Wedding Day Surprise

Editor's note: this story contains scenes of incest or incest content.

*****

You might say I had an unusual childhood. My older sister had wanted Mum to have a girl when she was pregnant with me. She got over her disappointment by treating me like a girl from an early age. She'd dress me up in girly outfits and we would play with dolls. My father had never been married to Mum and had left her to her own devices after my sis was born. He never visited us or sent birthday cards so we never knew who he was. Mum explained that he'd kept in touch in the early years sufficiently enough to impregnate her with another child (Me). But even Carol, my sister didn't know what he looked like.

I developed an interest in girls things and would play with dolls even when Carol was out. Mum was out working a lot leaving Carol in charge of looking after me. When I started school Mum was worried I was becoming an oddball and would get teased by other boys so she told Carol that the dressing up had to stop. But by then the pattern had become established. Carol wanted to play dress up and I was happy to go along with it. From then on our games would happen secretly in the home and I would dress as a boy at school and when Mum was home from work. I had established a bond with my sis so we went everywhere together.

I put my name down at school to attend a show about ballet dancing. It was only afterwards that I realised I had been the only boy from my school to go. Boys in my class had already picked me out as different with my long hair, glasses and tendency to hang around with my sister in the playground. Comments were made and I became even more isolated from the other school boys but I tried to ignore it. Carol stuck up for me and so did a few of her female friends but even some of the girls at school joined in the name calling. I took a perverse pleasure in the comments and did not make any attempt to change my behaviour. Sometimes I'd be deliberately provocative which I came to believe gave me status amongst some children and a grudging respect.

As I approached puberty Carol found a place at Uni and I realised I would be without my best pal. Her college was not too far away and she planned to come home about once a month but I was sure I'd be lonely without her.

"Perhaps you should stop now you're getting a bit older Davy. But if you can't there'll be clothes in my room you can try on. I'll put them in the wash with my things when I'm home."

"Thanks Carol." At least I had the option to continue. I wasn't sure if it was something I wanted to do.

"You don't seem to have many male friends." Carol said kindly. "Perhaps it would do you good if you made the effort to find one. There are a few gentle, intelligent blokes with an appreciation of books and good films out there. Have you ever tried going on one of those chat rooms on the internet? You can be totally anonymous at first."

"No Mum says they're dangerous. Lots of pedos pretending to be fourteenyearolds. Trying to trick you into meeting them."

"Yes, she's right. But you're a bright kid. Don't meet them. Those bastards don't have the patience to spend much time grooming you. Just be wary. The fact that you know the dangers will keep you safe. I'll send you the details of the one that I use."

Carol's advice helped me not to miss her quite so much. I did find a couple of friends through chat rooms. Mum was working two jobs now to help pay for Carol going through Uni so I made the meals and did most of the household chores. I particularly enjoyed doing the ironing.

Mum realised I was missing Carol and made more effort to spend time with me. We'd sit together on the sofa of an evening watching TV, a happy time for me. I left school at sixteen and found a job close to home. I was painfully shy around girls and by the age of eighteen I'd still not found a girlfriend near home although I was in contact with a girl from the chat room I used.

It was a few months after my eighteenth birthday when something unusual happened. I'd often be wearing a dressing gown and pyjamas after supper whilst I was watching TV with Mum. We'd sometimes cuddle up close on the settee and one night she noticed my penis thickening. It seemed natural for her to casually stroke it whilst we sat together. Nothing was said. There were always tissues within reach in case I spurted which happened every now and then.

Once when we were in front of the TV cuddling as usual I came back from the toilet and found her seated with her legs wide open. She was not wearing panties. I knelt before her and she nodded. Again we didn't speak. My experience of sex was very limited. She'd helped me out so it seemed natural for me to place my mouth on her pussy and lick. Cunnilingus was something I'd thought about and it was just as wonderful as I'd imagined. I could tell Mum was enjoying it as she began drawing her breath in deeply and letting it out in short bursts. Her panting increased in speed until she was holding my head close to her with both hands and thrashing about. I was happy to receive a squirt of her juices into my mouth which signalled her orgasm. Mum was not greedy, she only slipped off her panties after that about once every two months.

