Switchplay

Hello, I'm Anne and I'd like to tell a "tail-tale" of my own. I had to think carefully about sharing it, but I asked my lover and he was actually as keen as me for others to hear it. Consequently, here is our story, " Anne and Tod's Switchplay".

I had known Tod ever since I could remember. Our families had been friends and we'd spent a lot of time together as children. I can still see both of us running around the pool, stark naked, and without a care in the world. Tod's penis was the first I really took a good look at but given that I was the older woman of eight and he was only four, it wasn't much to look at. (It was years before I'd find out just how big it would eventually become!) Any way, I was such a tomboy compared to the other girls that I always sought his company, and we enjoyed a lot of innocent adventures together, until I got a bit older, and the breast fairy waved her magic-wand over my growing chest.

Over time, we grew up and went off to do our own things. The four year age difference was so huge when we were at opposite ends of our teens that we just lost touch. I had always kept in mind though, that even in the earliest bloom of puberty, he had the makings of a fine looking man.

I went of to university to study media and communications, and I got involved with PR quite early on. This was more because I had become, according to other people, a quite physically stunning woman. When you look good doing promo work in a bikini, it is sometimes easier to make contacts who help you break through into the business side. (That, and a few strategic blow jobs for company VPs.) Regardless, I soon carved out a successful career, even if the path was littered with discarded lovers and broken relationships.

I moved to a new company and was doing the rounds meeting the staff when my assistant confided that there was the most gorgeous man in the Graphics department, but "Wouldn't you know it, he's gay."
We walked through the doors, and much to my surprise, there was Tod! He was absolutely beautiful. And he was gay! Goddammit!

Tod and I spent a lot of time together working on some major projects, and we managed to spend a lot of time together away from work as well. We both had a tragic track record with our relationships and we seemed to find solace in each other's company. We enjoyed hearing the stories of each others' life and were so open about everything. It really was a fantastic Platonic relationship. The only thing missing was sex, although we often titillated each other with tales from our past. Tod managed to answer all my curiosities about M2M gay sex, which I found really horny in a funny kind of way, and I made him laugh with tales about my predatory and exhibitionistic adventures. There were no secrets as I told him about losing my virginity, my first head jobs (giving and receiving), my first real relationship and about having sex in a plane. I even confided about the first and only time I had anal sex, when at 18 I had a brutal lover who thought he could just slam it in there. I said I failed to see the attraction, but Tod laughed and said I obviously didn't know how to do it right.

I knew the extreme closeness of our relationship would end when he found a new lover, so I enjoyed the moment, and tried not to think how I'd eventually lose my best friend. Knowing that this time was probably getting closer, given that he couldn't possibly remain celibate much longer, I suggested that we spent a week away after finishing our latest project. I selfishly reasoned that firstly, I didn't need time one my own, secondly, he was so good looking I knew other women would be jealous, and thirdly, it was like taking my own personal masseur. Tod had truly magical hands and the world's most soothing touch. And if he found a new man, well, I'd be happy for him, if a little sad for myself.

The week went so quickly. We were staying in a cabin in a rainforest resort. The days by the pool were beautifully warm, and the nights were crisply cool. We hiked, we danced, we giggled, we made other couples jealous, we drank by the fire at night telling each other little intimacies, but we knew that tomorrow was the end.

I demanded one last massage from my gorgeous slave, and he was as willing as ever. He'd just finished my back when the lamp bulb blew. I had seen spare bulbs at the top shelf of the pantry so I went to get one. I couldn't reach so I got Tod to steady the stool while I tried again. It was one of those silly little unstable stools with the fold down steps, and I had to stand right on the top. Tod had his hands around my waist as I reached up, and his grasp seemed overly firm. I don't know why I was wearing a G-string, as I'd usually be completely naked for a massage, but for some reason I had been feeling coy. I stopped in mid reach. I could hear Tod breathing, and I knew he was looking up at me. Actually, he was looking at my ass. I looked down between my legs, and through the gap, I could see a mammoth erection in his shorts. Just wait a minute I thought, isn't Tod gay? Now I could feel his warm breath between the top of my thighs. What was happening? I felt like a spectator rather than a participant, and I couldn't wait to find out what was going to happen next. Tod pulled at the clip on the side of my G and it fell away to the floor. I've never felt so naked or open as I did then. Tod reached up with two fingers, and by making a Vsign, pushed my cheeks apart around my little puckered hole. Then he brought his thumb up between them and started rubbing my anus. This tickled almost as much as his breath, which warmly caressed my buttocks.

