I visited my new 'girlfriend' again on Saturday 13th June 2026, and stayed overnight alongside her in bed.
My new girlfriend's name is Francesca
Elise, who is a crossdresser like me but needed her visitor to be in male mode to be able to kiss and cuddle him and to be penetrated by him.
I arrived at 14:00 on Saturday 13th June and Francesca was not ready because she had
underestimated the time taken to do a thorough multiple enemas internal
cleaning in preparation for my visit. So I setup my laptop in the lounge, attached the XXX hard drive, and started to play the many XXX Trans videos on a random loop in VLC.
When Francesca came into the room, she looked gorgeous, wearing a
wig, makeup, earrings, a long black and white flowing dress, black hold-up stockings
and high heel shoes, plus Calvin Klein Eternity perfume. I got up to greet her,
kissed her and held her hand as we sat on the sofa in front of the laptop. Then we started kissing and Francesca stroked my cock through my clothing; I took off my shorts and resumed kissing her, and she now had full access to my
cock; we
French kissed deeply and for a prolonged period; I started to fondle
Francesca’s semi-erect clit through her dress, then pulled her dress up and
fondled her clit through her panties; Francesca suggested that I might do a
little more to her now erect clit, the inference being felatio (cunnilingus)
and I got off the sofa, kneeling between her spread legs stocking-clad legs; I
pulled her clit out from her panties and started to lick and suck it, spending
time pleasuring it for her as Francesca watched the XXX video and
enjoyed my attention to her clit; I could taste her precum in my mouth; I said
that I wanted to fuck Francesca, and she got into ‘the position’ on all fours
in front of me; I tried to enter her but Francesca’s cunt entrance was
incredibly tight as she was a virgin; so we moved to the
bedroom intending to have sex on her bed; Francesca covered the bed with a
sheet and put pillows below the sheet to raise her butt; then she lay face
down, butt raised, with her legs spread; I tried several times to enter her and
still found her cunt too tight; so I went back into the lounge to fetch the
three strap-on dildos that I had put into my ‘toys bag’; I put on the smallest
strap-on dildo, applied lubricant to it and pushed more lubricant into
Francesca’s cunt; then I got into position between her legs and slowly inserted
the dildo into her cunt; after a moment her entrance widened
and I progressively inserted the dildo until it was eventually penetrating
Francesca to the hilt; now I could fuck her, gently moving back and forth,
pulling the dildo almost out and then pushing it deep inside her again; Francesca
was now being truly fucked as I started to increase the speed of my thrusting;
it was a perfect scenario, Francesca face down legs spread on the bed, myself
above her and between her legs and my strap-on ‘cock’ rapidly thrusting into
her to the hilt; exactly what Francesca had been anticipating, the only
difference being the dildo being used instead of my cock, which had now become
fully erect; so I withdrew the strap-on dildo and swopped it for my erect cock,
easing my cock into Francesca’s cunt and fucking her; a wonderful
feeling and fulfilling for both of us. I returned to the lounge and sat on the
sofa while Francesca changed her outfit; Francesca returned to the lounge
wearing a pink dress, stockings and pink trainers, and more CK Eternity
perfume; she looked and smelt wonderful; we sat watching the XXX video, the video we were watching was a Petra TV Training video
and Petra was being severely and repeatedly fucked by a man in many positions; Francesca
was calm and relaxed, having just been fucked on the bed; she pulled my
cock out from my briefs and started to masturbate it; all this time we were watching Petra being
dominated and rapidly fucked to the hilt by the man; then Francesca started to suck my cock, and she
performed felatio on me which felt wonderful; Francesca asked me about the wigs I had brought and we
got them out of the box to look at them; Francesca left the room, returned wearing one of the wigs and she looked fantastic in it; we continued to French kiss,
each fondling the other; I pulled her clit out
and pleasured it; I was now wearing a black nightie, black panties and black hold-up stockings; Francesca
accepted this, her ‘boyfriend’ now clothed in female attire, and we kissed
