My roomate [f] and I [m] part 2

Wow! First of all! Thanks for all the support and kind words. I had no idea it would be that popular. So back by popular demand. The continued adventures of Jess and I. Kinkier version. Haha

By the way I am in no way a writer so I apologize for the grammar and spelling mistakes. I will try my best to write fluently.

So a little more context to this story.
Jess and I were thick as thieves for awhile. We never talked about romantic involvement. But the sex was great and we got a long fairly well. Had similar interests. I’m a huge jock but also a nerd at heart. Star wars and football make my heart beat kind of thing. So as a job I am a licensed LMT. So I do massages.

Jess would always ask for back rubs or other little massages here and there and of course I would oblige. However this time was different. She wanted to experience a truly professional full body massage. So we set it up. I kind of always knew she wanted it to turn sexual. So I did the massage in her bed. (Which sucks) I had a massage table but she wanted the bed. *sigh*

She came in on the night of the massage. Wearing for the love of God a flannel pajama set. I just shook my head. She laid down on the bed and I began to get ready for the massage. I put on some music. We were both into 90’s rock so of course my spotify playlist went straight to Blink 182.

I slid her flannel pajama top – a paradigm of sexiness – up and revealed her porcelain bare back. I took it completely off and I worked her knots for minutes at a time – kneading, rotating in firm, circular patterns, slowly squeezing her shoulders and working my way down to the small of her back, rubbing and massaging along her spine, then down her beautiful backside, ultimately reaching her feet. She giggled alot and always pushed her ass toward me wanting me to go further. Honestly I was in professional mode and was totally focused on her. After 45 minutes she had relaxed and rolled onto her side, in the small spoon position.

Sensing the now-or-never of it all, I reached over and gently pressed my lips to the back of her neck and slid my hand swiftly up her stomach and found an eagerly erect nipple awaiting my grasp. I worked my lips on her neck, soft and wet, as my tender tweaking of her bountiful breasts was eliciting enticing moans. It wasn’t long until she rolled to her back waiting for me to do whatever I pleased.

I always light candles to set the mood. Those candles flickered off her body. She was almost glowing as she lifted her ass off the bed and she swiped her pants down and off. She was laying totally bare, contrasting wonderfully in the dim light against the brownish colored sheets.

I quickly as I could flicked off the rest of my clothes and took a moment of satisfaction in my candlelit appearance in the mirror on her wall, my gently-curved cock swelling with anticipatory delight.

I took both her wrists in my hands and pulled her arms over her head, I straddled her decisively and began sliding my cock between her, as already established amazing breasts. I had pre-cum glistening and dripping from the tip of my veiny cock. She stuck out her tongue until I slid high enough for her to lick the drip of slippery, salty fluid from my swollen head.

“mmm…” she sighed genuinely.

Knowing that the secret to keeping her interest piqued was a combination of early and often orgasms, I deliberately released her hands and slid between her legs, propping her legs on my shoulders, granting me access to her beautiful, swollen pussy. Her lips were engorged and dripping with moisture. I took a loose bit of labia and sucked it into my mouth, just building tension. I did the same on the opposite side until I plunged my pointed tongue directly into her tight, tangy pussy. She gasped in a mix of surprise and pleasure and after tongue-fucking her briefly, I slid my flattened tongue up to her quivering clit. I lapped the topside aggressively, slowing to build her climatic potential. I reached up and took a nipple in each hand and teased them, alternating with full breast grabs and massages. Her fluids began to trickle faster, and her body tensed. I kept at it methodically, persistently, only shifting between vertical and horizontal strokes of my tongue. Her whole body stiffened as she built up to cum. I steadied myself and opened my mouth wider, awaiting her treat.

Then she let go. And a torrent of salty-sweet squirt erupted from her pussy, filling my mouth so much I had to swallow and go back for more. She gushed for 4-5 seconds and writhed with pleasure as I tried to catch every drip. My dick throbbed. I loved swallowing her squirt and it got me so hard knowing how hot I got her and the physical manifestation of her satisfaction saturated my face.

