Encounter with an older man
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My First Encounter With A Man free porn video
Number 29 of a series of individual stories.
My first encounter with a man by SONIA
(email [email protected] - Please send comments)
Chapter 1 - Sally Anne's Suggestion
My wonderful wife Sally Anne and I have had many adventures when
I have dressed in lingerie or fully as a woman. I always let
Sally Anne dictate how and when I dressed up. I did not dress
often, maybe once or twice a month but dressing had developed
into a big part of our marriage. Our sex life was fantastic and
we made love almost every day and sometimes several times in a
day but when we had sex when I was dressed it was out of this
world.
In the early days I had been very much a man in panties but over
time had progressed to dressing fully as a woman although still
preferring sessions when I was a man in panties. We had close
friends, Kate and Karl who had very similar interests to
ourselves with Karl also loving dressing as a woman.
I think the thing that first started to confuse my feelings was
when Sally Anne had dressed in a rubber outfit with black rubber
panties that had an integral rubber penis that protruded from
them. She loved the outfit because the penis was double ended
and half was buried deep into her. With me dressed in a sexy
woman's outfit she had had me bend over and she had used her
rubber penis to have anal sex with me - and I had loved it.
Things might not have gone further if it hadn't been for Sally
Anne's work partner, Stacey. Stacey had found out about my
female side and then confided in us that she was a transsexual
who had lived as a woman since she was 16. She had joined us for
sexy weekends on several occasions and inevitably had had sex
with me - and I had loved it.
I had tried to convince myself that Stacey was so close to being
a woman that it was not a homosexual affair but as time went on,
particularly when I was dressed in some wonderful sexy lingerie,
I found myself looking at both men and woman and fantasising
about them both.
Sex with Sally Anne was still the most wonderful thing and we had
a fantastic sex life. We had a semi open marriage in so much as
Sally Anne had had sex with Karl and I had made love to Kate and
Kate and Sally Anne had had lesbian sessions and obviously Stacey
had made love to both of us but so far we had gone no further.
Sally Anne had employed a new member of staff, called Justin, at
their advertising agency. Justin was about 3 years younger than
us, good looking with blonde hair and was well built and quite
sporty. I met them at lunch when he had been working at the new
job for about a month and found him to be really friendly but
shy. Sally Anne was chatting to him like she had known him for
years and we all got on very well.
That evening Sally Anne confided in me that she really fancied
him and said with a grin, "I bet he's ace in bed too."
My penis twitched with the thought of Sally Anne having an affair
with Justin and I started planning.
"Would you like to have sex with him?" I asked.
Sally Anne stopped dead and looked at me and replied, "Well yes,
sort of. It would be fun to see if he is as good as he looks.
But I love you and don't want to have affairs. Its different
with Kate and Karl."
I thought for a minute and then said, "I'd love you to have sex
with him if I could watch secretly."
I had always enjoyed watching Kate and Sally Anne having lesbian
sex and liked the idea of watching her with another man. I was
planning quickly! I decided to cut a hole in the wardrobe door
and to fix a one way mirror over it and to watch from in there
and I explained my plan to Sally Anne.
"I would find it really exciting to have you watch me wearing
just your sexiest lingerie - Oh God I'm getting excited thinking
about it."
I suggested, "How about I dress up and you arrange to meet Justin
at a pub and I can sit nearby and watch as you let him chat you
up. You can say I am away for the night and suggest coming back
for coffee. If you take the long route home I can get home ahead
of you so I can strip to my lingerie and get in place by the time
you get back and then watch you make love."
"Oh that sounds great fun. Darling I need you now!"
We quickly stripped off and made love, each fantasising about our
planned game.
Chapter 2 - The big day
Over the next couple of weeks Sally Anne made more and more
suggestive advances to Justin and generally took every
opportunity to touch him when she was discussing anything. She
dressed a little more flirty and wore a bit more makeup and
reported back to me that on several occasions she had spotted him
with an erection, carefully trying to disguise it.
The plane was set for that Friday when they had an important
client meeting in the afternoon and Sally Anne suggested a meal
afterwards to either celebrate if they won the contract or
commiserate if they didn't. Justin accepted eagerly.
When Sally Anne dressed for work that day she certainly did not
put on her normal work lingerie! She put on a set of emerald
green satin full cut panties, suspender belt and bra all with
deep layers of white satin lace trim. She put on black stockings
and a matching waist slip and then on top an emerald green satin
blouse, black A line skirt and black business jacket and finished
with black high heeled shoes that were just low enough to be
business like but worn with the lingerie would give the perfect
accompaniment.
