Jen and Tom

Several days later, Jen was at my house, waiting when I got home. She smelled good. She looked good, her work clothes tailored, conservative, and sorely taxed to make her body look anything less than fuckable. I walked over to her, we kissed and I played in the curls of her shoulder-length hair. She seductively reached up and undid a button, and I looked down to see a hint of a lacy bra that I'd never seen before. She had learned that I was a sucker for lingerie and she evidently had made a play. My head was swimming. We put together a simple dinner, poured some lovely wine, while touching, teasing, and talking about our day.

Finally, I asked, "What's this?" drawing a finger across the texture of her bra through her top.

"I bought something special for tonight. I hope you like it."

"From what I can see, it's nice. From what I can imagine it's amazing."

"There's panties, too."

"That's part of what I'm imagining."

"Dirty old man."

We finished dinner, and retired to the sectional in the basement with our wine. Jen was putting on a show as she walked. As she took off her shoes, drawing her legs up onto the sofa.

"Undress me?" she asked, undoing her skirt in back.

I slid her skirt down, revealing the sexiest black and ecru boy short panties that let just the ripest little curve of her butt show. I ran my fingers up her thighs, then feeling the lace, warm over her pussy.

"You have more to do."

One button at a time, I worked up her top. Opening as I went. I knew it wasn't always easy for Jen to find cute, sexy, bras. She needed some support, and not everything that she thought was pretty was available, or worked in her size. But the fabric encasing her breasts was amazing. Something about fabric, tight over flesh is very arousing. I worked my way up, kissing her, cupping a breast. She stroked my eager dick through my jeans. It was still pointed down a pant leg, and she didn't have great access, but I wanted to explore and please her first.

Kissing, I was enjoying feeling and touching the edges of her lingerie, feeling the fullness and warmth of her as it filtered through the material trying to contain it.

"You are so sexy", I said, "and seeing this fabric struggling to encase you only makes it sexier." I was truly worked up. Kissing her lips, she tasted horny. "Is something up tonight?"

"I just wanted to have a special night." Jen responded. Pushing me away, her hand on my sternum, "and I want to drive tonight.

This sounded delicious. She pushed my back onto the sofa, pulled my shirt over my head. Unbuckled my belt, my jeans, and had me naked in one tug. Playfully, she climbed astride my lap, her arms a loose ring around my neck leaving some space between us. Or at least as much as her chest, hoisted into that bra, would allow. I looked her up and down as she watched.

"Doth thou likest what thou dost see?" she asked in a playful accent.

"Oh, yes, mistress."

"Well, we don't have to go that far, but I want you to know that I am driving tonight."

"Driving?"

"Driving."

"Well, you are driving me a little crazy." My fingers brushed the crotch of her panties. She slapped them away.

"See, that's what I mean. I'm in charge." brushing my fingers away.

"This could be fun."

"I hope so. Because I'm going to fuck the cum out of you."

"Er?"

"Every time before, you let me enjoy your orgasm the way I like. Tonight, I'm going to give you a good, solid fucking."

She shifted herself, brought her body close to mine and shoved her lace-covered pussy up against my rigid shaft for emphasis. I was in heaven. My girl smelled and tasted like she couldn't get enough sex fast enough tonight. Her porcelain skin was warm against me, and her bits were made the center of the show by some really sexy lingerie. Not to mention that those bits were a really, big full set of breasts and a silken vise of a pussy. Oh, and there was a lovely glass of California meritage on the end table...heaven.

She turned me sideways on the sofa, scooting down and crouching, holding my cock to her lips. She rolled her eyes up at me: what an amazing site. The valley of her cleavage hanging, held by this sexy, new bra. The sweet fair skin of her hips, curing, meeting those panties. Her green eyes looking at me as she slowly slid her lips over me. Her tongue was warm against the underside of my cock. Down. Slowly down. Not quite deep throat, but taking plenty of me in. And then teeth. Oh, how I love that. That little sharp edge of pain with the pleasure. Dragging them back up my length, up to that most sensitive point. Then suction. Her hand wrapping around both balls, squeezing as much as she thought she dared although I wanted more. But this was hers to drive. She played with me, stroking and sucking for what seemed like an eternity. As much as I wanted to reciprocate, I let it happen. She was drawing this out, letting my need build and I loved it.

She reached between the sofa cushions and came up with a condom. She had planned all of this. Torn open in a second, she rolled it the first bit on, then the rest of the way with her mouth. In an instant, she stood up, pulled her panties off in one motion, and crouched back down on me.

"This", cupping her bra, "stays on, as it seems to be having the desired effect."

"Ready?" she asked, as if my erection should give any doubt? There was something about that wry smile, though.