She laid their paralyzed with pleasure for a few moments until she roused herself and ordered me to kneel in front of her face. All 7 inches of my cock slid deliciously into her mouth. Slowly, deliberately, carefully. She reached between her legs and swept her fingers through her moisture, then brought her finger back between my legs and teased my ass with her fingers. She knew I had thing for that after several conversations. She let my shaft spring out of her mouth and took my right ball in her mouth, sucking hard, making me tense and moan.

As soon as she took my cock back into her mouth, I knew I’d have to switch It up soon or I would send a salvo of seed straight down her throat.

“How else do you want me to please you?” I whispered.

“Just do whatever you want, I love being your sexy slut.” She said.

“Okay, you know what that means, right?” I shot back..

“I don’t care, just take me, make me do whatever you want.”….

We had talked extensively about ass play. So here was my chance. Time to go for it!

I withdrew from her succulent mouth quickly and pulled away. In one swift motion I flipped her over, onto all fours. I repositioned myself directly between her legs and I used my own feet to spread hers further apart, her cheeks starting to tease open. With one hand on each side, I spread her open and hardened further at the site of her tight balloon knot. I’d only done anything ass wise a few times. But the thought of how tightly her ass would gripped my cock, made me surge with stiffness and desire.

A drip of spit rolled down my tongue, into her crack, down to her tight hole. I followed with my probative tongue, penetrating lightly, licking intently, garnering sounds of satisfaction. I licked her a bit to invite her relaxation, and took note of just how gorgeous her ass was. With another drop of saliva deposited on her sphincter, I slowly slid in my middle finger. I felt her tightness grip me firmly and my cock jumped with expectation. With one hand occupied, I reached over to the nightstand and pulled out the bottle of lube. I squeezed a generous portion down her crack until it reached my finger – still inside her. I withdrew briefly to allow the lube to pool in her asshole and then slid both my index and middle finger back inside.”

“Here’s how this is going to go” I started “I’m going to get you relaxed and worked up. Then I’m going to trade out these fingers for my cock. I’m going to roll you on your back, and slide my thick dick inside your tight ass. You’re going to take your vibrator and rub your clit till you cum. I want to feel your ass spasm with my cock inside of it and see you squirt cum from that perfect pussy.”

“mmm hmm!” she moaned urgently. And with that I rolled her over.

After positioning her ankles on my shoulders and bending her legs back, her ass presented a perfect target. I slathered some additional lube on my shaft and pressed the tip of my dick against her puckered backside until I felt it slowly start to relax. I proceeded with caution until her tightness drew me and I was up to the hilt inside her magnificently tight ass. It was trying to squeeze the cum straight from me immediately.

I began to thrust gingerly until she acclimated and then put her pretty pink vibe to her pussy. I made shallow strokes, wanting to both draw out my pleasure and allow her second O to build. The persistent buzz complemented the fullness she felt with my cock in her ass and after a minute her tension released with a quick flash flood of cum. The sight was almost enough to blow my load but I composed and returned to my quick, shallow penetration. She began pressing her ass against me, forcing my whole shaft inside, moaning mildly with pleasure while she put the vibe to clit for one more go.

While I did my best to enjoy every tight, taboo second, she managed to build herself up one more time. After a distinct tensing and tightening, I saw a sweet little stream of cum trickle down her labia and onto my cock while her ass spasmed rhythmically. I knew that was all I could take and I told her “that’s it, I’m going to pound your ass for a second and fill you full of a huge, hot load.’

She bit her bottom lip and nodded acceptingly. I cocked back and buried myself inside her, the warm, tight depths of her ass coaxing the cum out of me with every stroke. And then it happened. A deluge of sperm shot out of me into the dark depths of her perfect ass. I convulsed 7 or 8 times until sliding out and collapsing next to her – the room just ripe with the scent of sweat, sex, and spunk.

She laid there next to me. Both is is heavily breathing. She said “You need to finish the massage….”

I laughed and laid there still shaking from probably the best orgasm I have ever had.

Source: reddit.com/r/gonewildstories/comments/bye9qe/my_roomate_f_and_i_m_part_2