After that we'd kiss properly on the lips when she went off to work and on her return. I liked the taste of her lipstick and didn't wipe it off around the house. We got used to seeing each other naked at home occasionally, not as a prelude to sex, just when changing or coming out of the shower. Mum was concerned that I still hadn't found a girlfriend, she said she wanted me to know what women looked like in the nude. This seemed a strange thing to say when the internet was full of pictures of naked women but I accepted it without comment.

Another year went by and I was becoming desperate to lose my virginity. I was hoping that the friend I'd made in a chat room might eventually become a sexual partner. I'd been having chats with Monica for three or four years now. We'd become confident enough to communicate via WhatsApp over the last six months. Our chats had increased to daily exchanges once we had seen pictures of each other. We rarely sent messages any more as we were now able to "Facetime" each other. Monica also lived in England but we'd so far not actually met. She lived about seventy miles away. We had lots in common. Both about the same age, similar interests, both did office work. I decided I'd held off from meeting her long enough.

"Hello Mo, I've enquired about trains as you suggested and it'll be a simple journey to your nearest train station, only one change. I'll arrive at 10am. Mum is happy for me to meet you since she had that long chat with you over the phone. I can't wait to see you after all this time. Will you come to the station? I'm scared I'll get lost otherwise. I've never been to Scarborough."

"Course I'll come to the station David darling. It was worse than my worst job interview speaking to your mummy. The things she asked me! But truth be told she doesn't know you like I do does she? You will wear your best pink panties for me like you promised won't you sweetie?"

"Yes, but I want you all to myself when I visit this first time as we agreed. We can leave the inevitably embarrassing introductions with your family to another day."

"They don't even know you're travelling over. I'll talk to them about it in my own time."

"As you wish. I'll see you Saturday. I look forward to my first hug."

"There'll be kisses too, no doubt." Monica promised.

Neither of us wanted to break contact so there were more exchanges before one of us rang off. We'd talked endlessly about ourselves over the years and I'd left nothing out apart from what Mum and I had got up to. She knew about the handjob and that I'd licked a woman to orgasm but not who the woman was. She was comfortable with the fact that I was a virgin whilst she was fully experienced sexually. Apparently there had been three men in her past but this did not bother me in the slightest.

She came to pick me up in her dad's car. I'd forgotten she'd passed her driving test. I'd failed mine twice but was determined to keep trying. I couldn't believe that a girl so gorgeous wanted to spend time with me.

"You're not so bad yourself," she said when I expressed my surprise. "I want someone gentle and kind like you. I fell for you a long time ago, before we could see each other on WhatsApp. You could earn a living as a writer. It was your words that seduced me my darling."

We kissed open mouthed sitting together in the station car park with people walking past. We were oblivious. Lost in each other's arms. My penis was fully erect by the time we stopped but I wasn't planning to lose my virginity there in the car park.

Monica drove me to the start of a walk she knew out in the country and we strolled hand in hand along leafy lanes and paths with views of the sea. I was nervous of course but also happy to be alongside the friend I'd corresponded with for most of the years since my sis had left home. We talked easily together without holding back, the words tumbling out in a torrent at first each of us having to stop at times to let the other person get a word in.

"I've imagined this in my head many times Mo but it's ten times better than I thought it would be. You're everything I thought you'd be and much more besides." I said. "It's hard to believe it's really happening."

"Of course this is all new to you isn't it my darling? I've not told you everything about myself. I just hope you're going to like what I've got planned for you. I'm right about you being submissive aren't I?"

"Submissive? I suppose I am. My sis used to boss me about a fair bit and I quite liked that. As you know she tried to turn me into a girl and she just about succeeded. You said you liked my feminine ways didn't you? She influenced me and there was a time when I wanted to be a girl."

"It's what first attracted me to you sweetie. Your crossdressing excites me, I love your gentle feminine ways, I think we make a good fit as a couple. We've talked about spanking haven't we? I never asked you if anyone ever spanked you."

"Not often. Mum gave me a spanking if I was a naughty boy a long time ago. I've sometimes wished she'd do it to me now I'm grown."

"Mmmm. That's interesting, maybe you're more submissive than I thought. I'd love to...er.. er."