She grabbed the base of my shaft, pointed me toward her lips, spread herself open with her other hand, and sank all the way down me. Warmth, pressure--deliciousness. Slowly back up, then down. Grinding against me while I was deep inside her. She put her mouth over mine. She rose up, all the way, just until the head of my cock was between her outer lips. Then back down. Long, full strokes, she started to build a slow rhythm. At the end of an upstroke, she looked at me, and said "You're cumming inside me tonight." My balls churned at the thought, as she slid back down without breaking rhythm. At the bottom she whispered "But I have a secret." And back up again. She looked SO good, riding me, her thighs astride mine, her little tummy just above mine, the stark contrast of the bra as it barely contained the jiggling of those breasts, the texture in her hair as she tossed it. And back down, but there was a pause this time.

She leant forward to whisper in my ear. "I have a secret."

Pause, I just tipped my head to wait while enjoying everything that was happening.

"

Before you got home, I put a big smear of vaseline inside of my pussy. It's terrible for latex, and right now, with your cock buried inside of me it's destroying your condom. Maybe slowly, but probably not."

Jen lifted up, almost off of me. I looked down, the condom looked fine, as she slid down my whole length.

"But every stroke stresses it, coats it with more oils that destroy its strength"

Another stroke. "

The question is, will it outlast you? And if it does, will it have the strength to hold back your cum?"

Her words sunk in. Something, somewhere told me I should panic. But that's not how my body reacted. I felt myself swelling harder. I felt a wave of tingling pass through my balls as they churned out more sperm.

"Oh, I felt that. You like this game?"

She winked. Raised herself up and teased the tip of my cock with her lips. I could feel myself trying to lengthen to get back inside. She took just a bit of me in. I voluntarily flexed, pumping blood into my swollen cock. My hands found her beautiful breasts, squeezing and kneading them through the bra. This was such an unexpected turn on. She started earnestly stroking up and down on me. I felt her tighten herself for every down stroke, squeezing me, pulling the condom tighter. I rolled my head back, closing my eyes, playing with those tits.

"Carefull, those things will be even bigger if you knock me up."

Another surge through my balls, another swelling in my cock.

Jen leaned in to kiss me. Her eyes told me this was turning her on beyond what she planned. She kissed me with a need and passion I'd never felt in her previously. She took some time to grind her clit against me. I breathed a little sigh of relief, thinking this might be less stress on the condom, and give me a moment to collect my thoughts. She was getting herself close; even through the bra I could feel her breasts swell and warm with an impending orgasm. She took some slightly longer strokes, fucking herself on me, giving her clit stimulation at the bottom of every stroke. Her breath caught. Almost, not quite. She kept at it, seeking her own pleasure. Watching her, feeling her getting close was bringing me closer to the edge.

"Unhhhhhhhh" she trembled, losing a little bit of control.

Taking deeper strokes with less control and rhythm. Her pussy clamped down on me hard as she came. She kept stroking up and down, gripping hard on every down stroke. The unmistakable feel washed over me, that first wave, my body getting everything ready to cum. Jen was holding me deep inside, rocking and grinding on me, her eyes closed as she rode out her orgasm. She opened her eyes and looked at me as she felt me swell.

"Cum for me baby, cum inside me..."

I passed the point of no return. Jen kissed me and pleasure coursed from my lips, down my spine, into everything male and then that first spasm. I was cumming while we were joined for the first time. Pumping, oh--every spasm felt so incredible. Jen pulled up a little and stroked herself on me to keep the stimulation going--I shuddered two or three more spurts as my core muscles trembled. Jen collapsed on me, all warmth and softness as we breathed in unison.

After a few minutes, she looked at me with a sparkle in her eye.

"Let's see if your condom survived that."

Amazingly, I was still mostly hard as she lifted off of me. The condom covered my length, pulled tight from her stroking, the tip of it filled with milky cum. Jen reached down and cradled my latex-covered cock, giving me a gentle stroke. I shuddered, hyper-sensitive from cumming. Jen gripped a little tighter, her fascination with male orgasm combining with the visuals of my manhood swimming in cum inside the condom. She slid the rubber up just a bit, then pulled it back tight over my still mostly-hard penis.

Snap!

The latex burst, cum sprayed in all directions, and the cool air washed over my nakedness. Jen giggled.

"We were that close. One more stroke and you would have filled me"

"One more stroke and I would have know what it feels like to be naked inside of you."

"It looks like you're not entirely done."

Jen pushed the slippery, cum-covered tube of weakened latex to the base of my dick, stroking me. I was still mostly hard and I thought she was being a bit optimistic. I had, if not literally, then figuratively poured myself into her as we came, joined.

"I don't know, I'm getting softer. I might need a bit."

