it already.” I looked back and Jen lifted up her gray sweater and flashed me – her tits were truly amazing, not large but perfectly shaped and perky with small dark areolae. “What do you think, 1-10?”
Kelly snapped me out of my reverie. “10, definitely 10.”
“I hope so, I paid enough for them…” – Jen had been flat chested through college and saved up until she could go to the best surgeon she could find for an enhancement.
Back at the house, I was dragging so I took a shower and headed for bed, leaving them to the couch and another bottle of wine. On the way to my room, Jen ran over and gave me a hug and a peck on the cheek, “thanks for the confidence boost.”
I’m a deep sleeper and when I woke up I found myself spooning Jen. She stirred when she felt me move “I hope this is okay, she snores when she’s drunk.” No problem at all, if she didn’t mind my erection pressed against her. Reading my mind, she shifted so that my cock rested between her cheeks and pulled in tighter against me. Not being entirely clueless, I picked up the hint and kissed her neck. Sliding my free hand under her tank top, she shuddered as I let my thumb graze her nipple. I knew that if this went where I was hoping I wasn’t going to last long, so I spent what felt like half an hour exploring her body, my trapped arm holding her as I teased and groped and she rubbed against me silent except for her sighs and quiet moans. Jen was bald except for a little landing strip and her panties were already soaked, as I started to gently work her clit she paused to slide them off and guided my hand, urging my fingers inside her. With my thumb still stroking her clit I was working to find the right angle for her g-spot without breaking the contact we had spooning.
“I need you inside me.”
Jen pushed me on my back and tossed the comforter aside, straddled me, beginning to slide the length of my cock along her slit. She reached down and grabbed me, and slid all the way to the base in one motion. I gasped at how tight she was and how good it felt but she was still almost silent, eyes closed, concentrating as she began to work her hips, rocking back and forth, grinding her clit against my pubic bone. I was just along for the ride, gripping her hip with one hand and cupping her breast with the other, switching, playing with her sensitive nipples.
Jen picked up speed until I felt her clench and shudder, pushing me over the edge – “I’m going to…” “Cum in me.”
And I did. I held her hips tightly keeping her in place and unloaded deep inside. She collapsed on my chest, breathing deeply as I slipped out of her. We stayed like that for a few minutes, she gave me a deep kiss before she got up and grabbed a pair of my gym shorts sitting on the dresser to run to the bathroom.
I lay there coming down from the moment and when I heard the shower running I got half dressed and went in search of orange juice. Kelly was already in the kitchen eating toast and raised an eyebrow at me.
“Was this a setup?” “No, just a happy accident.”
I wouldn’t have been mad if that was the end of it but we got one more night, which I’ll work on writing up this week.
Source: reddit.com/r/gonewildstories/comments/r3z3gy/getting_under_someone_to_help_her_get_over