My whole life, I've always had lots of typical 'male' fantasies. But a few years ago, I started having a recurring fantasy about a woman taking me with a strap-on. I would be laying on my back, legs up and spread... with her between my legs. Pretty much a reverse missionary position. I couldn't imagine doing this with another man. But with a woman, Ahhhh... amazingly erotic!! For me, the extreme closeness during sex... being linked *deep inside* a woman... that has always been an important part of sex. And now, I just wanted the experience from the other side. Casual discussions with my wife pretty much ruled out living the fantasy at home. But having just turned 50, I decided it was time... something I really needed to do. So I took an ad with an online service describing my fantasy and asked for any interested women to contact me. I had an immediate reply, but she wanted her husband to be there to watch. I lied and told her I had already found a partner. I then waited four weeks with no activity before receiving THREE replies over one weekend. I eliminated one because she was in her early 20's (too young). Another was scratched because I'm pretty sure she(?) was in some stage of gender shifting. But the third respondee was Anne... my age, lived about 60 miles away, had strap-on experience and requested discretion. She was perfect! We swapped a few emails, talked on the phone three times and finally agreed to a mid-week afternoon triste at a motel half way between our homes. After making contact with Anne, I began to question if I was really ready for anal penetration?? It had been 30 years since I last had such sexual play. So, I bought a vibrator and had three private sessions. I had selected a small vibrator... I wanted penetration, but had no desire to see what my capacity might be. Even with the small dildo, it was not immediately comfortable or fun. But I learned to relax and was able to fully insert the vibrator while masturbating. In the past, Anne had regularly enjoyed using a strap-on with her husband. But, they stopped the practice a year ago... and now Anne was keen to sample it again. During our talks, we agreed that satisfying my fantasy was to be the extent of our meeting and we wouldn't enjoy any other form of sex together. Finally our day arrived and we met in the motel room without a hitch. We took our time, relaxed, sipped wine, chatted and enjoyed having actually met. We gave each other a foot massage (having found that to be a common interest) and Anne suggested taking a hot shower. We went together into the bathroom, but only I stepped into the tub. Anne stripped down to sexy bra and panties... lacy nothings. Because of all the focus on *my* fantasy, it was first now that I noticed how sexy she was! She was almost as tall as me, maybe a bit too heavy with smallish breasts. But her pretty face and devilish smile completed an ideal partner. She washed my back, chest and stomach with her hands... and dipped lower to do a soapy massage between my legs. Finally, one hand walked across my buns and slipped between my cheeks, while her other hand pressed onto my back. I bent at the waist and leaned into the warm splash of water, hands against the wall to steady myself. Anne provided a leangthy, sudsy teasing before slipping a finger past my rim. Although we had been enjoying steady chatting, we now fell silent while Anne used her fingers to delicately relax and open me. Once out of the shower, I was aware that we now had 'purpose' and we began working to set the stage. It was here that we noticed the one problem with our plan. I had brought along my vibrator, which was advertised as fitting the harness that Anne brought along. But it just wasn't a match.. which left us to use the large dildo that came with Anne's harness. It was only an inch or two longer than my *tiny* vibrator, but it was twice as big around. I held the huge cock in my hands and slid my fingers along its length. It was softer than my vibrator... a jelly dong, flexible and more life-like. I laughed at the thought of having that go in me, but Anne was very reassuring that it was going to be fine. 'Trust me', she said with that suspicious smile as she fitted the harness. I watched as she tightened straps... a bit disappointed that it wasn't *up*... not an erection, but swayed side-to-side below... a clapper in a bell. It took a bit of shuffling to get the right position. I sat on the couch and scootched down so that my lower back was on the seat. Anne used the other cussion from the couch and a pillow as a platform for her to kneel on... getting to a comfortable height. She unsnapped and dropped her bra... which we had discussed as being part of my fantasy. Gravity worked on her tits... dropping them into heavy rounded bottoms. Anne knelt close in front of me, using a creamy oil to lubricate the dildo... stroking it as if to make it even larger. Finally, she leaned in between my legs, holding the shaft of the dildo... and directed it to its target. I stared at the device as it neared... and jumped when I felt its touch. There was no entry, even though I felt it press direct on my sphincter. Anne began a continuous cooing discourse telling me to relax and how wonderful this was going to be. I closed my eyes and reached down to feel the joining. Anne rubbed the cock head into me and squirted more lube. I heard her voice rise to an expectation... and then go quiet. I exhaled and relaxed. A second later I felt the head of the dildo slip past the rim.... and poke into me. Open-eyed and gasping, I grabbed hold of the shaft to stop its entry. *Ouch* Anne restarted her soft vocal encouragement and began massaging the insides of my thighs. I slowly rocked side-to-side, letting things settle to a fit before letting go of the shaft. I began to answer Anne's cooing and placed my hands on her hips, feeling her lean forward again. Slowly, the huge shaft slid in deeper... one inch... this was uncomfortable, but not painful like the initial penetration. Two inches... I felt SO full... and I began puffing, shallow breaths. Anne paused... and pulled back a bit. She lifted my legs more and began an in-out sway... slow tiny movements.. each motion pushing in a tiny bit more before pulling out. She made a longer thrust... inserting another inch (?)... and then repeated the sway before again penetrating deeper. This was a slow process... how much time it took I do not know... 5 mintues???.. 10 minutes??? But she finally leaned heavily on me and lowered herself slowly. The dildo slipped fully in and I felt Anne's hips press into my cheeks... Ohhhh..mmmmmmm... complete penetration. *This* was what I wanted. Two people coupled so that they could be no closer. I reached behind her... pulling her even tighter and lifted my hips to ensure we were fully joined. I now realized how much Anne enjoyed this... her eyes closed... maintaining pressure, slowly rotating her hips... with small gasps and quiet moans interjected into her breathing. I found that my hand was on my own cock... but was surprised to find that I wasn't fully erect. I was heavily engorged, but not stiff and upright. Why??? Anne finally whispered a quiet 'Yesssss', exhaled deeply and giggled. We exchanged smiles as our eyes met and she leaned away... pulling half of the cock out of me. This sensation was ENORMOUS... as if I was relieving myself. But before I could say anything, Anne reversed the motion and again slid the dildo fully into me. This was quicker and forced air from my lungs with an vocal 'uuuhhh'. She pulled back again and repeated the thrust. For some reason, I hadn't expected this. My fantasy was to feel the full coupeling from a woman's view, but Anne was now actually *fucking* me! She repeated the motions... increasing the speed of each thrust... forcing the shaft into me harder each time. My cock stiffened... erect and throbbing... lifting and pumping in unison to Anne's entries... each thrust filling my hardness with blood, forcing it ever larger. I needed to pop my load, *NOW*, but it wasn't happening... and Anne continued to enjoy our sex using a hand to stroke my shaft with each plunge... dozens of thrusts... stretching me for minutes... punishing me... repeatedly forcing the dildo into me... until my heavy load was finally spewed onto my own stomach. This signaled an end for Anne... stopping her thrusts and we slowly pulled apart. I was amazed watching the huge cock emerge out of me!! We talked about what happened and both agreed that it was something special. She asked about repeating doggy style, but I declined... I wasn't even sure if I'd be able to drive home as it was! So how was it?? It was GREAT... waaaay more than what I expected. It was also my only meet with someone from online, proving to myself that it can actually happen. Would I do it again? Well, I still have Anne's phone number...