deeply as each of us pleasured the other with our hands, her clit fully erect
and my cock inside my panties also erect; we kissed like this for a long time,
enjoying the post-coital moment; I asked Francesca is she would fuck me and she
said “Yes”, so I moved to ‘the position’, all fours on the floor; Francesca, knelt behind
me and entered me, starting to slowly fuck me with
her erect clit, as I knelt on all fours with my head on the sofa; it felt
wonderful, feeling her large clit penetrating me and thrusting to the hilt
inside me, the pleasure was enormous; I suggested that Francesca use a strap-on dildo
to fuck me, as I had used to fuck her, and Francesca put on the strap-on, inserted the dildo into me and was now fucking me very deep to the hilt; it was
momentarily uncomfortable as the dildo spread my ‘sissy cunt lips’ and also
uncomfortable because of this second dildo was longer than that I had used to
fuck Francesca; but after a while, with her rhythmically thrusting the dildo
into me, I got more and more aroused; Francesca was pleasuring her ‘boyfriend’
by ‘pegging’ him with a long thick strap-on dildo; all I could do was kneel on
all fours and take her thrusting, feeling more and more aroused with each
thrust and getting closer and closer to orgasm; my ‘sissy cunt lips’ were
tightening around the dildo as I got near to cumming, which did not happen but
the feeling was wonderful; Francesca changed her attire into a grey pleated skirt,
and she looked fantastic; I suggested that we might go back to the bedroom to perform 69
felatio on each other; I got on the bed upside down, with my head to the bottom
of the bed, and Francesca lay beside me in the normal position; we lay on our
sides to give access to cock and clit, and we started pleasuring each other
with our mouths; it felt wonderful, being pleasured with felatio, feeling lips
and tongue on my cock as I sucked and licked Francesca’s clit; then Francesca
asked me to use my teeth on her clit as part of pleasuring her; I was surprised
but I did as requested, gently pressing my teeth onto her clit and I moved my
mouth up and down, sucking, and licking
her at the same time, also masturbating her with my hand gripping the shaft of
her clit; Francesca got more and more aroused, thrusting upwards as she lay on
the bed completely ignoring my cock and focussed on receiving pleasure; she
thrust deep into my mouth as I bit her, so deep that I was repeatedly gagging
as her very erect clit hit the back of my throat and threatened to go further
down my windpipe; Francesca obviously enjoyed the feeling of me biting her, as
well as my constant licking and sucking; then I started to taste her precum in
my mouth, savouring it as I moved my flickering tongue over the tip of her
clit; I had not tasted cum for a very long time, for decades, and it tasted
divine; Francesca did not spurt into my mouth, she simply ‘leaked’ cum as she
trust upwards and I sucked and licked her; it was obvious that Francesca would
not actually cum but she had really enjoyed the moment; I asked Francesca if
she could use her teeth on my cock as she performed felatio, because no-one
male or female had ever dragged their pressing teeth up and down my cock;
Francesca did as requested and started to give me felatio, with her lips,
mouth, tongue and teeth; it felt amazing and I was writhing in pleasure, trying
desperately not to cum in Francesca’s mouth (which she had requested on my
first visit to her home); clearly Francesca did not like or had never really
tasted cum, and was reluctant to receive it in her mouth; so I told her that
she had been leaking pre-cum into my mouth while she thrust her clit deep into
it, and while I sucked, licked and bit her clit; I told Francesca that pre-cum
tasted slightly salty and that I actually liked the taste, also telling her
that cum itself was salty; after Francesca had performed her wonderful biting
version of felatio on my cock, she asked me if I was hungry for food and I said
“Yes”, so while Francesca changed into yet another costume, I changed into male attire, took the laptop
and XXX hard disk down to the kitchen and set it up on the table still
playing XXX videos; Francesca had put the pink dress on again with a wig, and she looked
wonderful as she came downstairs and entered the kitchen area; we chatted as
she prepared dinner for us; a salad and a very tasty fish;
we ate and chatted, drank wine and chatted, ate some more and chatted, all an
