Annie is this tall blonde I work with who is engaged to a guy who works out of town during the week. We spend a lot of weeknights together getting coffee or a drink after work, but we never have done anything but hug one another goodnight with light pecks on the cheek. Usually we go our separate ways on weekends, but her fiance was still away for the weekend right before Thanksgiving and she asked if I wanted to go for a bike ride along the canal with her. Although I had a date Saturday night, I agreed.
I borrowed my room mate's mountain bike but I couldn't figure out what to wear because I'm not much of a biker (I play soccer). I decided to go with a pair of spandex shorts underneath a pair of hiking shorts to minimize the jostle on bumps.
When we met up at the head of the bike path, Annie was wearing very tight black cycling tights that revealed the perfect outline of her muscular legs and firm underwear-less ass. I tried not to stare and I joked that I was 'overdressed.'
'You are,' she said, and she persuaded me to wear just the spandex, putting my car keys in the little sack underneath her bicycle seat.
As much as I tried to will it away, I started getting turned on by the sense of being exposed to her. My cock swelled in my shorts and I could feel the beginnings of a boner. Luckily, we started down the canal before she noticed and as I started biking, the boner shrank down, although I could feel a wet spot of precum where the head of my cock had squeezed against the fabric.
I watched the fluid motion of her lean thighs as she pumped up and down on the pedals ahead of me. To be honest, I had to struggle to keep up at times-she is quite fit. Every so often, she looked over her shoulder and smiled at me. I was starting to wonder whether she intended to ride more than her bike...
About forty minutes later, we pulled off the path onto a narrow dirt trail towards the river. Annie continued to lead the way and I did my best to keep up over rocks, brambles and roots, but she eventually disappeared around a bend ahead of me. I followed up and nearly rode off the edge of the riverbank at a sharp turn before a big, smooth rock outcropping. Annie's bike was leaned against the rock and she was drinking from her water bottle. She looked so hot and I started to get my boner back as soon as it occurred to me how alone we were.
I got off the bike and, this time, my cock did not listen. Instead, my dick tightened up and started to bulge out against the spandex on the left side of my shorts, above the leg. I've gained a few pounds since I bought the shorts and I realized they were stretched a bit tighter than I might have wanted, riding up into my crack a little bit. Instead of being embarrassed, though, I found that the feeling of having a wedgie turned me on further.
Annie and I leaned against the rock, drinking water and talking idly when she stepped a bit closer to me and said without any pretense, 'Are you enjoying yourself? You look happy.' Her eyes were on my now-bulging cock.
I said something lame about being alone with a beautiful woman and not being able to help it. She leaned in a little closer and kissed me and asked, 'Does this help?'
'It absolutely does NOT help,' I replied, and we started making out.
As we kissed, she ground against me and I swelled up to my full length (about six inches) and thickness (about the same, in circumference). My spandex rode further into my ass and I didn't care at all and, in fact, I pulled her against me and slid my hands into her even-tighter pants. Indeed, her ass was naked in my hands and she groaned slightly as she squirmed and ground against me further. I started to pull her pants down-I was just pulling them around the curve at the top of her ass while I was pinching her hard nipples through her t-shirt-when she stopped me and suggested we get off the trail and out of sight.
We climbed up the rock and walked towards the river. It was a flat, smooth rock that had been worn down by wind and water, and we found a spot off the trail (but where we could still see the path if somebody was coming, no puns intended).
As we started making out again, Annie pulled my spandex down and freed my cock, which bounced out with a trail of precum and then stood straight up at attention. She giggled when she saw my clean-shaven balls and then said something like, 'Mmmmm, sexy...' and started gently cradling them in her hand. My cock rose higher against my stomach, wetting further.
Annie pushed me down against the rock and pulled my shorts off so I was wearing only a t-shirt, socks and running shoes. Something about the feeling of vulnerability turned me on even further and I started thrusting my cock up towards her, hoping she would take me in her mouth. She giggled again and wrapped her fingers around my shaft-to my credit (and hers) she was unable to close her hand, and she started pumping me.
'I think we should take care of you here,' she said. 'And then when we get back, I think you should take care of me.'
'Ok,' I panted. Who would have said no?
Annie started pulling my cock out and away from my stomach as she stroked me-a new move for me-and also started alternating her hands in the strokes up like she was giving me a massage. My delight was unmistakable-my cockhead was glistening with precum and droplets kept pulsing out. She stroked me, never speeding up or tightening her grip enough to trigger my orgasm, just keeping me on the edge...
I started thrusting into her hand, trying to come. She loosened her grip around me so that her fingers were tickling me, barely touching my skin. I reached down to stroke myself-I needed to cum so badly-and she gently pushed my hands away, still just tickling me, cupping my balls. What a tease!
'Please,' I begged her. 'I need to cum so badly. You turn me on so much.'
'I don't know how we're going to fit this big thing back into those tight little shorts if we can't shrink it back down somehow,' she said, tightening her grip and going back to the two-hand motion.
I groaned and fucked my hips up against her, not caring at this point what I had to do or say, babbling out a stream of lust and affection.
'Let me see if this shrinks that big cock back down,' she said, and she tightened her grip all the way, using the thumb-and-forefinger of one hand to stroke my head and upper shaft and the other hand to cup my balls and pull the base of my cock out away from my stomach.
I ground my naked ass against the rock and pumped and fucked her hands and I literally babbled out something incoherent like, 'Fuck me love you make me come and shrink, oh, shrink me!' or something like that, and then I felt the tickle rise up my shaft from my balls as a thin, almost watery jet of come burst out of my notch, blasting over Annie entirely. The next spurt was thick and long and jetted all over my stomach and the rocks. She milked me continuously as I spurted several more times, covering her slender hands with my juices. Every muscle in my body went from maximum tightness to limp as my dick kept pulsing away, dry-cumming a few more times now that I was empty. Annie rubbed my cum off her hand and against my stomach and chest and kissed me hard.
'That was HOT,' she whispered in my ear. 'And now you have plenty of time to think of what you're doing to do to me.'
I pulled my spandex on over my wet cock and stomach and followed her back over the rocks to our bikes.
I will tell you what happened when we got to her house...