"Darling are you sure about this?" She asked holding me in her
arms.
"So long as its me you love then I'm happy."
We kissed, said good bye and she set off to work.
I had time enough to come home and change so I sorted out my
outfit and lay it on the bed ready. I decided to wear my lilac
satin corset with black lace trim with its front black lacing
with its matching full cut lilac satin panties with black lace
around the legs and waist band and a black lace flower motif on
the front, black stockings, and black knee high boots. On top
I opted for my lilac satin skirt with small flowers on it and a
soft black cashmere short sleeved jumper. The skirt length was
over my knees but long enough to be respectable.
I intended to have a really sexy time so I also took out my anal
vibrator and put it ready.
I was very excited now and decided to wear panties to work and
slipped on a pair of black tights and some frilly white sissy
panties on top and then finished dressing.
The day at work dragged somewhat but knowing how I was dressed
made the day bearable. I knocked off work early and went home,
thinking all the time about Sally Anne and Justin. I had a bath
and shave and then put on my panties and then my corset,
loosening the laces first and fastening it around me and then
lacing it as tightly as I could, slipping my silicone false
breasts into place as I did so - it felt wonderful gripping my
body. I put on the stockings with some difficulty as bending was
not easy, and then my boots. Looking in the mirror I thought I
looked incredible in my outfit but still without my wig and
makeup.
I sat at the dressing table and careful fitted my wig and did my
makeup and I was now a reasonable looking woman in sexy lingerie.
I slipped on the petticoat and was about to finish dressing when
I remembered the anal vibrator. I put some lubricant on it and
dropped my panties and slipped it into my anus feeling it stretch
me wide, filling me in an incredible way. It eased in until I
felt as though I could take no more and then the narrowed end
slid in and was gripped by my back passage muscle, stopped from
disappearing fully by the wide end plate which sat against my
bottom. I pulled up my panties and gently sat down on the bed
to get used to the feeling which was bliss and once again my
thoughts went to what it would be like with a man!
The vibrator had its batteries internally but had a small wire
with a switch so that you could turn it on and off and I put this
in reach at my waist. I put on my skirt and jumper and I was
ready.
Sally Anne had booked a table for dinner and I had booked a table
beside theirs. I set off towards the restaurant feeling very
excited. I was there a few minutes early and sat in the bar and
ordered a drink. The restaurant was not very full and luckily
there were no other single people there as I did not want any
unwelcome advances.
At eight o'clock the door opened and in came Sally Anne and
Justin and by the look on their faces they had won the contract!
Sally Anne looked at me and winked but then ignored me and
started flirting with Justin.
I suddenly wished I had worn a panty girdle as seeing them
together gave me an erection which I tried to disguise. Sally
Anne ordered drinks and I was offered the menu. I was too
excited to eat so ordered a simple meal and a half bottle of
wine.
Sally Anne had her hand on Justin's leg and was talking to him
and her body language left no confusion of her feelings. As they
chatted I saw Justin put his hand over hers and then she stopped
talking to him turned to him and gave him a quick kiss on the
cheek. He blushed and then smiled and they went on talking but
now holding hands. They ordered their food and Sally Anne stood
up and said she was going to the ladies and started to walk away
from him. As she moved across the bar which was now empty apart
from us she dropped her hand bag and bent from the waist to pick
it up and then carried on to the toilet.
The view she had just given us both was of her petticoat and her
stockings straining at the suspenders.
I covered my penis with my handbag and followed her to the toilet
and once inside we fell into each others arms and kissed
furiously. I told her off for being so naughty flashing her
lingerie to Justin and she turned to me, lifted her skirt and
petticoat and said "Do you think he will like them?"
She looked really sexy and again my penis strained against my
skirt.
"I think you need a little help," she said and pushed me into a
cubicle, lifted my skirt and extracted my erect penis from my
panties and took it into her mouth. My level of excitement was
such that I lasted no time at all and soon was pumping my semen
into her mouth. She slipped me back into my panties and stood
up and kissed me sharing the salty taste of my come with me.
"Enjoy the show later!" she said and went back to the bar.
I followed a little later and went to my table. They joined me
and I saw they walked in linked arm in arm. During the meal I
saw Sally Anne lift her foot and put it on his crotch and he
grinned at her, albeit blushing slightly.
As I sat there the feeling of the anal vibrator was bliss but as
yet I had not turned it on - that joy was for later.
