Written by MacsMan
My Introduction to the Bi life
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How I Discovered My Bi Self
After a lifetime of swinging with my wonderful wife she developed a medical condition which realistically ended her wanting or being able to have sex again. What a bummer I know but a man still has needs and I turned to visiting escorts. Wow the variety and availability is possibly as wide as it was in our swinging days. I met with girls barely legal to mature grannies and each and everyone had some wonderful experiences to share with me. Looking through an escort directory I was taken by a stunning red head. Fascinated I read on and discovered she was a Tgirl with all the right equipment in working order. Why not? My curiosity got the better of me and I rang her to arrange a meeting.
My only involvement sexwise with another male had been as a teenager when a mate had to stay over at my parents place where I of course lived. We shared my bed and I was quickly asleep. Sometime later I woke to find my ‘mates’ hand fondling my cock. What the fuck I exclaimed suddenly wide awake. Take your dirty hands off me and go sleep on the floor. Melvin (his name) meekly obeyed and that was my last contact with him. I was not ‘homo’ and what a friend he was, trying to get me to reciprocate and ‘play’ with his dirty cock.
Back to the present time - I had my booking with a Tgirl, a beautiful girl at that l, but one who also had a cock!
Ringing her door bell, there she was 5’11” and wearing a low cut mini dress showing off her wonderful tits (36”E’s), long, long legs, sexy arse and a smile that melted my heart in an instant. Wasting no time after I’d made the payment she had her tongue down my throat playing footsie with my tonsils. My automatic reaction was an immediate and massively hard cock. This girl had my cock out and stripped us both naked. She had my cock in her hot mouth. Wow this girl was hot. Just then I beheld her cock and it was massively impressive even to a 100% heterosexual like me. I was transfixed and couldn’t resist for even a second, tentatively touching, holding and gently stroking it. It was 8” and came with an impressive girth. Still almost in a trancelike state I found my mouth on it, sucking and massaging with my tongue and overwhelmed by the heat, texture, the throbbing veins and that taste it was like nectar.
At that instant I knew that I was now bi sexual. I saw a cock in a new light and understood what my female lovers had got from going down on me. I realised why they had really enjoyed the whole action even swallowing my cum greedily. My Tgirl experience didn’t just end with me enjoying giving head and marvelling at the power, texture, heat, aroma, taste and the thrill of those engorged throbbing veins however. My new lover soon turned me over onto my back, raising my legs over her shoulders and with liberal volumes of lubricant applied opened wide my previously virgin arse with that same cock I’d only minutes earlier had fucking my mouth. It wasn’t exactly painful but I certainly felt this new intrusion in rear. In a very short time her cock was deep in me and started the pistoning action slowly at first and then incrementally faster massaging my prostate and surprisingly causing my cock to spew it’s own manseed forcefully up the length of my still raging hard shaft and ejaculating hotly over my abdomen.
After showering and dressing I left feeling elated and sore. My arse remained sore yet stimulated for days afterwards and I knew I had to have more.
Checking out one of the local social contact websites I saw this guy who was bi curious and I made contact arranging a hookup at a local hotel. Intriguingly he was also into cross dressing and looked really hot dressed like a slutty sex siren complete with wig and fuck me high heels which I found another real turn on, accepting that I too needed to experiment. Sneakily whilst my wife was out with friends I found a pair of her skimpiest panties and slipped them on. Instant hard on and such a sexual boost from the silky smooth touch of the fabric. Next out came one her bras and stuffing the cups full with some socks I managed to get in place. Looking in a mirror I turned and posed stroking my arse and prick which the head protruding and leaking pre cum. Not bad I said quietly to myself. I replaced my wife’s borrowed clothes and straight away ordered some of own online.
In a couple of long weeks my new clobber arrived and I successfully intercepted the post for all of deliveries too. Agonisingly my wife seemed to become house bound for a long, long time. When at last she did leave me alone I eagerly opened and throwing off my man gear I began redressing as a sexy slut. Stockings and suspenders wow. Padded bra and skimpy off the shoulders top, ‘g’ string and see through micro mini skirt showing off my sexy arse and straining to contain my ready to burst cock to maximum effect. I quite fancied myself looking like this.
At last my man date time arrived. Nervously I dressed in my new gear and covered up with normal clothes for the short journey to my ‘date’. Knocking nervously on his door it was quickly opened and I was welcomed inside with a hot kiss and a squeeze of my arse. My date had on his sexy clothes complete with wig and fuck me heels. Introduced now to him in person he asked if he could see my girly clothes and after my nodded agreement he slowly removed my covering of male clothing and straight away fell to his knees and kissed my already hard cock before swallowing much of my manhood deeply in his mouth. He paused and asked if I’d like wear a spare wig he had and I readily agreed watching as he dressed me and groomed my new me. Lipstick he asked and again I keenly accepted his offer to apply on my lips without hesitation. He circled me giving me many compliments and his approval.
Let’s get comfortable on the bed I brazenly said, and we fell to the bed into a passionate embrace of deep French kissing and dry personal fondling. When we broke our kiss I asked if we could have a 69’er. Yes please he answered and he changed ends taking my cock in his mouth at the same instant as I did his. My second cock not as long or as wide fitted well in my mouth and I began to work my magic on this my second cock. Memories of my Tgirl experience came flooding back to me as I enjoyed this new cock entering into my life. Several times my date stopped me fearing he was going to blow his load prematurely. I wouldn’t have minded then feeling him erupt deeply in my willing mouth but he wanted to experience his first top or indeed first male fuck of his life. He rolled onto my hard throbbing cock a condom and with me in a doggie position and my arse ready he lubed me up presenting his cockhead at my arse opening. Slowly but eagerly he was soon fully in me and enthusiastically fucked to his orgasm. It was all over too quickly and I was was a little disappointed. Whether it was the short duration, the smaller cock size, pack of expertise/experience or a combination of any of them I don’t know. He however was quite ecstatic and really like loved both sucking me off and fucking and has has asked for another date which I’m going to accept before I then decide just why his first session was a one off disappointment or indeed my next fuck will satisfy me in a similar manner to my Tgirl.
Meanwhile I’ve also met another and more experienced bi lover who certainly knows how to satisfy me and with whom I’m going to fucking quite regularly. I met him on the same site as my first man date and we both enjoy dressing wearing wigs and high heels. His cock also is a better size larger and fat than date 1 and more comfortable than the Tgirl date. He also is more experienced and when he enters me he straight away hits the areas that soon have all my senses reach peak enthralment and I see lights as my own cock erupts. Sucking him off is also more thrilling and I’ve been privileged to feel him unload his manseed deeply in my mouth and taste his beautiful seed when I’m licking him clean. Hopefully we’ll be seeing more of each other and learning how to pleasure each other in different ways too.
My heterosexual experiences are also at a new high as my g/f and I grow ever closer and we share everything that happens whenever we get together. She just loves hearing of my bi adventures and punishes me whenever I’m really naughty with her slut taking paddle. She always leaves me the word slut glowing on both of buttocks and fucks my brains out as I retell of my latest bi episodes. As for dressing up we share each other’s clothes and each other’s minds and bodies in a relationship made in heaven. That she is 43 years younger never even comes into play. She and I are free to see and fuck others and life is fantastic.
Next week I’ve both a man and girl dates and they promise to be real balls draining fun extraordinary.