Jen covered my shaft with her mouth. Sucking and bobbing. It felt good. She paused, looking at me as she reached behind her and opened the clasp of her bra, pulling the straps over her shoulders as gravity took hold of her gorgeous breasts.

"Maybe a view of these will help."

She sunk back to my cock, sucking, as I hardened in her mouth. Dragging her teeth over me, cradling and squeezing my balls, then more suction, warmth, tongue, I began to harden. She sucked. Hard. Between the physical sensations, the visual, and seeing her abandon herself in getting me hard again, my cock responded. Slowly at first, then I was fully hard. I hadn't gotten hard that fast after cumming in a long time.

"Seems like now we're ready to go again." she said. "I know I am."

Another condom appeared from between the cushions. Having just cum, I knew I might take a while to reach another orgasm. But the visuals of watching Jen's hands roll the latex sheath over my hardness and the sensuality of her touch were working me up. Psychologically, knowing that only a thin layer of latex protected us, and Jen's game with the vaseline. Having just seen the last condom explode on my dick, I knew the possibility. She wanted us together naked, but wanted an element of chance. The risk was the thrill.

Jen rolled onto her back, opening herself to me. I crawled up her, tracing my fingers and then my tongue up her thighs, over her labia, up her tum across her breasts. As I kissed her, I entered her. Her flesh yielded; she was still nearly as tight as before, but her body seemed to want me inside. Slowly, I pushed in, feeling every contour and curve of her. In my mind, I wondered how long the condom would endure. Did I want it to split? I certainly wanted to feel her naked. If it split early, I could always pull out before I came. I swelled harder at the thought, as if that alone could burst what separated us.

Jen let me take her, but not without participation. Only a few thrusts in, and I felt her heels at my lower back, her hands on my hips. I broke our kiss and raised myself up to look at her; her sweet, beautiful young face. She looked up at me, not lost in her own experience as before, but locked on our togetherness. She was so gorgeous and sexy. Her neck, her collarbone, the smoothness of skin over her shoulders leading to the incredible swell of her breasts. They were firm, but as large as they were, they rolled with each thrust. This was amazing sex.

It felt as if the condom was still fine. At least it was doing enough to dull my sensations of friction against her, keeping me focused on pressure: where she squeezed me and where I pressed her.

"Just break," I thought.

I flexed my pelvic floor muscles, swelling my cock which brought a look of unexpected pleasure to Jen's face. I wanted to be as hard as I could. To fill her as much as I could. I began flexing to swell with each stroke, pausing deep inside. Offering pressure to her clit. We found a rhythm that obviously worked for both of us; breathing deepened, her legs and hands encouraging as I felt the pressure to cum slowly building inside like a dull ache.

Jen reached a plateau of need, "Just like that, Tom. Don't stop. Fuck me."

I worked to keep the rhythm, thrusting, flexing, swelling as her movements became less coordinated and headed toward spasmodic. I was getting her closer. I wanted to cum in her again, I didn't want to pull out. She opened her legs more, as if I could possibly get deeper.

"All of you, baby, give me all of you." she said breathlessly.

I felt her start to tighten around me, her legs trying to hold me but I kept thrusting. Her orgasm washed over her, I watched her bite her lip for a moment, trying to hold it off, but the fluttering contractions deep inside her were unstoppable.

"Oh, yeahhhhhhhh.....that......"

She was so sexy to watch, the need in her voice drove me over the edge and I felt the cum start to boil through all of my male bits. I thrust deep inside, and the first spurt shot into the condom. I thrust, and a wave of warmth and electricity passed over my cock as the condom burst, stretched downward by our thrusts it uncovered my cock inside of her from tip to base.

Jen's eyes shot up at me. She felt the hot liquid filling her. But we were both beyond stopping and it was too late anyway. I thrust again, and it felt like I shot even harder. Spasm after spasm, I flexed my PC muscles, swelling my cock and shooting harder, trying to push every last drop deep into her.

As the waves of our orgasms rolled back, we looked at each other. I dropped to her lips, kissing her deeply, the excitement of cupping a breast with my hand triggered one last spasm of my cock as it softened. We stayed joined for moments outside of time.

Finally, I rolled away. My cock still half-hard squeezed out of her tightness. We looked down at what was not two ruined condoms at the base of me.

"Maybe it's just me and my kinks" Jen said, "but this is arousing."

She caught both rings and pulled the remains of the condoms off of me. "

These couldn't keep us apart."

"And it had nothing to do with that dose of vaseline you snuck into your pussy."

She laughed. "Tell me that wasn't exciting. Tell me you weren't trying to burst that condom with every stroke. Tell me the tension of being kept just apart, and the danger of what might happen and when it might break didn't make that that much hotter."

She was right. She played the game well.