I paid my bill and with my hand bag held in front to disguise my
penis I headed for the car. Once in the car I hitched my skirt
and petticoat up and with my panties and stockings on show I
headed for home. I parked the car in the next street and walked
to our house and let myself in. I went into the living room and
stood in darkness in front of the window and took off my boots,
skirt, petticoat and jumper. I stood there for some time exposed
for all to see but shielded by the darkness.
Finally I headed to our room, opened the wardrobe, went in and
sat on the stool I had left there feeling the vibrator again push
into me. I was just about to close the door when I saw a note
stuck to it and I read it.
'Darling if tonight goes to plan I will be thoroughly shagged by
Justin. Knowing you will be watching will give me an incredible
thrill. Enjoy the show and see how many times you can come
through the evening - but keep quiet!!'
I was incredibly excited and relieved that she wanted me to
masturbate while watching her. I closed the cupboard door and
fastened the internal lock I had fitted so I could not be
discovered by mistake. By the light from the moon I could see
through the mirror the bed and in fact most of the room.
To make the time pass I turned on the vibrator and caressed my
body feeling my corset as it gripped me and my sexy panties. The
vibrator purred away almost silently and the intense excitement
of what I was doing soon had my penis straining at my panties.
I loved the idea of coming in my panties while I watched Sally
Anne and Justin but wanted to save that for then but I knew I was
on the verge of coming so I grabbed a tee shirt from the shelves
beside me and took out my penis and masturbated into it. It felt
wonderful as I came with my muscles tightening around the
vibrator.
I cleaned myself up and turned off the vibrator and rearranged
my penis in my panties ready for Sally Anne to arrive and had
just finished when I heard the door open downstairs and Sally
Anne and Justin entered. I could not hear too much but heard the
chink of bottles and then the sound of them coming up stairs.
The door opened and the light went on and suddenly I could see
everything. It was really weird sitting there at a 3ft by 2 ft
window looking at Justin and Sally Anne but they could not see
me.
"I'm really not sure about this," said Justin, "It does not feel
right in your room when your husband is away."
"We have a fairly open marriage and I fancy you a lot."
She went to him and kissed him and I turned on my vibrator and
as waves of sensation flooded through me I watched.
Sally Anne started undoing Justin's shirt and then undid her
blouse and as they both dropped their shirts on the floor they
again kissed and Justin's hands roamed over her breasts.
"Take off your trousers and underwear and lie on the bed," she
commanded and then turned to the mirror as if checking her
appearance and gave me a smile.
Justin undressed and I was amazed at the size of his penis, it
was noticeably bigger than mine and stood out rigidly in front
of him.
He lay back on the bed and Sally Anne then turned to him and with
her eyes locked on his she slowly undid her skirt and let it drop
to the floor and then she dropped her petticoat and was standing
in front of this comparative stranger in her bra, panties and
stockings.
This was too much and I came, pumping my semen into my panties
and my body shuddered with the pleasure. As I regained my
composure I wondered if I had made a noise and saw Sally Anne
looking at the mirror with a knowing look but Justin was so
intent on her sexy image that he showed no sign of hearing
anything.
Sally Anne turned back to Justin and took off her bra and went
over to him, opened her drawer and took out a condom and bent
over his penis, kissed it and licked the end and then rolled on
the condom.
Justin pulled her to him and they kissed and cuddled and petted
each other becoming more and more frantic as their passion grew.
I came the second time when Justin pushed Sally Anne back, pulled
down her panties and buried his face between her legs. She was
soon thrashing around on the bed, locking her legs around his
head and coming with a gasp of pleasure.
She then lay back on the bed and spread her legs wide and he
rolled between them and as he entered her she gave a gasp of
pleasure.
This was the most sexy thing I had seen for ages and I was rigid
in my panties but what brought me to my next orgasm was when he
withdrew, turned her over and lifted her bottom towards him and
entered her from behind. Sexy though this was the thing which
turned me on so much was that he pushed 2 fingers into her anus
as he entered her and seemed almost more intent on caressing her
anus than her vagina although he was thrusting gently in and out.
Suddenly I realised that I was pulling myself down onto my stool
to thrust the vibrator deeper into me and imagining that it was
Justin making love to me and as I fantasised my sissy penis
erupted again.
Their love making went on for a long time until finally they
collapsed in each other's arms exhausted. Suddenly I worried
that I was going to be stuck in the wardrobe all night if they
fell asleep but hoped that Sally Anne would find a way of saying
he can't stay the night.