So many thoughts ran through my mind, but the overwhelming one was that I was going to let Tod take my anus. I could hardly believe it. Suddenly there seemed to be wetness running out of my vagina, and I could feel that my face was burning red. I could hear myself breathing with fast short gasps. What was happening? Tod's tongue had now gone to work on my ring, and I could feel it opening to each delicate touch. He seemed to be tonguing it, nibbling it, and teasing it with his fingers all at the same time. I had to hang onto the pantry doors as I felt myself going weak at the knees. Then I felt a thick oiliness and looking down I could see that Tod had pulled the vegetable oil from the pantry and had shaken some over my rear. He let it run between my cheeks but he also spread it up and over my buttocks and lower back, where it mixed with the massage oil of our earlier activities. He then started kneading, tickling and stretching all at the same time. I had started to moan quietly, and I was having trouble keeping my eyes open.
I have to get down, I whimpered, before I fall.
Sure thing, Tod said, after all Babe, you're driving this bus!
I looked down again and saw that Tod had pulled the draw-string on his shorts and had stepped out of them. I could see his erect penis in all its glory. I'd seen it 'on the slack' enough times, when it had been my turn to massage him, but I had always believed those stories that the ones that are big when flaccid don't grow as much as the littlies when they're erect. Absolutely not true!! How was my poor little asshole going to part for this thing?
Come on down slowly encouraged Tod, and I now knew that I was 'driving this bus'. He didn't move at all, and as I lowered one step, I felt my eye meet the tip of his penis. I caught his tip in the hollow in the middle of my ring, and I started trying to make small circles on the end of it. Without conscious effort, I felt his end engage with my oiled hole and gain entry through my first sphincter.
I tried to push down some more but I stopped with a gasp,
That really is some penis I'm trying to cope with.
Lift yourself up babe, Tod encouraged, and I slightly raised on tip-toes. His penis nearly came back out, but then I started to gently lower myself again, and I could feel that I was a fraction further down his shaft. My arse suddenly felt so congested and ticklish that I couldn't help giggling. I raised myself again and then relaxed and let my own weight gently pull me down.
How am I doing?, I asked, and then it was Tod's turn to laugh.
Babe, you've only just got the head in.
Given that the head I'd seen moments before looked like some obscene monstrous red-pepper, I felt I was doing well. I circled again and I could feel the rim of his head against my tight outer ring. I felt stuck. I couldn't go up and I couldn't go down.
Tod please help me I gasped, and with that he held me around the hips with both hands and calmly lifted me from the stool to the floor. His penis stayed just inside me the whole time.
C'mon Tod I cried, I need some help here.
And so Tod started moving, ever so slowly at first, and he seemed to find his friction on the outstroke. He'd pause, and then he'd ever so slowly start easing back into me. I realised that I had my eyes tightly shut and I was concentrating on these amazing sensations emanating from deep within me. I could feel my clitoris throbbing, and with a gasp of surprise, I looked down to find I was feverishly rubbing myself in front. When had I started that?
Tod withdrew completely, and I guessed that he was oiling his rod up some more. When he placed his penis back at my hole, I could feel the difference, and this time I had the most unbelievable sensation as he glided past my rings. Its hard to say which felt more fantastic; the physical feeling of opening up, swelling to receive Tod, and containing him, or the amazing psychological triumph of breaking down a personal taboo barrier. Tod was now moving so freely, and my arse was feeling so good I can't describe how I felt. Lets just say that I was on the fast track to Orgasm City.
And then I started laughing again. Not only was I enjoying the greatest sex I'd ever had, but I was fulfilling every woman's fantasy of converting a gay man! And the most gorgeous one at that!!

Tod was maintaining a delicious slow rhythm which was pushing and pulling my arse and making it feel so full and hot. I kept working on my clit, and I could feel myself start to tighten up. I knew it was going to be an absolutely sensational orgasm, and I concentrated on the centre of these sensations. Tod stopped.
Whats the matter? I hoarsely asked.
I want to come face to face with you babe, he demanded.
Now I was absolutely shocked. I'd heard enough of Tod's stories to know that he mostly preferred his lovers bent over before him. I knew that two guys could do it face to face, but I knew Tod only did this when it was 'True Love'. Maybe this was even more special than the beastly fun I'd been enjoying.
I want to see your face when you come, Annie…..please?
Oh wow, talk about spinning a girl out!
I pulled away and rolled over so that I was on my back. I pulled my legs as high as I could and rocked my pelvis back. Tod threw a pillow under my hips and knelt in front of me. His penis dangled forwards and exactly met the open hole of my bottom. He gently pushed forwards and it felt like he was trying to push into a puffy marshmallow. The feeling was again superb, and yet it was very different to the feel of his last entry. I realised I had stopped breathing, and was just staring at Tod. Our gaze was locked, and I felt so awkward. It was like I had never had sex before. There was such an intense feeling between us that I nearly cried. As I stared at Tod, I could see that tears were welling in his eyes as well.
Come one, Lover, I barely croaked, what are you waiting for?
Tod barely moved in and out as I felt an enormous surge stirring through my pelvis. Tod clenched his fist and ran the knuckles back and forth over my hood and clit. I gasped at the intensity of the tremors which shook me, and I could feel a wild spastic clamping from my rectum. This sent Tod over the top. Even through my own orgasm, I could feel him unloading into me. His penis pulsed and pulsed and he launched its hot load into my burning bowels. I could feel it in my arse, running out of my arse, and between my legs. It was like boiling oil. I gasped and almost passed out.

Tod leant forwards and relaxed onto my chest. I could see that he had tears on his cheeks.
What's wrong? I sighed.
Annie, I've always loved you…ever since we were little kids. You're the only woman I've ever wanted. I'm so so sorry.
Sorry? Sorry for what….?
Sorry that our only opportunity was this, and sorry that you won't really want me again.
My darling Tod, if you're saying what I think you're saying, don't apologise….and this sure needn't be the last time!

And that folks is how I ended up with my wonderful Toddles, my gay male lover. For sure, I know he looks at other guys, because they are what he finds physically attractive. But I worry less about him straying than other women do about their hetero partners. I know he's mine forever. And I don't have to worry about being the best pussy he's ever had……

Kisses, Anne.