easy ‘get to know you more' conversation, occasionally interrupted by us
watching a particularly interesting XXX video now showing on the laptop; we
chatted endlessly and pleasantly for hours, finishing off the original Rosé wine
and then a bottle of white wine, then cold beer; because I was stopping the
night this time, there was no need to worry about alcohol or time, which moved
to after midnight and on to beyond two o’clock in the morning when we finally
got up from the table and cleared the plates into the kitchen area; then we sat
on one of the sofas, cuddled and kissed, started to fondle each other and
became aroused again; rather than start sucking cocks and clits in the den,
Francesca suggested that we move up to the bedroom and onto her bed; I put the
laptop and XXX hard disk away, packed the toys in their large bag, prepared my
items for leaving early in the morning, took my
toiletries into the main bathroom and put on my nightie and panties; Francesca
joined me in the bedroom and went into the ensuite to take off her makeup; then
she got into bed with me and we started kissing again, me with both my arms
around her; she started to rub my cock through my panties, then slid my cock
out so that she could grip it with her hand and masturbate it; I moved one hand
down to her clit and did the same thing; then I changed position and started
sucking her clit, biting is as instructed earlier, sucking and licking it;
Francesca almost immediately started thrusting her very erect clit deep into my
mouth, causing me to gag again but this time I could control the gagging;
Francesca’s salty precum started to leak onto my flapping eager tongue and she
continued to leak precum until she started to thrust in earnest into my
recipient mouth; Francesca came in my mouth, not copiously but obviously given
the deepest thrusts were held against my throat; I could feel her salty cum,
not a lot of it but enough to know that she was satisfied; I asked her to
resume sucking and biting my cock, which she did, and that’s how our afternoon
and evening ended, with a very satisfied Francesca and me also being very satisfied
(but not cumming in her mouth); my cum and associated orgasm would have to wait
until I returned home in the morning; it must already have been 3 am and I had
asked for a 7:30 am alarm, so we did not get much sleep but we slept side by
side, my arm around her after briefly fondling her clit through her panties;
when the alarm did sound, even though I needed to go to receive a home
delivery, I couldn’t resist sucking and licking Francesca’s clit again for a
final time on this visit, biting it gently as I gripped and masturbated it with
my hand.
It was time to get up, my bags were almost packed earlier, so it
was just a matter of packing my toiletries and putting on male attire, leaving
without having a shower because I could do that at home; we kissed at the door
in the hallway and I left my fully cross-dressed Francesca inside the doorway
as I said “Bye for now” and walked to my car.
I eagerly await my next ‘boyfriend’ visit to Francesca my
girlfriend, because on my next visit we will take our relationship further; I
have instructed Francesca to train and expand the capacity of her ‘clit lips’
with an anal plug that I had left behind; also for Francesca to install an under mattress restraint system in her bedroom, ready for me to immediately
restrain her, at a time of my choosing on my next visit; Francesca would be face down on her bed
with her spread legs and arms held by the wrist and ankle cuffs of the under
mattress restraint system; then, while Francesca is helpless, I will tease her
sissy cunt with a lubricated finger, insert a range of objects into her,
penetrate her with plugs, dildos and other toys, then fuck her lubricated cunt
first with a strap-on and subsequently with my erect cock; I
will then proceed to fuck Francesca deeply and increasingly more rapid until I
cum inside her, spurting my cum into her helpless sissy cunt; after that
Francesca will need punishing, for being a naughty girl, and I will use my
hand, a whip, a paddle and a riding crop on Francesca’s butt until it is
showing red marks (not blood); I will probably want to lubricate her cunt again
and fuck her to completion again, which will take some time for my second cum. I have
requested weekly overnight visits, on Fridays/Saturdays (moved occasionally to Saturdays/Sundays if necessary).
Until the next visit….
x