Sally Anne then started talking to Justin saying, "That was
wonderful. The way you caressed my anus when you made love from
behind was wonderful. How on earth did you learn tricks like
that. It felt as though you knew where every nerve ending was
and it felt amazing. It definitely heightened my orgasm."
What happened next took us both by surprise. Justin went red,
started mumbling and then got up and started dressing saying he
had to go.
Sally Anne got up as he dressed and stood there in just her
stockings and suspender belt with a puzzled look on her face.
"Did I say something wrong?" she asked.
"No. I'm .. I'm tired. That was a wonderful evening."
With that he went. I let myself out of the cupboard and soon
Sally Anne returned and we kissed furiously.
"Up to the end that was amazing," she said, "Knowing you were
watching me secretly was mind blowing."
As she said that she put her hand out to the front of my panties
and felt the wetness but also the erection that had hardly
dropped all evening.
"You certainly seemed to have enjoyed the show but your still not
finished yet are you darling?"
She extracted my penis from the come soaked panties and said, "I
can't have this messy thing make love to me." She then dropped
to her knees and licked my penis clean and then guided me to the
bed. As I entered her I had the image of Justin making love to
her in my mind and together we had blissful, loving sex.
Chapter 3 - Justin
At work the next week Justin acted as though the night with Sally
Anne had never happened which puzzled us both for some time.
The following weekend Sally Anne and I decided to go to a bar
where cross dressers tended to go for a fun evening. My problem
was that I loved dancing but loved it best when I was dressed in
some flirty skirt. The bar we went to had a mixture of gays,
transsexuals and also cross dressing couples like us and we could
go and have a fun evening dancing together without causing any
discussion.
I had on a sexy black full circle skirt and red satin blouse with
my favourite set of red satin lingerie with black lace trim.
This was the set I had first worn when I had started wearing
panties and always made me feel sexy when I wore it. I loved the
full cut panties and the layers of black lace like tennis
knickers. I also loved the skirt and the fact that if I did a
quick turn it flared out flashing my stockings.
We had been dancing for some time and then sat down for a rest
when suddenly Sally Anne stopped dead in mid conversation and her
mouth dropped open.
I turned to look at what she was looking at and on the dance
floor saw Justin but what we both started at was who he was
dancing with - a young blonde haired man!
"That explains it all," she whispered.
The record changed to a slow one and Sally Anne got up and
whispered to me, "If I go outside join me in ten minutes at the
side of the bar."
I watched her then walk across the dance floor, tap Justin on the
shoulder and from what I could lip read she asked if she could
interrupt for a dance. Justin went white and his partner stepped
back a step. Justin said something to his friend and then Sally
Anne took hold of Justin and they danced away.
As they danced I could see they were talking and then as she had
suggested they went outside. I timed 10 minutes and followed and
as I stepped from the bar and walked around the corner they were
standing there and Justin was crying on Sally Anne's shoulder.
Sally Anne said to me, "Justin has just been explaining to me
that he is bisexual and I was trying to reassure him that I
didn't mind but can't seem to convince him. I'm sorry Justin,
how rude of me, I have not introduced you. Justin this is my
husband. Darling this is Justin."
I put my hand out in a manly way which seemed incongruous with
the attire I was wearing and said in my normal voice, "Pleased
to meet you."
Justin's mouth dropped open and he stared between Sally Anne and
I with a look of total disbelief.
I said still in my male voice, "Would you like to join us for a
nightcap at home? We can chat about things easier their."
Justin stood for a second and then nodded and followed us as we
headed for our car. He said little on the drive home and lagged
behind as we went into the house but I encouraged him and he came
in. I poured drinks and we sat down in the living room.
We spent the next hour frankly discussing each of our situations.
Justin was amazed at my story and of some of our adventures and
then explained his situation.
Justin had known from an early age that he fancied both men and
women but had really been too shy to take it much further until
he had left home. Since then he had had a few affairs with men
and women but nothing serious and nothing for some time.
"When you picked me up on the attention I paid to your anus I
thought you had guessed that I was bi. I then picked up the
friend I was with tonight as I really felt the need of some male
company."
"Aren't you worried about aids?" I said thinking that he had made
love to Sally Anne.
"I'm very careful and always use a condom. I have not had a
homosexual affair for over a year and had an HIV test about 8
months ago and it was clear. I don't have casual sex but enjoy
being with another man particularly when he is the more feminine
side."
Sally Anne was watching me and suddenly she said, "Would you like
to dance with my husband. He loves dancing. Sonia you would
love to dance with Justin wouldn't you."