"Give me a spanking?" I interrupted. "I'd love it if you took me over your knee." My voice sounded quiet, more feminine, I could feel my face heating up.

Monica's eyes sparkled. "On your bare bottom?"

"Is there any other proper way?" I whispered this, feeling a stiffening between my legs.

"I know a quiet little beach not far from here. If there's no-one around I could show you how a grown up spanking feels."

The turn taken in our conversation was a complete surprise. Monica was asserting herself. Well I was hoping to somehow get sexual today. But would this do the trick? Hardly a conventional way to proceed. And would she still want me after she'd seen my bare bum?

"Drop your shorts, darling, let's see those panties."

Monica was sitting on a rock in a small alcove on the sea shore. There were a few seagulls around but no humans. It was warm and sunny. I removed my sandals and stepped out of my shorts kicking them out of the way.

Mo mimicked the whistle a building site worker might make to a pretty girl passing by. I enjoyed it. My cock stiffened. Her face changed, becoming stern.

"I'm very displeased with you. I didn't give you permission to wear my panties. Pull them down to your knees and get across my lap."

"Yes mummy, I'm sorry." I'm not sure why I called her mummy. I was fully stiff now but as the slaps came raining down my erection subsided. Fantasies about spanking are never the same as the real thing.

When it was over we stood together and she kissed me passionately. I loved the way her tongue darted in and out of my mouth. We are the same height but I felt her superior strength as she hugged me tight. My arms went around her neck as if I was the woman and it felt wonderful.

She broke the kiss, her breathing laboured.

"You're mine now aren't you? Show me. Like a good girl." She hitched up her skirt and dropped her panties to the floor stepping out of them and placing her legs apart.

I knelt before her and started licking her pussy. The smell and taste was different from Mum but I enjoyed it immediately. This was what I'd dreamed about ever since we started writing to each other. I know I'm not a macho male only interested in my own pleasure. It's my job to make sure Mo gets what she wants. My needs will always be secondary.

The lay-by where we parked was deserted when we returned. I was now wearing Mo's panties and she was in mine. She was very relaxed after having her orgasm and a bit giggly. Before we set off back to town she unzipped me and took my penis out.

"Sorry it's not the biggest Mo. You're not disappointed are you?"

She laughed. "You're forgetting. You sent me a picture, when was it, over two years ago? It's fine, in fact it's lovely." She bent and kissed the end then looked around unsure. "You've never had a blow job have you dear?"

"Er, no, as you know I'm not very experienced."

"I'll just wank you for now. We can talk about sex to help you stay hard." She pulled out a tissue and handed it to me.

"Tell me about your hand jobs and your cunt licking."

What was I to do? Mum always told me to tell the truth. I knew I was taking a risk. She might never want to see me again. I went with my gut feeling. Mo knew everything else about me. She was unshockable.

"I never told you the whole truth. I'm sorry Mo. I should have, I don't like secrets."

"Spit it out Davy or I'll stop pulling on your tiny cocklette." Her comment made it jerk. I wanted her to joke about my penis size. I loved the humiliation.

"It was Mum, we cuddle on the sofa in our pyjamas. She... She... strokes it. Sometimes I spurt. It just happened. I didn't want it to stop."

"And did you lick mummy, you dirty girl?"

"YYYessss!" I bow my head, red faced, waiting for the angry reaction.

"Good girl." Mo says with enthusiasm. "I expect it's still going on isn't it?"

"Yes, but I'll stop, I'll tell her as soon as I get home."

"You'll do no such thing! Mummy likes it doesn't she? Promise me you'll keep on with it. Fuck her if you want, I don't mind. This is so hot!"

I'm flabbergasted by Mo's reaction. A sudden image springs into my head of me lying between Mum's legs driving my penis in and out of her pussy and semen spurts out of me before I've got time to catch it in the tissue.

"Oh Davy, did I say something to make you cum? My pretty little girly boy. I never would have imagined that. With Carol, yes, you were so close weren't you?"

My emotions were in turmoil. Tears sprang from my eyes. Mo hugged me to her.

"It's okay darling, Aunty Mo will make it better." She kissed away my tears. I sniffled, wiping my nose with the tissue she gave me. She produced another tissue and wiped the cum off bits of the car. I noticed there was some on the gear lever and giggled like an hysterical girl. In fact it was exactly how I felt at the time.