Was it the way I had looked at Justin that Sally Anne had seen
and recognised or the way I behaved when she had used her dildo
on me and I had made love to Stacey. Whatever the indicator
Sally Anne had recognised that I so wanted to be held in Justin's
arms and to dance and to ...."
Justin looked panicked but when Sally Anne asked if he minded if
she watched and used her vibrator that he realised she was
serious.
She disappeared out of the room and while she was gone Justin
looked at me and said, "Are you sure? I have to say that I find
you incredibly sexy dressed so sexily."
I got up and put on a record making sure I bent from the waist
to give him a flash of my stockings. I dimmed the light and went
over to him and offered him my hand. As he stood and took me in
his arms Sally Anne returned having taken off her dress and bra
and sat in a chair with one leg over each arm and then used her
vibrator on her clitoris, over her satin panties with one hand
and caressed her breasts with the other.
Justin held me close and I moulded my body into him. He was my
height so our faces were close and as we danced he said, "I don't
believe what is happening. Surely with a wife like Sally Anne
you don't want to get involved with me."
"Sally Anne and I don't have a conventional marriage. The way
I am dressed demonstrates that. I loved it when you made love
to her and I want you to make love to me."
There I had said it. There was no going back now. Justin looked
at me and to reassure him further I turned to him and kissed him.
As I turned to face him to kiss him I felt his rigid penis in his
trousers and he felt mine sticking through my skirt and panties.
We danced on and as we did he started grinding his hips against
me and I got more and more excited.
Sally Anne let out a gasp and said, "Won't you two hurry up and
make love. I've orgasmed several times and you haven't even
started yet.
Justin again looked concerned and to reassure him I took the lead
and undid his shirt and helped him slip it off and then his
trousers. Sally Anne had brought the KY jelly and condoms down
when she had changed from her dress and so I pulled off his
underwear and went to get them.
"How do you want me?" I asked, "Shall I undress or will you make
love to me as I am?"
The heat of the moment had taken control and Justin half panted
out, "Keep your clothes on."
He had taken off his clothes and stood before me naked and just
as Sally Anne had done I bent down to his penis and kissed it and
licked it and then rolled on the condom.
"You were watching!" he said and groaned as I stood up and
cuddled him letting my skirt skip over his penis.
I put some cushions on the floor and lay down on my front with
my bottom raised on them and flipped up my skirt so my stockings
and panties were exposed. Justin applied some KY to the condom
and then pulled the back of my panties down and I felt him smear
some KY on my anus and then he lay beside me. I had expected him
to enter me straight away but instead he rolled my head to him
and we kissed and as we did so his fingers slipped into my anus
and gently teased my inner muscle. This was fantastic and I lay
there and let him dictate the pace.
As he caressed me I almost died from the pleasure and finally
gasped, "I can't wait longer! NOW NOW!"
He slipped behind me and I felt him behind me. His penis was
much bigger than Stacey and I felt myself stretch to receive him.
He seemed to keep going into me until I felt as though I would
be split in two and my anus felt hot from the stretching. I
gasped and he stopped and then he withdrew slightly and went in
again until I really felt I could take no more and then I felt
his testicles against my bottom.
Justin then slowly stated to make love to me. He pushed my
blouse up and as he pumped in and out he stroked my back and then
reached around and felt my false breasts and then my bliss was
complete as he slipped his hand under me and took hold of my
penis.
Justin seemed to be able to second guess when I was on the verge
of my orgasm and would grip me tightly and not move and then
resume his relentless thrusting until I was crying out for
relief. Then Justin deepened his thrusting and I felt him swell
inside me and with a cry he came and at the same time he brought
me to orgasm and I flooded my panties with my come and we
collapsed together.
Afterwards I felt Sally Anne come across and stroke us both and
kiss first Justin and then me.
Justin slipped out of me and we cuddled together as close friends
and lovers.
I had finally had a true homosexual affair. I lay their in
Justin and Sally Anne's arms and thought about me. I decided I
probably was bisexual as I had loved the sex with Justin and knew
that that would not be the last time but what that had done was
to make me realise how much I loved Sally Anne and how unique and
special our life was.
After Justin left Sally Anne and I changed into pretty nighties
and made love with such tenderness I don't think either of us had
any doubts of our true love for each other.
Chapter 4 - Afterward
I had wondered how things might develop but later that week Sally
Anne came home and said that Justin had left.
He had received a call saying his mother was ill and needed him
and he had taken the next flight to her. Justin never returned
but was always remembered by both of us as a wonderful lover.
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