"You've bottled that up, now that you've told someone, you'll find that in time you'll feel better for sharing it."

"Thanks Mo. I wanted to tell you. The time never seemed right."

She drove me back to Scarborough. We were having a meal in a cafe when she said.

"I don't want to rush things so when you get home I want you to think seriously about our future together. We've never talked about marriage have we? It will be a bit different from some marriages if we decide to marry. Perhaps we should stay single as we are. You see I want you to agree to me seeing other men if we do tie the knot."

I was disappointed to hear her say this but perhaps the very kinkiness of her comment caused my penis to swell.

"See other men?" I whispered this, looking around to see if there was anyone within earshot but it seemed not.

"Yes, you'd be okay with it if I fucked other men wouldn't you sweetie?"

"I don't know...I..."

"Don't answer now darling. It's okay, I know it's a lot to take in. Think about it and let me know next time we meet." She reached under the table and took hold of my penis briefly. She smiled wickedly.

"Your little soldier seems on board with the idea. Tell you what, I'll book us into a nice B and B with en suite facilities for the next time we get together. It'll be lovely to spend the night together won't it sweetie?"

"Er, yes, I'd like that."

Travelling home on the train I tried to make sense of what had happened. I was still a virgin and hopefully that would be resolved the next time I saw her. I decided to take things one step at a time. But I felt that the day had gone well. She'd actually talked about marrying me. I could hardly believe it.

"Well, what do you think of our little lovenest?" It was another weekend in Yorkshire two weeks after my trip to Scarborough and we had just booked into our Bed and Breakfast. I'd got away from work early Friday afternoon. We were in a small village in the Yorkshire Dales. Mo had her dad's car again. I hugged her and kissed her passionately by way of answer.

"Shall we test the bed springs sweetie? Strip off those trousers and panties first." She was removing her own clothes as she spoke. Once naked she lay on the bed, a vision of loveliness.

"This'll help us both to relax. You'll see. Let me stroke you. I want you nice and hard." She reached for her discarded panties and wrapped them around my member as I lay next to her on the bed.

"You like the feel of my panties rubbing against your prick don't you sweetie? They are sopping wet with my juices. I'm ready to feel you inside me. Would you like to plunge your cock into my cunt? I want you to fuck me. It's fine if you spurt quickly. I can easily get you hard again later."

Her dirty talk and stroking helped as we moved into the missionary position. She kept hold of my penis and placed it at the entrance to her vagina. For a second I was losing my erection but Mo squeezed and stroked it back to life again.

"Push forwards carefully darling." My phallus slipped inside easily. The feeling was so wonderful I almost spurted immediately. But I wanted to make it last, revel in the sensations around the cherry shaped end released from where it is normally hidden behind my foreskin. It's so incredibly sensitive that I couldn't help moaning as I moved it in and out. In less than half a minute I was unable to stop myself from ejaculating causing my penis to shrivel.

"You did well darling. Let's unpack, have our evening meal, then we can go again. I want to go on top this next time. You'll enjoy me doing all the work you sissy girly boy won't you darling?"

"I imagine I will Monica dear." I smiled. She was right, I was a lot more relaxed. It only took half a minute but my virginity was a thing of the past.

My second attempt at fucking lasted much longer. I loved Mo taking the lead. I'd brought along my girly clothing as she'd instructed and she helped get me all dolled up in bra, stockings and suspenders, lipstick,wig and makeup then had me pull my dress up and remove my panties whilst she fucked me with the rest of my clothes on. She was quite ferocious and threatened to tie me up next time. Whilst she had a noisy orgasm this time it wasn't enough for her.

"I need to sit on your face darling." She moved up the bed and lowered herself onto my mouth.

"That's it sweetie, lick up your spunk. There's two deposits up there. It turns me on to think of you swallowing your own cum."

I was okay with it. It wasn't a fantasy before but I found myself getting excited as she dominated me in this way. Mo was obviously getting a lot from it and that in itself was good. As for me I was enjoying submitting to her, tasting my spurtings. Her second orgasm was noisier than her first.